activity_comment string | activity_id int64 | assay_chembl_id string | assay_description string | assay_type string | bao_format string | bao_label string | canonical_smiles string | data_validity_comment null | document_chembl_id string | document_journal string | document_year int64 | molecule_chembl_id string | molecule_pref_name string | pchembl_value float64 | potential_duplicate int64 | qudt_units string | record_id int64 | relation string | src_id int64 | standard_flag int64 | standard_relation string | standard_type string | standard_units string | standard_value float64 | target_chembl_id string | target_organism string | target_pref_name string | target_tax_id string | text_value null | type string | units string | uo_units string | value string | ligand_efficiency__bei string | ligand_efficiency__le string | ligand_efficiency__lle string | ligand_efficiency__sei string | availability_type float64 | black_box_warning int64 | chirality int64 | first_approval float64 | helm_notation string | inorganic_flag int64 | max_phase string | molecule_type string | natural_product int64 | oral bool | parenteral bool | polymer_flag int64 | pref_name string | prodrug int64 | structure_type string | therapeutic_flag bool | topical bool | usan_stem string | usan_year float64 | withdrawn_flag bool | molecule_structures__canonical_smiles string | molecule_structures__molfile string | molecule_structures__standard_inchi string | molecule_structures__standard_inchi_key string | molecule_properties__alogp float64 | molecule_properties__aromatic_rings float64 | molecule_properties__full_molformula string | molecule_properties__full_mwt string | molecule_properties__hba float64 | molecule_properties__hbd float64 | molecule_properties__heavy_atoms float64 | molecule_properties__mw_freebase float64 | molecule_properties__np_likeness_score string | molecule_properties__num_ro5_violations float64 | molecule_properties__psa float64 | molecule_properties__qed_weighted float64 | molecule_properties__ro3_pass string | molecule_properties__rtb float64 | molecule_hierarchy__active_chembl_id string | molecule_hierarchy__molecule_chembl_id string | molecule_hierarchy__parent_chembl_id string | molecule_synonyms_flat string | cross_references_flat string | assay_category null | assay_cell_type string | assay_organism string | assay_strain string | assay_subcellular_fraction string | assay_tax_id float64 | assay_tissue string | assay_type_assay string | assay_type_description string | bao_format_assay string | bao_label_assay string | cell_chembl_id string | confidence_description string | confidence_score int64 | description string | document_chembl_id_assay string | relationship_description string | relationship_type string | src_assay_id null | src_id_assay int64 | target_chembl_id_assay string | tissue_chembl_id string | variant_sequence null | assay_parameters_flat string | target_organism_enriched string | target_pref_name_enriched string | species_group_flag bool | target_type string | tax_id float64 | uniprot_accession string | component_description string | component_type string | component_id float64 | n_components float64 | mechanism_of_action string | action_type string | direct_interaction float64 | disease_efficacy float64 | mechanism_comment string | selectivity_comment string | binding_site_comment string | mesh_headings string | efo_terms string | max_phase_for_ind string | n_indications float64 | doc__abstract string | doc__authors string | doc__doi string | doc__doi_chembl null | doc__first_page string | doc__issue string | doc__journal string | doc__patent_id null | doc__pubmed_id float64 | doc__src_id int64 | doc__title string | doc__volume string | doc__year int64 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
null | 40,611 | CHEMBL750936 | In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 10 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein | B | BAO_0000219 | cell-based format | Nc1nc(OCc2ccccc2)c2nc[nH]c2n1 | null | CHEMBL1136584 | Bioorg Med Chem Lett | 2,003 | CHEMBL407874 | 6-O-BENZYLGUANINE | null | 0 | null | 309,926 | = | 1 | 0 | = | Activity | (fM of O6-MeG removed) (mg of protein)-1 | 50 | CHEMBL2864 | Homo sapiens | Methylated-DNA--protein-cysteine methyltransferase | 9606 | null | Activity | (fM of O6-MeG removed) (mg of protein)-1 | null | 50.0 | null | null | null | null | null | 0 | 2 | null | null | 0 | 3.0 | Small molecule | 1 | false | false | 0 | 6-O-BENZYLGUANINE | 0 | MOL | false | false | null | null | false | Nc1nc(OCc2ccccc2)c2nc[nH]c2n1 |
RDKit 2D
18 20 0 0 0 0 0 0 0 0999 V2000
0.6696 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3841 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 -0.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 0.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 0.9993 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 -0.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5440 0.7443 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5440 2.0792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3841 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3841 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 -3.1257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7594 0.9993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0289 1.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7594 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
1 5 2 0
1 11 1 0
4 3 1 0
6 3 1 0
4 5 1 0
16 4 2 0
6 8 1 0
16 7 1 0
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8 15 1 0
17 9 1 0
18 9 1 0
10 12 1 0
18 11 2 0
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13 14 1 0
14 15 2 0
16 18 1 0
M END
> <chembl_id>
CHEMBL407874
> <chembl_pref_name>
6-O-BENZYLGUANINE | InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17) | KRWMERLEINMZFT-UHFFFAOYSA-N | 1.51 | 3 | C12H11N5O | 241.25 | 5 | 2 | 18 | 241.25 | -0.67 | 0 | 89.71 | 0.73 | N | 3 | CHEMBL407874 | CHEMBL407874 | CHEMBL407874 | 6-o-benzylguanine [OTHER] | NSC-637037 [RESEARCH_CODE] | O6-benzylguanine [OTHER] | O(6)-benzylguanine [OTHER] | null | null | MCF7 | null | null | null | null | null | B | Binding | BAO_0000219 | cell-based format | CHEMBL3308403 | Homologous single protein target assigned | 8 | In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 10 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein | CHEMBL1136584 | Homologous protein target assigned | H | null | 1 | CHEMBL2864 | null | null | null | Homo sapiens | Methylated-DNA--protein-cysteine methyltransferase | false | SINGLE PROTEIN | 9,606 | P16455 | Methylated-DNA--protein-cysteine methyltransferase | PROTEIN | 1,194 | 1 | null | null | null | null | null | null | null | Melanoma | Glioblastoma | Lymphoma | Neoplasms | Sarcoma | Multiple Myeloma | Lymphoma, T-Cell, Cutaneous | Sezary Syndrome | Mycosis Fungoides | Gliosarcoma | Central Nervous System Neoplasms | Colorectal Neoplasms | cutaneous melanoma | glioblastoma multiforme | lymphoma | neoplasm | sarcoma | multiple myeloma | Cutaneous T-cell lymphoma | Sezary's disease | mycosis fungoides | gliosarcoma | Central Nervous System Neoplasm | colorectal cancer | 3.0 | 12 | Novel radiolabeled O(6)-benzylguanine derivatives, 6-O-[(11)C]-[(methoxymethyl)benzyl]guanines ([(11)C]p-O(6)-MMBG, 1a; [(11)C]m-O(6)-MMBG, 1b; ([(11)C]o-O(6)-MMBG, 1c), have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents for DNA repair protein, O(6)-alkylguanine-DNA alkyltransferase (AGT). | Liu X, Zheng QH, Fei X, Wang JQ, Ohannesian DW, Erickson LC, Stone KL, Hutchins GD. | 10.1016/s0960-894x(02)01048-x | null | 641 | 4 | Bioorg Med Chem Lett | null | 12,639,548 | 1 | Synthesis and preliminary biological evaluation of 6-O-[11C]-[(methoxymethyl)benzyl]guanines, new potential PET breast cancer imaging agents for the DNA repair protein AGT. | 13 | 2,003 |
null | 40,612 | CHEMBL713457 | In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 50 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein | B | BAO_0000219 | cell-based format | Nc1nc(OCc2ccccc2)c2nc[nH]c2n1 | null | CHEMBL1136584 | Bioorg Med Chem Lett | 2,003 | CHEMBL407874 | 6-O-BENZYLGUANINE | null | 0 | null | 309,926 | = | 1 | 0 | = | Activity | (fM of O6-MeG removed) (mg of protein)-1 | 19 | CHEMBL2864 | Homo sapiens | Methylated-DNA--protein-cysteine methyltransferase | 9606 | null | Activity | (fM of O6-MeG removed) (mg of protein)-1 | null | 19.0 | null | null | null | null | null | 0 | 2 | null | null | 0 | 3.0 | Small molecule | 1 | false | false | 0 | 6-O-BENZYLGUANINE | 0 | MOL | false | false | null | null | false | Nc1nc(OCc2ccccc2)c2nc[nH]c2n1 |
RDKit 2D
18 20 0 0 0 0 0 0 0 0999 V2000
0.6696 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3841 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 -0.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 0.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 0.9993 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 -0.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5440 0.7443 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5440 2.0792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3841 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 2.2368 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3841 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6696 -3.1257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 -2.7132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0449 -1.8882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7594 0.9993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0289 1.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7594 1.8243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
1 5 2 0
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6 8 1 0
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18 11 2 0
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13 14 1 0
14 15 2 0
16 18 1 0
M END
> <chembl_id>
CHEMBL407874
> <chembl_pref_name>
6-O-BENZYLGUANINE | InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17) | KRWMERLEINMZFT-UHFFFAOYSA-N | 1.51 | 3 | C12H11N5O | 241.25 | 5 | 2 | 18 | 241.25 | -0.67 | 0 | 89.71 | 0.73 | N | 3 | CHEMBL407874 | CHEMBL407874 | CHEMBL407874 | 6-o-benzylguanine [OTHER] | NSC-637037 [RESEARCH_CODE] | O6-benzylguanine [OTHER] | O(6)-benzylguanine [OTHER] | null | null | MCF7 | null | null | null | null | null | B | Binding | BAO_0000219 | cell-based format | CHEMBL3308403 | Homologous single protein target assigned | 8 | In vitro inhibitory activity of compound against AGT (O6-alkylguanine-DNA alkyltransferase) at a concentration of 50 uM using breast cancer MCF-7 cells, expressed as Fmol O6-MeG removed/mg of protein | CHEMBL1136584 | Homologous protein target assigned | H | null | 1 | CHEMBL2864 | null | null | null | Homo sapiens | Methylated-DNA--protein-cysteine methyltransferase | false | SINGLE PROTEIN | 9,606 | P16455 | Methylated-DNA--protein-cysteine methyltransferase | PROTEIN | 1,194 | 1 | null | null | null | null | null | null | null | Melanoma | Glioblastoma | Lymphoma | Neoplasms | Sarcoma | Multiple Myeloma | Lymphoma, T-Cell, Cutaneous | Sezary Syndrome | Mycosis Fungoides | Gliosarcoma | Central Nervous System Neoplasms | Colorectal Neoplasms | cutaneous melanoma | glioblastoma multiforme | lymphoma | neoplasm | sarcoma | multiple myeloma | Cutaneous T-cell lymphoma | Sezary's disease | mycosis fungoides | gliosarcoma | Central Nervous System Neoplasm | colorectal cancer | 3.0 | 12 | Novel radiolabeled O(6)-benzylguanine derivatives, 6-O-[(11)C]-[(methoxymethyl)benzyl]guanines ([(11)C]p-O(6)-MMBG, 1a; [(11)C]m-O(6)-MMBG, 1b; ([(11)C]o-O(6)-MMBG, 1c), have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents for DNA repair protein, O(6)-alkylguanine-DNA alkyltransferase (AGT). | Liu X, Zheng QH, Fei X, Wang JQ, Ohannesian DW, Erickson LC, Stone KL, Hutchins GD. | 10.1016/s0960-894x(02)01048-x | null | 641 | 4 | Bioorg Med Chem Lett | null | 12,639,548 | 1 | Synthesis and preliminary biological evaluation of 6-O-[11C]-[(methoxymethyl)benzyl]guanines, new potential PET breast cancer imaging agents for the DNA repair protein AGT. | 13 | 2,003 |
null | 40,613 | CHEMBL857692 | Inhibitory concentration against HCV NS3 protease was determined | B | BAO_0000357 | single protein format | CC[C@H](NC(=O)[C@H](CC1CCCCC1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)c1cnccn1)[C@@H](C)CC)C(=O)C(=O)N[C@H](C(=O)O)C(C)C | null | CHEMBL1136650 | Bioorg Med Chem Lett | 2,003 | CHEMBL13442 | null | 5.44 | 0 | http://www.openphacts.org/units/Nanomolar | 12,748 | = | 1 | 1 | = | IC50 | nM | 3,600 | CHEMBL4620 | Hepatitis C virus genotype 1a (isolate 1) (HCV) | Genome polyprotein | 11104 | null | IC50 | uM | UO_0000065 | 3.6 | 7.60 | 0.15 | 3.14 | 2.41 | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CC[C@H](NC(=O)[C@H](CC1CCCCC1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)c1cnccn1)[C@@H](C)CC)C(=O)C(=O)N[C@H](C(=O)O)C(C)C |
RDKit 2D
51 52 0 0 1 0 0 0 0 0999 V2000
9.0417 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.3250 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0375 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.7542 -3.1667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.6042 -3.1667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.8917 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.2583 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.1792 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.7542 -3.5792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.4667 -3.5792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.8917 -3.1667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.3250 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9750 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.4667 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4667 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1792 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.6125 -3.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.1875 -3.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6958 -3.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
8.3250 -2.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
9.0417 -4.4042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.0375 -2.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
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1.1792 -2.3417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3250 -4.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.4750 -4.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.9000 -3.5792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
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5.8750 -1.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.6125 -4.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.7000 -1.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4542 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.1875 -1.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.3250 -4.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0417 -5.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.8667 -0.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.1042 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.6917 -0.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
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15 26 1 1
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16 29 1 1
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49 44 1 0
50 43 1 0
51 49 1 0
51 50 1 0
38 36 2 0
M END
> <chembl_id>
CHEMBL13442
> <chembl_pref_name>
None | InChI=1S/C36H57N7O8/c1-8-22(7)29(43-32(46)25(17-20(3)4)40-33(47)27-19-37-15-16-38-27)34(48)41-26(18-23-13-11-10-12-14-23)31(45)39-24(9-2)30(44)35(49)42-28(21(5)6)36(50)51/h15-16,19-26,28-29H,8-14,17-18H2,1-7H3,(H,39,45)(H,40,47)(H,41,48)(H,42,49)(H,43,46)(H,50,51)/t22-,24-,25-,26-,28-,29-/m0/s1 | DIROIABUGPDKJH-HPWCXNRPSA-N | 2.3 | 1 | C36H57N7O8 | 715.89 | 9 | 6 | 51 | 715.89 | -0.19 | 2 | 225.65 | 0.11 | N | 20 | CHEMBL13442 | CHEMBL13442 | CHEMBL13442 | null | null | null | null | null | null | null | null | null | B | Binding | BAO_0000357 | single protein format | null | Homologous single protein target assigned | 8 | Inhibitory concentration against HCV NS3 protease was determined | CHEMBL1136650 | Homologous protein target assigned | H | null | 1 | CHEMBL4620 | null | null | null | Hepatitis C virus genotype 1a (isolate 1) (HCV) | Genome polyprotein | false | SINGLE PROTEIN | 11,104 | P26664 | Genome polyprotein | PROTEIN | 5,042 | 1 | null | null | null | null | null | null | null | null | null | null | null | Using a tetrapeptide-based alpha-ketoamide template, various amines and amino acids were incorporated to explore the prime side of the HCV NS3 protease catalytic site. Glycine carboxylic acid was found to be the most effective prime group. Further optimization yielded an inhibitor with IC(50) of 0.060 microM. | Han W, Hu Z, Jiang X, Wasserman ZR, Decicco CP. | 10.1016/s0960-894x(03)00031-3 | null | 1111 | 6 | Bioorg Med Chem Lett | null | 12,643,923 | 1 | Glycine alpha-ketoamides as HCV NS3 protease inhibitors. | 13 | 2,003 |
null | 40,615 | CHEMBL615267 | Inhibitory activity against inosine 5'-inosine monophosphate dehydrogenase type II (IMPDH II) | B | BAO_0000357 | single protein format | Nc1ccc2cnccc2c1Br | null | CHEMBL1136691 | Bioorg Med Chem Lett | 2,003 | CHEMBL27011 | null | 6.26 | 0 | http://www.openphacts.org/units/Nanomolar | 39,739 | = | 1 | 1 | = | IC50 | nM | 550 | CHEMBL2002 | Homo sapiens | Inosine-5'-monophosphate dehydrogenase 2 | 9606 | null | IC50 | uM | UO_0000065 | 0.55 | 28.06 | 0.71 | 3.68 | 16.09 | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Nc1ccc2cnccc2c1Br |
RDKit 2D
12 13 0 0 0 0 0 0 0 0999 V2000
0.4542 0.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.2583 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1750 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6708 1.5208 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.2500 1.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.1750 1.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4625 1.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4500 -0.5417 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
1.8875 0.2833 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.9625 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.9625 0.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.6708 0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
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8 1 1 0
9 3 1 0
10 5 1 0
11 2 1 0
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5 7 1 0
10 4 2 0
M END
> <chembl_id>
CHEMBL27011
> <chembl_pref_name>
None | InChI=1S/C9H7BrN2/c10-9-7-3-4-12-5-6(7)1-2-8(9)11/h1-5H,11H2 | JDEBLBVBKMBILY-UHFFFAOYSA-N | 2.58 | 2 | C9H7BrN2 | 223.07 | 2 | 1 | 12 | 223.07 | -0.61 | 0 | 38.91 | 0.7 | Y | 0 | CHEMBL27011 | CHEMBL27011 | CHEMBL27011 | null | null | null | null | null | null | null | null | null | B | Binding | BAO_0000357 | single protein format | null | Homologous single protein target assigned | 8 | Inhibitory activity against inosine 5'-inosine monophosphate dehydrogenase type II (IMPDH II) | CHEMBL1136691 | Homologous protein target assigned | H | null | 1 | CHEMBL2002 | null | null | null | Homo sapiens | Inosine-5'-monophosphate dehydrogenase 2 | false | SINGLE PROTEIN | 9,606 | P12268 | Inosine-5'-monophosphate dehydrogenase 2 | PROTEIN | 333 | 1 | null | null | null | null | null | null | null | null | null | null | null | Screening of our in-house compound collection led to the discovery of 5-bromo-6-amino-2-isoquinoline 1 as a weak inhibitor of IMPDH. Subsequent optimization of 1 afforded a series of novel 2-isoquinolinoaminooxazole-based inhibitors, represented by 17, with single-digit nanomolar potency against the enzyme. | Chen P, Norris D, Haslow KD, Murali Dhar TG, Pitts WJ, Watterson SH, Cheney DL, Bassolino DA, Fleener CA, Rouleau KA, Hollenbaugh DL, Townsend RM, Barrish JC, Iwanowicz EJ. | 10.1016/s0960-894x(03)00107-0 | null | 1345 | 7 | Bioorg Med Chem Lett | null | 12,657,279 | 1 | Identification of novel and potent isoquinoline aminooxazole-based IMPDH inhibitors. | 13 | 2,003 |
null | 40,616 | CHEMBL761409 | Ability to displace [3H]oxytocin from human OT receptor (hOT) | B | BAO_0000357 | single protein format | Cc1cc2cc(C(=O)N3CCC(N4C(=O)OCc5ccccc54)CC3)ccc2[nH]1 | null | CHEMBL1135944 | Bioorg Med Chem Lett | 2,002 | CHEMBL32740 | null | 6.9 | 0 | http://www.openphacts.org/units/Nanomolar | 45,869 | = | 1 | 1 | = | Ki | nM | 125.89 | CHEMBL2049 | Homo sapiens | Oxytocin receptor | 9606 | null | Log Ki | null | UO_0000065 | -6.9 | 17.72 | 0.32 | 2.66 | 10.51 | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Cc1cc2cc(C(=O)N3CCC(N4C(=O)OCc5ccccc54)CC3)ccc2[nH]1 |
RDKit 2D
29 33 0 0 0 0 0 0 0 0999 V2000
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5.4000 -0.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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3.2542 0.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.5417 0.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL32740
> <chembl_pref_name>
None | InChI=1S/C23H23N3O3/c1-15-12-18-13-16(6-7-20(18)24-15)22(27)25-10-8-19(9-11-25)26-21-5-3-2-4-17(21)14-29-23(26)28/h2-7,12-13,19,24H,8-11,14H2,1H3 | CBFKPANXJWRIIF-UHFFFAOYSA-N | 4.24 | 3 | C23H23N3O3 | 389.45 | 3 | 1 | 29 | 389.45 | -0.97 | 0 | 65.64 | 0.71 | N | 2 | CHEMBL32740 | CHEMBL32740 | CHEMBL32740 | null | null | null | null | null | null | null | null | null | B | Binding | BAO_0000357 | single protein format | null | Homologous single protein target assigned | 8 | Ability to displace [3H]oxytocin from human OT receptor (hOT) | CHEMBL1135944 | Homologous protein target assigned | H | null | 1 | CHEMBL2049 | null | null | null | Homo sapiens | Oxytocin receptor | false | SINGLE PROTEIN | 9,606 | P30559 | Oxytocin receptor | PROTEIN | 389 | 1 | null | null | null | null | null | null | null | null | null | null | null | Studies to discover novel, potent and selective oxytocin antagonists are reported. Combinatorial libraries designed to find novel replacements of fragments of oxytocin antagonist L-371,257, identified pyrimidine, thiazole, indole and benzofuran as potential alternatives to the benzoic acid moiety of L-371,257. Additional investigations identified indole and benzofuran derivatives with potent oxytocin antagonist activity. | Wyatt PG, Allen MJ, Chilcott J, Foster A, Livermore DG, Mordaunt JE, Scicinski J, Woollard PM. | 10.1016/s0960-894x(02)00159-2 | null | 1399 | 10 | Bioorg Med Chem Lett | null | 11,992,786 | 1 | Identification of potent and selective oxytocin antagonists. Part 1: indole and benzofuran derivatives. | 12 | 2,002 |
null | 40,617 | CHEMBL808229 | Minimum fungicidal concentration against Saccharomyces cerevisiae(no antifungal activity) | F | BAO_0000218 | organism-based format | CCCCCCCCOC(=O)c1cccc(O)c1 | null | CHEMBL1134164 | Bioorg Med Chem Lett | 2,001 | CHEMBL117843 | null | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 222,259 | = | 1 | 0 | = | MIC | ug.mL-1 | null | CHEMBL361 | Saccharomyces cerevisiae | Saccharomyces cerevisiae | 4932 | null | MIC | ug ml-1 | UO_0000274 | null | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCCCCOC(=O)c1cccc(O)c1 |
RDKit 2D
18 18 0 0 0 0 0 0 0 0999 V2000
2.9375 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4042 -2.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8792 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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15 17 1 0
16 12 1 0
17 16 1 0
18 13 1 0
10 5 2 0
M END
> <chembl_id>
CHEMBL117843
> <chembl_pref_name>
None | InChI=1S/C15H22O3/c1-2-3-4-5-6-7-11-18-15(17)13-9-8-10-14(16)12-13/h8-10,12,16H,2-7,11H2,1H3 | LAJACIZEQBXWOS-UHFFFAOYSA-N | 3.91 | 1 | C15H22O3 | 250.34 | 3 | 1 | 18 | 250.34 | 0.16 | 0 | 46.53 | 0.56 | N | 8 | CHEMBL117843 | CHEMBL117843 | CHEMBL117843 | null | null | null | null | Saccharomyces cerevisiae | null | null | 4,932 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Minimum fungicidal concentration against Saccharomyces cerevisiae(no antifungal activity) | CHEMBL1134164 | Non-molecular target assigned | N | null | 1 | CHEMBL361 | null | null | null | Saccharomyces cerevisiae | Saccharomyces cerevisiae | false | ORGANISM | 4,932 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Octyl gallate (3,4,5-trihydroxybenzoate) was found to possess antifungal activity against Saccharomyces cerevisiae and Zygosaccharomyces bailii, in addition to its potent antioxidant activity. Catechol moiety is essential to elicit this activity. The primary fungicidal activity of octyl gallate comes from its ability to act as a nonionic surface-active agent (surfactant). The length of the alkyl chain is not a major contributor but plays an important role in eliciting the activity. | Kubo I, Xiao P, Fujita K. | 10.1016/s0960-894x(00)00656-9 | null | 347 | 3 | Bioorg Med Chem Lett | null | 11,212,107 | 1 | Antifungal activity of octyl gallate: structural criteria and mode of action. | 11 | 2,001 |
null | 40,618 | CHEMBL763559 | Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP) | F | BAO_0000218 | organism-based format | CCCCNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1 | null | CHEMBL1133917 | Bioorg Med Chem Lett | 2,001 | CHEMBL71066 | null | 7.7 | 0 | http://www.openphacts.org/units/Nanomolar | 123,884 | = | 1 | 1 | = | IC50 | nM | 20 | CHEMBL372 | Homo sapiens | Homo sapiens | 9606 | null | IC50 | uM | UO_0000065 | 0.02 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1 |
RDKit 2D
27 28 0 0 0 0 0 0 0 0999 V2000
3.0542 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5792 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-1.1333 -2.6500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.3667 -2.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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6.6917 -2.7125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-1.1250 -1.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-1.1208 0.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
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M END
> <chembl_id>
CHEMBL71066
> <chembl_pref_name>
None | InChI=1S/C19H26N4O4/c1-2-3-9-22-19(20)14-6-4-13(5-7-14)16-11-15(27-23-16)12-17(24)21-10-8-18(25)26/h4-7,15H,2-3,8-12H2,1H3,(H2,20,22)(H,21,24)(H,25,26) | WFZZJCOUKAUMBN-UHFFFAOYSA-N | 1.88 | 1 | C19H26N4O4 | 374.44 | 5 | 4 | 27 | 374.44 | -0.61 | 0 | 123.87 | 0.28 | N | 10 | CHEMBL71066 | CHEMBL71066 | CHEMBL71066 | null | null | null | null | Homo sapiens | null | null | 9,606 | Plasma | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP) | CHEMBL1133917 | Non-molecular target assigned | N | null | 1 | CHEMBL372 | CHEMBL3559721 | null | null | Homo sapiens | Homo sapiens | false | ORGANISM | 9,606 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Selective antagonism of the platelet GPIIb/IIIa receptor represents an attractive mechanism for the prevention and treatment of a number of thrombotic disease states. The antiplatelet activity of the oral GPIIb/IIIa receptor antagonists DMP 754 and DMP 802 have been disclosed. In this paper, the synthesis and biological evaluation of a series of potent N-substituted benzamidine isoxazolines are explored. The effect of benzamidine substitution on the duration of antiplatelet efficacy in dog is presented. | Sielecki TM, Liu J, Mousa SA, Racanelli AL, Hausner EA, Wexler RR, Olson RE. | 10.1016/s0960-894x(01)00406-1 | null | 2201 | 16 | Bioorg Med Chem Lett | null | 11,514,170 | 1 | Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists. | 11 | 2,001 |
null | 40,619 | CHEMBL763559 | Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP) | F | BAO_0000218 | organism-based format | COc1ccccc1CNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1 | null | CHEMBL1133917 | Bioorg Med Chem Lett | 2,001 | CHEMBL71111 | null | 7.5 | 0 | http://www.openphacts.org/units/Nanomolar | 123,888 | = | 1 | 1 | = | IC50 | nM | 32 | CHEMBL372 | Homo sapiens | Homo sapiens | 9606 | null | IC50 | uM | UO_0000065 | 0.032 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | COc1ccccc1CNC(=N)c1ccc(C2=NOC(CC(=O)NCCC(=O)O)C2)cc1 |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
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-1.1125 0.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5292 0.1958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-1.9458 0.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL71111
> <chembl_pref_name>
None | InChI=1S/C23H26N4O5/c1-31-20-5-3-2-4-17(20)14-26-23(24)16-8-6-15(7-9-16)19-12-18(32-27-19)13-21(28)25-11-10-22(29)30/h2-9,18H,10-14H2,1H3,(H2,24,26)(H,25,28)(H,29,30) | HTKQOPDYLSNJQL-UHFFFAOYSA-N | 2.28 | 2 | C23H26N4O5 | 438.48 | 6 | 4 | 32 | 438.48 | -0.74 | 0 | 133.1 | 0.33 | N | 10 | CHEMBL71111 | CHEMBL71111 | CHEMBL71111 | null | null | null | null | Homo sapiens | null | null | 9,606 | Plasma | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Concentration required for maximal in vitro inhibition of aggregation of human platelet rich plasma (hPRP) | CHEMBL1133917 | Non-molecular target assigned | N | null | 1 | CHEMBL372 | CHEMBL3559721 | null | null | Homo sapiens | Homo sapiens | false | ORGANISM | 9,606 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Selective antagonism of the platelet GPIIb/IIIa receptor represents an attractive mechanism for the prevention and treatment of a number of thrombotic disease states. The antiplatelet activity of the oral GPIIb/IIIa receptor antagonists DMP 754 and DMP 802 have been disclosed. In this paper, the synthesis and biological evaluation of a series of potent N-substituted benzamidine isoxazolines are explored. The effect of benzamidine substitution on the duration of antiplatelet efficacy in dog is presented. | Sielecki TM, Liu J, Mousa SA, Racanelli AL, Hausner EA, Wexler RR, Olson RE. | 10.1016/s0960-894x(01)00406-1 | null | 2201 | 16 | Bioorg Med Chem Lett | null | 11,514,170 | 1 | Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists. | 11 | 2,001 |
null | 40,620 | CHEMBL812612 | Inhibitory concentration against potent thrombin receptor-1 (PAR-1) on human platelets | B | BAO_0000019 | assay format | CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21 | null | CHEMBL1133830 | Bioorg Med Chem Lett | 2,001 | CHEMBL97952 | null | 6.45 | 0 | http://www.openphacts.org/units/Nanomolar | 179,190 | = | 1 | 1 | = | IC50 | nM | 359 | CHEMBL3974 | Homo sapiens | Proteinase-activated receptor 1 | 9606 | null | IC50 | nM | UO_0000065 | 359.0 | 14.80 | 0.28 | 0.53 | 9.08 | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21 |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
2.0292 -2.7250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5042 -3.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0292 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.2417 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2417 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4042 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0417 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8542 0.5833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2792 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7917 -0.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0875 -1.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3375 -3.3875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.4917 1.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.2125 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6417 -2.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.1125 1.3708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.8167 -4.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5250 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5250 -4.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2250 1.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7417 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7667 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4667 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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1.6792 0.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3917 -5.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1792 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1875 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1875 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7625 -6.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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6 11 1 0
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8 7 1 0
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15 7 1 0
16 6 1 0
17 13 2 0
18 8 1 0
19 3 1 0
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22 15 1 0
23 15 1 0
24 16 1 0
25 16 1 0
26 16 1 0
27 15 1 0
28 19 1 0
29 28 1 0
30 31 2 0
31 20 1 0
32 29 1 0
3 5 1 0
21 30 1 0
8 6 2 0
M END
> <chembl_id>
CHEMBL97952
> <chembl_pref_name>
None | InChI=1S/C27H37N3O2/c1-8-9-14-29-21-12-10-11-13-22(21)30(25(29)28)17-23(31)18-15-19(26(2,3)4)24(32)20(16-18)27(5,6)7/h10-13,15-16,28,32H,8-9,14,17H2,1-7H3 | WWLIKMQMTCGMJV-UHFFFAOYSA-N | 5.91 | 3 | C27H37N3O2 | 435.61 | 5 | 2 | 32 | 435.61 | -0.54 | 1 | 71.01 | 0.47 | N | 6 | CHEMBL97952 | CHEMBL97952 | CHEMBL97952 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | B | Binding | BAO_0000019 | assay format | null | Direct single protein target assigned | 9 | Inhibitory concentration against potent thrombin receptor-1 (PAR-1) on human platelets | CHEMBL1133830 | Direct protein target assigned | D | null | 1 | CHEMBL3974 | null | null | null | Homo sapiens | Proteinase-activated receptor 1 | false | SINGLE PROTEIN | 9,606 | P25116 | Proteinase-activated receptor 1 | PROTEIN | 2,293 | 1 | null | null | null | null | null | null | null | null | null | null | null | Several benzimidazole derivatives have been identified as potent thrombin receptor (PAR-1) antagonists as represented by compound 1h, which showed an IC(50) of 33 nM. | Chackalamannil S, Doller D, Eagen K, Czarniecki M, Ahn HS, Foster CJ, Boykow G. | 10.1016/s0960-894x(01)00555-8 | null | 2851 | 21 | Bioorg Med Chem Lett | null | 11,597,414 | 1 | Potent, low molecular weight thrombin receptor antagonists. | 11 | 2,001 |
null | 40,621 | CHEMBL699495 | Inhibition of human platelet aggregation induced by high affinity thrombin receptor agonist peptide( ha-TRAP) | F | BAO_0000218 | organism-based format | CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21 | null | CHEMBL1133830 | Bioorg Med Chem Lett | 2,001 | CHEMBL97952 | null | 6.08 | 0 | http://www.openphacts.org/units/Nanomolar | 179,190 | = | 1 | 1 | = | IC50 | nM | 825 | CHEMBL372 | Homo sapiens | Homo sapiens | 9606 | null | IC50 | nM | UO_0000065 | 825.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21 |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
2.0292 -2.7250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5042 -3.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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1.2417 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2417 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4042 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0417 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8542 0.5833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2792 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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3.3375 -3.3875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.4917 1.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.2125 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6417 -2.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.1125 1.3708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.8167 -4.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5250 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5250 -4.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2250 1.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7417 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7667 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4667 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1667 -0.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.6792 0.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3917 -5.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1792 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1875 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1875 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7625 -6.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 2 1 0
4 1 1 0
5 4 1 0
6 11 1 0
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8 7 1 0
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29 28 1 0
30 31 2 0
31 20 1 0
32 29 1 0
3 5 1 0
21 30 1 0
8 6 2 0
M END
> <chembl_id>
CHEMBL97952
> <chembl_pref_name>
None | InChI=1S/C27H37N3O2/c1-8-9-14-29-21-12-10-11-13-22(21)30(25(29)28)17-23(31)18-15-19(26(2,3)4)24(32)20(16-18)27(5,6)7/h10-13,15-16,28,32H,8-9,14,17H2,1-7H3 | WWLIKMQMTCGMJV-UHFFFAOYSA-N | 5.91 | 3 | C27H37N3O2 | 435.61 | 5 | 2 | 32 | 435.61 | -0.54 | 1 | 71.01 | 0.47 | N | 6 | CHEMBL97952 | CHEMBL97952 | CHEMBL97952 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Inhibition of human platelet aggregation induced by high affinity thrombin receptor agonist peptide( ha-TRAP) | CHEMBL1133830 | Non-molecular target assigned | N | null | 1 | CHEMBL372 | null | null | null | Homo sapiens | Homo sapiens | false | ORGANISM | 9,606 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Several benzimidazole derivatives have been identified as potent thrombin receptor (PAR-1) antagonists as represented by compound 1h, which showed an IC(50) of 33 nM. | Chackalamannil S, Doller D, Eagen K, Czarniecki M, Ahn HS, Foster CJ, Boykow G. | 10.1016/s0960-894x(01)00555-8 | null | 2851 | 21 | Bioorg Med Chem Lett | null | 11,597,414 | 1 | Potent, low molecular weight thrombin receptor antagonists. | 11 | 2,001 |
null | 40,622 | CHEMBL699496 | Inhibition of human platelet aggregation induced by thrombin | F | BAO_0000218 | organism-based format | CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21 | null | CHEMBL1133830 | Bioorg Med Chem Lett | 2,001 | CHEMBL97952 | null | 5 | 0 | http://www.openphacts.org/units/Nanomolar | 179,190 | = | 1 | 1 | = | IC50 | nM | 10,000 | CHEMBL372 | Homo sapiens | Homo sapiens | 9606 | null | IC50 | nM | UO_0000065 | 10000.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCn1c(=N)n(CC(=O)c2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)c2ccccc21 |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
2.0292 -2.7250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5042 -3.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0292 -4.0542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.2417 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2417 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4042 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0417 0.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8542 0.5833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2792 -1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -0.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7917 -0.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0875 -1.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3375 -3.3875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.4917 1.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.2125 0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6417 -2.3792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.1125 1.3708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.8167 -4.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5250 -2.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5250 -4.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2250 1.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7417 1.8083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7667 -0.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4667 0.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1667 -0.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.6792 0.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3917 -5.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1792 -6.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1875 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1875 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7625 -6.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 2 1 0
4 1 1 0
5 4 1 0
6 11 1 0
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8 7 1 0
9 1 1 0
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23 15 1 0
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28 19 1 0
29 28 1 0
30 31 2 0
31 20 1 0
32 29 1 0
3 5 1 0
21 30 1 0
8 6 2 0
M END
> <chembl_id>
CHEMBL97952
> <chembl_pref_name>
None | InChI=1S/C27H37N3O2/c1-8-9-14-29-21-12-10-11-13-22(21)30(25(29)28)17-23(31)18-15-19(26(2,3)4)24(32)20(16-18)27(5,6)7/h10-13,15-16,28,32H,8-9,14,17H2,1-7H3 | WWLIKMQMTCGMJV-UHFFFAOYSA-N | 5.91 | 3 | C27H37N3O2 | 435.61 | 5 | 2 | 32 | 435.61 | -0.54 | 1 | 71.01 | 0.47 | N | 6 | CHEMBL97952 | CHEMBL97952 | CHEMBL97952 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Inhibition of human platelet aggregation induced by thrombin | CHEMBL1133830 | Non-molecular target assigned | N | null | 1 | CHEMBL372 | null | null | null | Homo sapiens | Homo sapiens | false | ORGANISM | 9,606 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Several benzimidazole derivatives have been identified as potent thrombin receptor (PAR-1) antagonists as represented by compound 1h, which showed an IC(50) of 33 nM. | Chackalamannil S, Doller D, Eagen K, Czarniecki M, Ahn HS, Foster CJ, Boykow G. | 10.1016/s0960-894x(01)00555-8 | null | 2851 | 21 | Bioorg Med Chem Lett | null | 11,597,414 | 1 | Potent, low molecular weight thrombin receptor antagonists. | 11 | 2,001 |
null | 40,624 | CHEMBL737009 | Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL90025 | null | null | 0 | null | 164,080 | = | 1 | 0 | = | Cholesterol | mM l-1 | 2.3 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Cholesterol | mM l-1 | null | 2.3 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 |
RDKit 2D
19 20 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 2 1 0
4 3 1 0
5 1 1 0
6 1 2 0
7 4 2 0
8 5 1 0
9 4 1 0
10 14 2 0
11 10 1 0
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13 8 2 0
14 13 1 0
15 12 2 0
16 2 2 0
17 3 2 0
18 19 2 0
19 16 1 0
10 15 1 0
18 17 1 0
M END
> <chembl_id>
CHEMBL90025
> <chembl_pref_name>
None | InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19) | WJSPLHRLEZJTRR-UHFFFAOYSA-N | 3.29 | 2 | C14H10ClNO3 | 275.69 | 2 | 2 | 19 | 275.69 | -1.26 | 0 | 66.4 | 0.9 | N | 3 | CHEMBL90025 | CHEMBL90025 | CHEMBL90025 | null | null | null | null | Mus musculus | null | null | 10,090 | Plasma | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | CHEMBL3559721 | null | null | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,626 | CHEMBL745439 | Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL90025 | null | null | 0 | null | 164,080 | = | 1 | 0 | = | Triglycerides | mM l-1 | 0.86 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Triglycerides | mM l-1 | null | 0.8600000000000001 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 |
RDKit 2D
19 20 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
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4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 2 1 0
4 3 1 0
5 1 1 0
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8 5 1 0
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14 13 1 0
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16 2 2 0
17 3 2 0
18 19 2 0
19 16 1 0
10 15 1 0
18 17 1 0
M END
> <chembl_id>
CHEMBL90025
> <chembl_pref_name>
None | InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19) | WJSPLHRLEZJTRR-UHFFFAOYSA-N | 3.29 | 2 | C14H10ClNO3 | 275.69 | 2 | 2 | 19 | 275.69 | -1.26 | 0 | 66.4 | 0.9 | N | 3 | CHEMBL90025 | CHEMBL90025 | CHEMBL90025 | null | null | null | null | Mus musculus | null | null | 10,090 | Plasma | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | CHEMBL3559721 | null | null | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,628 | CHEMBL733793 | Animal body weight was evaluated in Swiss white mice before treatment with the compound | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL90025 | null | null | 0 | http://qudt.org/vocab/unit#Gram | 164,080 | = | 1 | 0 | = | Body weight | g | 25 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Body weight | g | UO_0000021 | 25.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 |
RDKit 2D
19 20 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 2 1 0
4 3 1 0
5 1 1 0
6 1 2 0
7 4 2 0
8 5 1 0
9 4 1 0
10 14 2 0
11 10 1 0
12 8 1 0
13 8 2 0
14 13 1 0
15 12 2 0
16 2 2 0
17 3 2 0
18 19 2 0
19 16 1 0
10 15 1 0
18 17 1 0
M END
> <chembl_id>
CHEMBL90025
> <chembl_pref_name>
None | InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19) | WJSPLHRLEZJTRR-UHFFFAOYSA-N | 3.29 | 2 | C14H10ClNO3 | 275.69 | 2 | 2 | 19 | 275.69 | -1.26 | 0 | 66.4 | 0.9 | N | 3 | CHEMBL90025 | CHEMBL90025 | CHEMBL90025 | null | null | null | null | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Animal body weight was evaluated in Swiss white mice before treatment with the compound | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | null | null | null | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,629 | CHEMBL733794 | Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL90025 | null | null | 0 | http://qudt.org/vocab/unit#Gram | 164,080 | = | 1 | 0 | = | Body weight | g | 28 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Body weight | g | UO_0000021 | 28.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nc1ccc(Cl)cc1 |
RDKit 2D
19 20 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.4125 -0.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2042 -0.1875 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
4.9792 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7042 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4167 -1.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6917 0.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 2 1 0
4 3 1 0
5 1 1 0
6 1 2 0
7 4 2 0
8 5 1 0
9 4 1 0
10 14 2 0
11 10 1 0
12 8 1 0
13 8 2 0
14 13 1 0
15 12 2 0
16 2 2 0
17 3 2 0
18 19 2 0
19 16 1 0
10 15 1 0
18 17 1 0
M END
> <chembl_id>
CHEMBL90025
> <chembl_pref_name>
None | InChI=1S/C14H10ClNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19) | WJSPLHRLEZJTRR-UHFFFAOYSA-N | 3.29 | 2 | C14H10ClNO3 | 275.69 | 2 | 2 | 19 | 275.69 | -1.26 | 0 | 66.4 | 0.9 | N | 3 | CHEMBL90025 | CHEMBL90025 | CHEMBL90025 | null | null | null | null | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | null | null | ROUTE=None None | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,630 | CHEMBL737009 | Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nn1cnnc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL262903 | null | null | 0 | null | 164,077 | = | 1 | 0 | = | Cholesterol | mM l-1 | 2.46 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Cholesterol | mM l-1 | null | 2.46 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nn1cnnc1 |
RDKit 2D
17 18 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 6 1 0
3 8 2 0
4 9 2 0
5 1 1 0
6 1 1 0
7 5 1 0
8 2 1 0
9 2 1 0
10 7 1 0
11 1 2 0
12 10 2 0
13 10 1 0
14 5 2 0
15 7 2 0
16 17 2 0
17 14 1 0
4 3 1 0
15 16 1 0
M END
> <chembl_id>
CHEMBL262903
> <chembl_pref_name>
None | InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17) | JXXNYVAHSXIBNI-UHFFFAOYSA-N | 0.36 | 2 | C10H8N4O3 | 232.20 | 5 | 2 | 17 | 232.2 | -1.14 | 0 | 97.11 | 0.8 | N | 3 | CHEMBL262903 | CHEMBL262903 | CHEMBL262903 | null | null | null | null | Mus musculus | null | null | 10,090 | Plasma | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Plasma cholesterol level was evaluated in Swiss white mice before treatment with the compound | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | CHEMBL3559721 | null | null | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,631 | CHEMBL737010 | Plasma cholesterol level was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nn1cnnc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL262903 | null | null | 0 | null | 164,077 | = | 1 | 0 | = | Cholesterol | mM l-1 | 2.95 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Cholesterol | mM l-1 | null | 2.95 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nn1cnnc1 |
RDKit 2D
17 18 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 6 1 0
3 8 2 0
4 9 2 0
5 1 1 0
6 1 1 0
7 5 1 0
8 2 1 0
9 2 1 0
10 7 1 0
11 1 2 0
12 10 2 0
13 10 1 0
14 5 2 0
15 7 2 0
16 17 2 0
17 14 1 0
4 3 1 0
15 16 1 0
M END
> <chembl_id>
CHEMBL262903
> <chembl_pref_name>
None | InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17) | JXXNYVAHSXIBNI-UHFFFAOYSA-N | 0.36 | 2 | C10H8N4O3 | 232.20 | 5 | 2 | 17 | 232.2 | -1.14 | 0 | 97.11 | 0.8 | N | 3 | CHEMBL262903 | CHEMBL262903 | CHEMBL262903 | null | null | null | null | Mus musculus | null | null | 10,090 | Plasma | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Plasma cholesterol level was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | CHEMBL3559721 | null | ROUTE=None None | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,632 | CHEMBL745439 | Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nn1cnnc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL262903 | null | null | 0 | null | 164,077 | = | 1 | 0 | = | Triglycerides | mM l-1 | 1.12 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Triglycerides | mM l-1 | null | 1.12 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nn1cnnc1 |
RDKit 2D
17 18 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 6 1 0
3 8 2 0
4 9 2 0
5 1 1 0
6 1 1 0
7 5 1 0
8 2 1 0
9 2 1 0
10 7 1 0
11 1 2 0
12 10 2 0
13 10 1 0
14 5 2 0
15 7 2 0
16 17 2 0
17 14 1 0
4 3 1 0
15 16 1 0
M END
> <chembl_id>
CHEMBL262903
> <chembl_pref_name>
None | InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17) | JXXNYVAHSXIBNI-UHFFFAOYSA-N | 0.36 | 2 | C10H8N4O3 | 232.20 | 5 | 2 | 17 | 232.2 | -1.14 | 0 | 97.11 | 0.8 | N | 3 | CHEMBL262903 | CHEMBL262903 | CHEMBL262903 | null | null | null | null | Mus musculus | null | null | 10,090 | Plasma | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Plasma triglyceride level was evaluated in Swiss white mice before treatment with the compound | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | CHEMBL3559721 | null | null | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,634 | CHEMBL733793 | Animal body weight was evaluated in Swiss white mice before treatment with the compound | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nn1cnnc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL262903 | null | null | 0 | http://qudt.org/vocab/unit#Gram | 164,077 | = | 1 | 0 | = | Body weight | g | 35 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Body weight | g | UO_0000021 | 35.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nn1cnnc1 |
RDKit 2D
17 18 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 6 1 0
3 8 2 0
4 9 2 0
5 1 1 0
6 1 1 0
7 5 1 0
8 2 1 0
9 2 1 0
10 7 1 0
11 1 2 0
12 10 2 0
13 10 1 0
14 5 2 0
15 7 2 0
16 17 2 0
17 14 1 0
4 3 1 0
15 16 1 0
M END
> <chembl_id>
CHEMBL262903
> <chembl_pref_name>
None | InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17) | JXXNYVAHSXIBNI-UHFFFAOYSA-N | 0.36 | 2 | C10H8N4O3 | 232.20 | 5 | 2 | 17 | 232.2 | -1.14 | 0 | 97.11 | 0.8 | N | 3 | CHEMBL262903 | CHEMBL262903 | CHEMBL262903 | null | null | null | null | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Animal body weight was evaluated in Swiss white mice before treatment with the compound | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | null | null | null | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 40,635 | CHEMBL733794 | Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days | F | BAO_0000218 | organism-based format | O=C(O)c1ccccc1C(=O)Nn1cnnc1 | null | CHEMBL1133800 | Bioorg Med Chem Lett | 2,001 | CHEMBL262903 | null | null | 0 | http://qudt.org/vocab/unit#Gram | 164,077 | = | 1 | 0 | = | Body weight | g | 39 | CHEMBL375 | Mus musculus | Mus musculus | 10090 | null | Body weight | g | UO_0000021 | 39.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)c1ccccc1C(=O)Nn1cnnc1 |
RDKit 2D
17 18 0 0 0 0 0 0 0 0999 V2000
4.2875 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9917 -1.2375 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.2917 -0.9500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.8750 -0.2417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2792 -1.6542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5750 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7417 -1.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0667 -0.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1542 -4.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0792 -2.6917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -5.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -4.1000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -2.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8542 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -3.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -2.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 6 1 0
3 8 2 0
4 9 2 0
5 1 1 0
6 1 1 0
7 5 1 0
8 2 1 0
9 2 1 0
10 7 1 0
11 1 2 0
12 10 2 0
13 10 1 0
14 5 2 0
15 7 2 0
16 17 2 0
17 14 1 0
4 3 1 0
15 16 1 0
M END
> <chembl_id>
CHEMBL262903
> <chembl_pref_name>
None | InChI=1S/C10H8N4O3/c15-9(13-14-5-11-12-6-14)7-3-1-2-4-8(7)10(16)17/h1-6H,(H,13,15)(H,16,17) | JXXNYVAHSXIBNI-UHFFFAOYSA-N | 0.36 | 2 | C10H8N4O3 | 232.20 | 5 | 2 | 17 | 232.2 | -1.14 | 0 | 97.11 | 0.8 | N | 3 | CHEMBL262903 | CHEMBL262903 | CHEMBL262903 | null | null | null | null | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Animal body weight was evaluated in Swiss white mice treated with 20 mg/kg/day of ip administration for 14 days | CHEMBL1133800 | Non-molecular target assigned | N | null | 1 | CHEMBL375 | null | null | ROUTE=None None | Mus musculus | Mus musculus | false | ORGANISM | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight. | Sena VL, Srivastava RM, Oliveira SP, Lima VL. | 10.1016/s0960-894x(01)00540-6 | null | 2671 | 20 | Bioorg Med Chem Lett | null | 11,591,498 | 1 | Microwave assisted synthesis of N-arylphthalamic acids with hyperlipidemic activity. | 11 | 2,001 |
null | 34,377 | CHEMBL636019 | True partition coefficient corrected for ionization was determined | P | BAO_0000100 | small-molecule physicochemical format | CN(C)CCc1c[nH]c2cccc(O)c12 | null | CHEMBL1121785 | J Med Chem | 1,981 | CHEMBL65547 | PSILOCIN | null | 0 | null | 113,388 | = | 1 | 0 | = | pKa | null | 42.1 | CHEMBL2362975 | null | No relevant target | null | null | pKa | null | null | 42.1 | null | null | null | null | null | 0 | 2 | null | null | 0 | 2.0 | Small molecule | 1 | false | false | 0 | PSILOCIN | 0 | MOL | false | false | deu- | null | false | CN(C)CCc1c[nH]c2cccc(O)c12 |
RDKit 2D
15 16 0 0 0 0 0 0 0 0999 V2000
3.0857 -19.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0845 -20.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7992 -20.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7974 -19.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3025 -20.7133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.7903 -20.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3020 -19.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5127 -19.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5130 -20.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.5567 -18.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.3635 -18.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.6180 -17.6293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.4248 -17.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0659 -17.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7950 -18.3931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
8 4 2 0
5 6 1 0
7 8 1 0
9 5 1 0
4 1 1 0
7 10 1 0
8 9 1 0
10 11 1 0
11 12 1 0
2 3 1 0
12 13 1 0
6 7 2 0
12 14 1 0
3 9 2 0
4 15 1 0
M END
> <chembl_id>
CHEMBL65547
> <chembl_pref_name>
PSILOCIN | InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3 | SPCIYGNTAMCTRO-UHFFFAOYSA-N | 1.98 | 2 | C12H16N2O | 204.27 | 2 | 2 | 15 | 204.27 | 0.31 | 0 | 39.26 | 0.8 | Y | 3 | CHEMBL65547 | CHEMBL65547 | CHEMBL65547 | 4-ho-dmt [OTHER] | Psilocin [OTHER] | Psilocyn [OTHER] | null | null | null | null | null | null | null | null | P | Physicochemical | BAO_0000100 | small-molecule physicochemical format | null | Default value - Target unknown or has yet to be assigned | 0 | True partition coefficient corrected for ionization was determined | CHEMBL1121785 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL2362975 | null | null | null | null | No relevant target | false | NO TARGET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The 360-MHz 1H NMR spectra of bufotenin and psilocin were obtained, both as the free bases in CDCl3 and as protonated salts in D2O. Coupling constants for the side-chain methylenes were derived using the LAOCN3 program. These time-averaged coupling constants indicate that the trans and gauche rotamers of both compounds have about equal energy in D2O. There is a slight excess of the trans rotamer of bufotenin in CDCl3. For psilocin, in contrast, the gauche form is highly favored in CDCl3. The magnitude of this stabilization was estimated at about 1 kcal/mol using rotamer populations and free energy of transfer from published partitioning studies. It is suggested that this could result from a very weak hydrogen bond. On the other hand, the difference in partitioning between bufotenin and psilocin, which seems to be a major determinant of biological activity, is largely due to a difference in the basicity of the two compounds. The pKa values for the amino group of psilocin and bufotenin were determined to be 8.47 and 9.67, respectively. | Migliaccio GP, Shieh TL, Byrn SR, Hathaway BA, Nichols DE. | 10.1021/jm00134a016 | null | 206 | 2 | J Med Chem | null | 6,259,355 | 1 | Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy. | 24 | 1,981 |
null | 34,378 | CHEMBL638404 | Partition coefficient of octanol and water was determined | P | BAO_0000100 | small-molecule physicochemical format | CN(C)CCc1c[nH]c2cccc(O)c12 | null | CHEMBL1121785 | J Med Chem | 1,981 | CHEMBL65547 | PSILOCIN | null | 0 | null | 113,388 | = | 1 | 0 | = | Poct | null | 0.68 | CHEMBL2362975 | null | No relevant target | null | null | Poct | null | null | 0.68 | null | null | null | null | null | 0 | 2 | null | null | 0 | 2.0 | Small molecule | 1 | false | false | 0 | PSILOCIN | 0 | MOL | false | false | deu- | null | false | CN(C)CCc1c[nH]c2cccc(O)c12 |
RDKit 2D
15 16 0 0 0 0 0 0 0 0999 V2000
3.0857 -19.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0845 -20.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7992 -20.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7974 -19.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3025 -20.7133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.7903 -20.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3020 -19.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5127 -19.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5130 -20.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.5567 -18.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.3635 -18.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.6180 -17.6293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.4248 -17.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0659 -17.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7950 -18.3931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
8 4 2 0
5 6 1 0
7 8 1 0
9 5 1 0
4 1 1 0
7 10 1 0
8 9 1 0
10 11 1 0
11 12 1 0
2 3 1 0
12 13 1 0
6 7 2 0
12 14 1 0
3 9 2 0
4 15 1 0
M END
> <chembl_id>
CHEMBL65547
> <chembl_pref_name>
PSILOCIN | InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3 | SPCIYGNTAMCTRO-UHFFFAOYSA-N | 1.98 | 2 | C12H16N2O | 204.27 | 2 | 2 | 15 | 204.27 | 0.31 | 0 | 39.26 | 0.8 | Y | 3 | CHEMBL65547 | CHEMBL65547 | CHEMBL65547 | 4-ho-dmt [OTHER] | Psilocin [OTHER] | Psilocyn [OTHER] | null | null | null | null | null | null | null | null | P | Physicochemical | BAO_0000100 | small-molecule physicochemical format | null | Default value - Target unknown or has yet to be assigned | 0 | Partition coefficient of octanol and water was determined | CHEMBL1121785 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL2362975 | null | null | null | null | No relevant target | false | NO TARGET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The 360-MHz 1H NMR spectra of bufotenin and psilocin were obtained, both as the free bases in CDCl3 and as protonated salts in D2O. Coupling constants for the side-chain methylenes were derived using the LAOCN3 program. These time-averaged coupling constants indicate that the trans and gauche rotamers of both compounds have about equal energy in D2O. There is a slight excess of the trans rotamer of bufotenin in CDCl3. For psilocin, in contrast, the gauche form is highly favored in CDCl3. The magnitude of this stabilization was estimated at about 1 kcal/mol using rotamer populations and free energy of transfer from published partitioning studies. It is suggested that this could result from a very weak hydrogen bond. On the other hand, the difference in partitioning between bufotenin and psilocin, which seems to be a major determinant of biological activity, is largely due to a difference in the basicity of the two compounds. The pKa values for the amino group of psilocin and bufotenin were determined to be 8.47 and 9.67, respectively. | Migliaccio GP, Shieh TL, Byrn SR, Hathaway BA, Nichols DE. | 10.1021/jm00134a016 | null | 206 | 2 | J Med Chem | null | 6,259,355 | 1 | Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy. | 24 | 1,981 |
null | 34,379 | CHEMBL637888 | Partition coefficient (logP) | P | BAO_0000100 | small-molecule physicochemical format | CN(C)CCc1c[nH]c2cccc(O)c12 | null | CHEMBL1121785 | J Med Chem | 1,981 | CHEMBL65547 | PSILOCIN | null | 0 | null | 113,388 | = | 1 | 1 | = | LogP | null | 1.45 | CHEMBL2362975 | null | No relevant target | null | null | logP | null | null | 1.45 | null | null | null | null | null | 0 | 2 | null | null | 0 | 2.0 | Small molecule | 1 | false | false | 0 | PSILOCIN | 0 | MOL | false | false | deu- | null | false | CN(C)CCc1c[nH]c2cccc(O)c12 |
RDKit 2D
15 16 0 0 0 0 0 0 0 0999 V2000
3.0857 -19.6308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0845 -20.4581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7992 -20.8708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7974 -19.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3025 -20.7133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.7903 -20.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3020 -19.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5127 -19.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5130 -20.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.5567 -18.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.3635 -18.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.6180 -17.6293 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.4248 -17.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0659 -17.0165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7950 -18.3931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
8 4 2 0
5 6 1 0
7 8 1 0
9 5 1 0
4 1 1 0
7 10 1 0
8 9 1 0
10 11 1 0
11 12 1 0
2 3 1 0
12 13 1 0
6 7 2 0
12 14 1 0
3 9 2 0
4 15 1 0
M END
> <chembl_id>
CHEMBL65547
> <chembl_pref_name>
PSILOCIN | InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3 | SPCIYGNTAMCTRO-UHFFFAOYSA-N | 1.98 | 2 | C12H16N2O | 204.27 | 2 | 2 | 15 | 204.27 | 0.31 | 0 | 39.26 | 0.8 | Y | 3 | CHEMBL65547 | CHEMBL65547 | CHEMBL65547 | 4-ho-dmt [OTHER] | Psilocin [OTHER] | Psilocyn [OTHER] | null | null | null | null | null | null | null | null | P | Physicochemical | BAO_0000100 | small-molecule physicochemical format | null | Default value - Target unknown or has yet to be assigned | 0 | Partition coefficient (logP) | CHEMBL1121785 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL2362975 | null | null | null | null | No relevant target | false | NO TARGET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The 360-MHz 1H NMR spectra of bufotenin and psilocin were obtained, both as the free bases in CDCl3 and as protonated salts in D2O. Coupling constants for the side-chain methylenes were derived using the LAOCN3 program. These time-averaged coupling constants indicate that the trans and gauche rotamers of both compounds have about equal energy in D2O. There is a slight excess of the trans rotamer of bufotenin in CDCl3. For psilocin, in contrast, the gauche form is highly favored in CDCl3. The magnitude of this stabilization was estimated at about 1 kcal/mol using rotamer populations and free energy of transfer from published partitioning studies. It is suggested that this could result from a very weak hydrogen bond. On the other hand, the difference in partitioning between bufotenin and psilocin, which seems to be a major determinant of biological activity, is largely due to a difference in the basicity of the two compounds. The pKa values for the amino group of psilocin and bufotenin were determined to be 8.47 and 9.67, respectively. | Migliaccio GP, Shieh TL, Byrn SR, Hathaway BA, Nichols DE. | 10.1021/jm00134a016 | null | 206 | 2 | J Med Chem | null | 6,259,355 | 1 | Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy. | 24 | 1,981 |
null | 34,380 | CHEMBL668662 | Inhibition of dihydrofolate reductase from bovine liver | B | BAO_0000019 | assay format | CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1 | null | CHEMBL1121828 | J Med Chem | 1,981 | CHEMBL31235 | null | null | 0 | null | 295,584 | = | 1 | 0 | = | Log 1/Ki app | null | 5.78 | CHEMBL1075051 | Bos taurus | Dihydrofolate reductase | 9913 | null | Log 1/Ki app | null | null | 5.78 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1 |
RDKit 2D
24 25 0 0 0 0 0 0 0 0999 V2000
0.7417 -4.2792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.2542 -3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7792 -4.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7417 -4.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2542 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.7792 -4.8792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2917 -3.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8167 -4.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2500 -3.3792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.2167 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.8167 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -5.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -5.7750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.8667 -4.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -3.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8667 -4.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8167 -6.0667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8125 -6.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2292 -8.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7542 -8.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7625 -7.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2917 -6.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2792 -7.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2250 -9.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 2 1 0
4 1 1 0
5 4 2 0
6 5 1 0
7 3 1 0
8 7 1 0
9 2 1 0
10 4 1 0
11 8 2 0
12 11 1 0
13 12 1 0
14 15 2 0
15 8 1 0
16 14 1 0
17 13 1 0
18 17 1 0
19 20 1 0
20 21 1 0
21 23 1 0
22 18 1 0
23 22 1 0
24 19 1 0
6 3 2 0
16 12 2 0
M END
> <chembl_id>
CHEMBL31235
> <chembl_pref_name>
None | InChI=1S/C19H28N4O/c1-2-3-4-5-6-7-11-24-17-10-8-9-15(13-17)12-16-14-22-19(21)23-18(16)20/h8-10,13-14H,2-7,11-12H2,1H3,(H4,20,21,22,23) | RNZGHILIUCETNY-UHFFFAOYSA-N | 3.97 | 2 | C19H28N4O | 328.46 | 5 | 2 | 24 | 328.46 | -0.34 | 0 | 87.05 | 0.64 | N | 10 | CHEMBL31235 | CHEMBL31235 | CHEMBL31235 | null | null | null | null | Bos taurus | null | null | 9,913 | null | B | Binding | BAO_0000019 | assay format | null | Direct single protein target assigned | 9 | Inhibition of dihydrofolate reductase from bovine liver | CHEMBL1121828 | Direct protein target assigned | D | null | 1 | CHEMBL1075051 | null | null | null | Bos taurus | Dihydrofolate reductase | false | SINGLE PROTEIN | 9,913 | P00376 | Dihydrofolate reductase | PROTEIN | 4,114 | 1 | null | null | null | null | null | null | null | null | null | null | null | In our previous publication (Blaney, J. M.; Dietrich, S. W.; Reynolds, M. A.; Hansch, C. J. Med. Chem. 1979, 22, 614), correlation equations were presented for the inhibition of bovine liver and Escherichia coli dihydrofolate reductase (DHFR) by 5-(substituted benzyl)-2,4-diaminopyrimidines. These equations brought out differences in the way these two enzymes interact with substituents, which explain the high selectivity of drugs like trimethoprim. We have tested and further developed these equations in this report. It is of particular interest that our previously published correlation equation for E. coli DHFR accurately predicted the potency of a commercial competitor of trimethoprim (tetroxoprim) now in clinical use. We believe that new and effective competitors for trimethoprim can be designed by means of the two correlation equations. | Li RL, Dietrich SW, Hansch C. | 10.1021/jm00137a012 | null | 538 | 5 | J Med Chem | null | 7,017,146 | 1 | Quantitative structure-selectivity relationships. Comparison of the inhibition of Escherichia coli and bovine liver dihydrofolate reductase by 5-(substituted-benzyl)-2,4-diaminopyrimidines. | 24 | 1,981 |
null | 34,381 | CHEMBL668773 | Compound is evaluated for the inhibition of dihydrofolate reductase from Escherichia coli | B | BAO_0000357 | single protein format | CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1 | null | CHEMBL1121828 | J Med Chem | 1,981 | CHEMBL31235 | null | null | 0 | null | 295,584 | = | 1 | 0 | = | Log 1/Ki app | null | 6.25 | CHEMBL1809 | Escherichia coli | Dihydrofolate reductase | 562 | null | Log 1/Ki app | null | null | 6.25 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCCCCOc1cccc(Cc2cnc(N)nc2N)c1 |
RDKit 2D
24 25 0 0 0 0 0 0 0 0999 V2000
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1.2542 -3.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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0.2167 -5.1792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.8167 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -5.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3417 -5.7750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.8667 -4.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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3.8667 -4.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8167 -6.0667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8125 -6.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2292 -8.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7542 -8.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7625 -7.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2917 -6.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2792 -7.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.2250 -9.3250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 2 1 0
4 1 1 0
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6 5 1 0
7 3 1 0
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23 22 1 0
24 19 1 0
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16 12 2 0
M END
> <chembl_id>
CHEMBL31235
> <chembl_pref_name>
None | InChI=1S/C19H28N4O/c1-2-3-4-5-6-7-11-24-17-10-8-9-15(13-17)12-16-14-22-19(21)23-18(16)20/h8-10,13-14H,2-7,11-12H2,1H3,(H4,20,21,22,23) | RNZGHILIUCETNY-UHFFFAOYSA-N | 3.97 | 2 | C19H28N4O | 328.46 | 5 | 2 | 24 | 328.46 | -0.34 | 0 | 87.05 | 0.64 | N | 10 | CHEMBL31235 | CHEMBL31235 | CHEMBL31235 | null | null | null | null | Escherichia coli | null | null | 562 | null | B | Binding | BAO_0000357 | single protein format | null | Direct single protein target assigned | 9 | Compound is evaluated for the inhibition of dihydrofolate reductase from Escherichia coli | CHEMBL1121828 | Direct protein target assigned | D | null | 1 | CHEMBL1809 | null | null | null | Escherichia coli | Dihydrofolate reductase | false | SINGLE PROTEIN | 562 | P0ABQ4 | Dihydrofolate reductase | PROTEIN | 103 | 1 | null | null | null | null | null | null | null | null | null | null | null | In our previous publication (Blaney, J. M.; Dietrich, S. W.; Reynolds, M. A.; Hansch, C. J. Med. Chem. 1979, 22, 614), correlation equations were presented for the inhibition of bovine liver and Escherichia coli dihydrofolate reductase (DHFR) by 5-(substituted benzyl)-2,4-diaminopyrimidines. These equations brought out differences in the way these two enzymes interact with substituents, which explain the high selectivity of drugs like trimethoprim. We have tested and further developed these equations in this report. It is of particular interest that our previously published correlation equation for E. coli DHFR accurately predicted the potency of a commercial competitor of trimethoprim (tetroxoprim) now in clinical use. We believe that new and effective competitors for trimethoprim can be designed by means of the two correlation equations. | Li RL, Dietrich SW, Hansch C. | 10.1021/jm00137a012 | null | 538 | 5 | J Med Chem | null | 7,017,146 | 1 | Quantitative structure-selectivity relationships. Comparison of the inhibition of Escherichia coli and bovine liver dihydrofolate reductase by 5-(substituted-benzyl)-2,4-diaminopyrimidines. | 24 | 1,981 |
null | 34,382 | CHEMBL847678 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | F | BAO_0000019 | assay format | C[C@@H](Cc1ccco1)NC(=O)[C@H](N)CC(=O)O | null | CHEMBL1121833 | J Med Chem | 1,981 | CHEMBL154919 | null | null | 0 | null | 302,439 | = | 1 | 0 | = | Log SP | null | 1.16 | CHEMBL612545 | null | Unchecked | null | null | Log SP | null | null | 1.16 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | C[C@@H](Cc1ccco1)NC(=O)[C@H](N)CC(=O)O |
RDKit 2D
17 17 0 0 1 0 0 0 0 0999 V2000
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-3.0625 -0.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5083 -0.6875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.5458 -0.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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0.0542 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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1.0042 -1.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.5833 -0.0875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.9833 -0.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5458 -0.0875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-4.1000 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.9833 -1.5875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 4 1 0
3 1 1 0
4 1 1 0
5 2 1 0
6 8 1 0
7 6 1 0
8 14 1 0
9 1 2 0
10 6 2 0
11 7 1 0
12 10 1 0
13 5 2 0
14 3 1 0
4 15 1 1
16 5 1 0
14 17 1 6
12 11 2 0
M END
> <chembl_id>
CHEMBL154919
> <chembl_pref_name>
None | InChI=1S/C11H16N2O4/c1-7(5-8-3-2-4-17-8)13-11(16)9(12)6-10(14)15/h2-4,7,9H,5-6,12H2,1H3,(H,13,16)(H,14,15)/t7-,9+/m0/s1 | VOQPIRFCQUFIFQ-IONNQARKSA-N | 0.13 | 1 | C11H16N2O4 | 240.26 | 4 | 3 | 17 | 240.26 | -0.55 | 0 | 105.56 | 0.65 | N | 6 | CHEMBL154919 | CHEMBL154919 | CHEMBL154919 | null | null | null | null | null | null | null | null | null | F | Functional | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | CHEMBL1121833 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures. | Iwamura H. | 10.1021/jm00137a018 | null | 572 | 5 | J Med Chem | null | 7,241,515 | 1 | Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology. | 24 | 1,981 |
null | 34,383 | CHEMBL847678 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | F | BAO_0000019 | assay format | CC[C@@H](Cc1ccccc1)NC(=O)[C@H](N)CC(=O)O | null | CHEMBL1121833 | J Med Chem | 1,981 | CHEMBL345850 | null | null | 0 | null | 302,650 | = | 1 | 0 | = | Log SP | null | 0.89 | CHEMBL612545 | null | Unchecked | null | null | Log SP | null | null | 0.89 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CC[C@@H](Cc1ccccc1)NC(=O)[C@H](N)CC(=O)O |
RDKit 2D
19 19 0 0 1 0 0 0 0 0999 V2000
-1.5708 0.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.6083 0.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0500 0.5208 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.0958 0.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.1250 0.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-3.1250 1.1208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.5333 0.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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0.5042 0.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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0.5042 -0.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0167 0.5250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0458 -0.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5417 0.2333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0250 -0.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5417 -0.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 4 1 0
3 1 1 0
4 1 1 0
5 2 1 0
6 1 2 0
7 5 2 0
8 3 1 0
4 9 1 1
10 8 1 0
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12 10 1 0
8 13 1 6
14 12 2 0
15 12 1 0
16 13 1 0
17 15 2 0
18 14 1 0
19 17 1 0
19 18 2 0
M END
> <chembl_id>
CHEMBL345850
> <chembl_pref_name>
None | InChI=1S/C14H20N2O3/c1-2-11(8-10-6-4-3-5-7-10)16-14(19)12(15)9-13(17)18/h3-7,11-12H,2,8-9,15H2,1H3,(H,16,19)(H,17,18)/t11-,12+/m0/s1 | SIXSBZCTRDJENX-NWDGAFQWSA-N | 0.93 | 1 | C14H20N2O3 | 264.32 | 3 | 3 | 19 | 264.32 | 0.15 | 0 | 92.42 | 0.68 | N | 7 | CHEMBL345850 | CHEMBL345850 | CHEMBL345850 | null | null | null | null | null | null | null | null | null | F | Functional | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | CHEMBL1121833 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures. | Iwamura H. | 10.1021/jm00137a018 | null | 572 | 5 | J Med Chem | null | 7,241,515 | 1 | Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology. | 24 | 1,981 |
null | 34,386 | CHEMBL847678 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | F | BAO_0000019 | assay format | C[C@@H](COC(=O)C1CCCC1)NC(=O)[C@H](N)CC(=O)O | null | CHEMBL1121833 | J Med Chem | 1,981 | CHEMBL434078 | null | null | 0 | null | 302,608 | = | 1 | 0 | = | Log SP | null | 1.7 | CHEMBL612545 | null | Unchecked | null | null | Log SP | null | null | 1.7 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | C[C@@H](COC(=O)C1CCCC1)NC(=O)[C@H](N)CC(=O)O |
RDKit 2D
20 20 0 0 1 0 0 0 0 0999 V2000
-3.4458 -0.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.4833 -0.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.8458 -0.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.9250 -0.5667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-3.9708 -0.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-2.4083 -0.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.2625 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2167 -0.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4083 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6250 -1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3250 -1.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 5 1 0
3 7 1 0
4 1 1 0
5 1 1 0
6 2 1 0
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8 1 2 0
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10 6 2 0
11 3 1 0
5 12 1 1
13 6 1 0
14 15 1 0
15 4 1 0
16 11 1 0
17 11 1 0
15 18 1 6
19 17 1 0
20 16 1 0
19 20 1 0
M END
> <chembl_id>
CHEMBL434078
> <chembl_pref_name>
None | InChI=1S/C13H22N2O5/c1-8(15-12(18)10(14)6-11(16)17)7-20-13(19)9-4-2-3-5-9/h8-10H,2-7,14H2,1H3,(H,15,18)(H,16,17)/t8-,10+/m0/s1 | CUSAUPTWLADOAS-WCBMZHEXSA-N | 0.03 | 0 | C13H22N2O5 | 286.33 | 5 | 3 | 20 | 286.33 | -0.01 | 0 | 118.72 | 0.57 | N | 7 | CHEMBL434078 | CHEMBL434078 | CHEMBL434078 | null | null | null | null | null | null | null | null | null | F | Functional | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | CHEMBL1121833 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures. | Iwamura H. | 10.1021/jm00137a018 | null | 572 | 5 | J Med Chem | null | 7,241,515 | 1 | Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology. | 24 | 1,981 |
null | 34,387 | CHEMBL847678 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | F | BAO_0000019 | assay format | CC[C@H](NC(=O)[C@H](N)CC(=O)O)C(=O)OC | null | CHEMBL1121833 | J Med Chem | 1,981 | CHEMBL345229 | null | null | 0 | null | 302,539 | = | 1 | 0 | = | Log SP | null | 1.04 | CHEMBL612545 | null | Unchecked | null | null | Log SP | null | null | 1.04 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CC[C@H](NC(=O)[C@H](N)CC(=O)O)C(=O)OC |
RDKit 2D
16 15 0 0 1 0 0 0 0 0999 V2000
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0.7292 -1.0417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-3.4208 -1.0375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.3083 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7375 -1.6417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.8208 -1.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 5 1 0
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5 1 1 0
6 3 1 0
7 2 1 0
8 1 2 0
9 4 2 0
10 6 2 0
5 11 1 1
12 4 1 0
13 6 1 0
7 14 1 6
15 12 1 0
16 14 1 0
M END
> <chembl_id>
CHEMBL345229
> <chembl_pref_name>
None | InChI=1S/C9H16N2O5/c1-3-6(9(15)16-2)11-8(14)5(10)4-7(12)13/h5-6H,3-4,10H2,1-2H3,(H,11,14)(H,12,13)/t5-,6+/m1/s1 | OEHNLOQCFKDMNG-RITPCOANSA-N | -1.14 | 0 | C9H16N2O5 | 232.24 | 5 | 3 | 16 | 232.24 | 0.44 | 0 | 118.72 | 0.5 | N | 6 | CHEMBL345229 | CHEMBL345229 | CHEMBL345229 | null | null | null | null | null | null | null | null | null | F | Functional | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | CHEMBL1121833 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures. | Iwamura H. | 10.1021/jm00137a018 | null | 572 | 5 | J Med Chem | null | 7,241,515 | 1 | Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology. | 24 | 1,981 |
null | 34,388 | CHEMBL847678 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | F | BAO_0000019 | assay format | CC(Cc1ccccc1)NC(=O)[C@H](N)CC(=O)O | null | CHEMBL1121833 | J Med Chem | 1,981 | CHEMBL153822 | null | null | 0 | null | 302,489 | = | 1 | 0 | = | Log SP | null | 1.56 | CHEMBL612545 | null | Unchecked | null | null | Log SP | null | null | 1.56 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CC(Cc1ccccc1)NC(=O)[C@H](N)CC(=O)O |
RDKit 2D
18 18 0 0 1 0 0 0 0 0999 V2000
-1.2708 -0.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.3083 -0.6125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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1.3250 -0.3042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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1.8417 -0.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2 4 1 0
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M END
> <chembl_id>
CHEMBL153822
> <chembl_pref_name>
None | InChI=1S/C13H18N2O3/c1-9(7-10-5-3-2-4-6-10)15-13(18)11(14)8-12(16)17/h2-6,9,11H,7-8,14H2,1H3,(H,15,18)(H,16,17)/t9?,11-/m1/s1 | DADLXGFKJVGHGU-HCCKASOXSA-N | 0.54 | 1 | C13H18N2O3 | 250.30 | 3 | 3 | 18 | 250.3 | -0.14 | 0 | 92.42 | 0.69 | N | 6 | CHEMBL153822 | CHEMBL153822 | CHEMBL153822 | null | null | null | null | null | null | null | null | null | F | Functional | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | CHEMBL1121833 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures. | Iwamura H. | 10.1021/jm00137a018 | null | 572 | 5 | J Med Chem | null | 7,241,515 | 1 | Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology. | 24 | 1,981 |
null | 34,389 | CHEMBL847678 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | F | BAO_0000019 | assay format | CCCCCC[C@H](C)NC(=O)[C@H](N)CC(=O)O | null | CHEMBL1121833 | J Med Chem | 1,981 | CHEMBL154383 | null | null | 0 | null | 302,485 | = | 1 | 0 | = | Log SP | null | 1.58 | CHEMBL612545 | null | Unchecked | null | null | Log SP | null | null | 1.58 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCC[C@H](C)NC(=O)[C@H](N)CC(=O)O |
RDKit 2D
17 16 0 0 1 0 0 0 0 0999 V2000
-3.5375 -0.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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0.1000 0.1125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4208 -0.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2 4 1 0
3 1 1 0
4 1 1 0
5 2 1 0
6 1 2 0
7 5 2 0
4 8 1 1
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10 3 1 0
11 10 1 0
10 12 1 6
13 14 1 0
14 16 1 0
15 11 1 0
16 15 1 0
17 13 1 0
M END
> <chembl_id>
CHEMBL154383
> <chembl_pref_name>
None | InChI=1S/C12H24N2O3/c1-3-4-5-6-7-9(2)14-12(17)10(13)8-11(15)16/h9-10H,3-8,13H2,1-2H3,(H,14,17)(H,15,16)/t9-,10+/m0/s1 | KCYZZFRWSADIIG-VHSXEESVSA-N | 1.26 | 0 | C12H24N2O3 | 244.33 | 3 | 3 | 17 | 244.33 | 0.33 | 0 | 92.42 | 0.53 | N | 9 | CHEMBL154383 | CHEMBL154383 | CHEMBL154383 | null | null | null | null | null | null | null | null | null | F | Functional | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Sweet potency as logarithm of sweet potency (log SP) relative to sucrose | CHEMBL1121833 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The relationship between structure and the sweet potency of L-aspartyl dipeptide analogues was investigated by physicochemical parameters and regression analysis. The dipeptide analogues reported were divided into the following four classes: L-aspartic acid amides, L-aspartylaminoethyl esters, L-aspartylaminopropionates, and L-aspartyl-aminoacetates. The analysis carried out for each class indicated that the electron-withdrawing effect of the substituents directed to the peptide bond and the steric dimensions of the molecules are important in eliciting the sweet taste. The values of coefficients of the electronic sigma terms in the correlations for L-aspartic acid amides, L-aspartylaminoethyl esters, and L-aspartylaminopropionates were approximately 0.7, indicating a common basic site on the receptor surface. The value for L-aspartylaminoacetates was approximately 1.5, and this value suggests, together with the factor of the participation of steric parameters, a closer or geometrically more proper fit to the receptor, explaining the generally higher potency of this class compared to the other three. The receptor model drawn based on these quantitative analyses appears to be consistent with other classes of sweeteners of apparently unrelated structures. | Iwamura H. | 10.1021/jm00137a018 | null | 572 | 5 | J Med Chem | null | 7,241,515 | 1 | Structure--sweetness relationship of L-aspartyl dipeptide analogues. A receptor site topology. | 24 | 1,981 |
null | 34,392 | CHEMBL784534 | Antiallergic activity was evaluated by passive cutaneous anaphylaxis test in egg albumin sensitized male Harlan-Sprague-Dawley rats when administered perorally | F | BAO_0000218 | organism-based format | O=C1c2[nH]nnc2N(Cc2ccc(F)cc2)C2=NCCN12 | null | CHEMBL1121553 | J Med Chem | 1,980 | CHEMBL18489 | null | null | 0 | null | 22,459 | = | 1 | 1 | = | ED50 | mg.kg-1 | 17.7 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | ED50 | mg kg-1 | UO_0000308 | 17.7 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C1c2[nH]nnc2N(Cc2ccc(F)cc2)C2=NCCN12 |
RDKit 2D
21 24 0 0 0 0 0 0 0 0999 V2000
4.5792 -3.9792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.8667 -3.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3042 -3.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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4.5792 -2.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.5875 -3.1542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
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6.0917 -3.8167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.5792 -4.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5875 -1.4917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
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2 1 1 0
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13 14 1 0
6 5 1 0
8 9 1 0
16 21 1 0
M END
> <chembl_id>
CHEMBL18489
> <chembl_pref_name>
None | InChI=1S/C13H11FN6O/c14-9-3-1-8(2-4-9)7-20-11-10(16-18-17-11)12(21)19-6-5-15-13(19)20/h1-4H,5-7H2,(H,16,17,18) | PZBVSAQNUMAWOE-UHFFFAOYSA-N | 0.78 | 2 | C13H11FN6O | 286.27 | 5 | 1 | 21 | 286.27 | -1.55 | 0 | 77.48 | 0.88 | N | 2 | CHEMBL18489 | CHEMBL18489 | CHEMBL18489 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Antiallergic activity was evaluated by passive cutaneous anaphylaxis test in egg albumin sensitized male Harlan-Sprague-Dawley rats when administered perorally | CHEMBL1121553 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat. | Temple DL, Yevich JP, Catt JD, Owens D, Hanning C, Covington RR, Seidehamel RJ, Dungan KW. | 10.1021/jm00185a008 | null | 1188 | 11 | J Med Chem | null | 6,161,252 | 1 | Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones. | 23 | 1,980 |
null | 34,393 | CHEMBL773605 | Lowest active dose which cured rats with Entamoeba histolytica cecal infection was measured | F | BAO_0000218 | organism-based format | CCCN1CCN(c2nc3ccc(/N=C/N(C)C)cc3nc2N2CCN(CCC)CC2)CC1 | null | CHEMBL1121391 | J Med Chem | 1,980 | CHEMBL66079 | null | null | 0 | null | 110,555 | = | 1 | 0 | = | Dose | mg kg-1 day-1 | 50 | CHEMBL612853 | Entamoeba histolytica | Entamoeba histolytica | 5759 | null | Dose | mg kg-1 day-1 | UO_0000311 | 50.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCN1CCN(c2nc3ccc(/N=C/N(C)C)cc3nc2N2CCN(CCC)CC2)CC1 |
RDKit 2D
33 36 0 0 0 0 0 0 0 0999 V2000
5.7000 -6.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6917 -5.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9875 -6.6292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.9792 -4.9750 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4042 -4.9667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4167 -6.6167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.2667 -6.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2667 -5.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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1.4125 -6.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.8292 -4.1292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.8417 -7.4417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -6.6292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.1167 -5.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.1250 -6.2000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4000 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.8417 -6.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.8417 -5.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.5542 -7.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.5417 -3.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0208 -6.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6917 -7.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.2542 -4.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.2667 -7.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.9750 -3.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.9875 -7.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
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24 12 1 0
4 8 1 0
23 11 1 0
20 25 1 0
M END
> <chembl_id>
CHEMBL66079
> <chembl_pref_name>
None | InChI=1S/C25H40N8/c1-5-9-30-11-15-32(16-12-30)24-25(33-17-13-31(10-6-2)14-18-33)28-23-19-21(26-20-29(3)4)7-8-22(23)27-24/h7-8,19-20H,5-6,9-18H2,1-4H3/b26-20+ | PYQRPNZZTJLWTE-LHLOQNFPSA-N | 2.92 | 2 | C25H40N8 | 452.65 | 7 | 0 | 33 | 452.65 | -1.17 | 0 | 54.34 | 0.45 | N | 8 | CHEMBL66079 | CHEMBL66079 | CHEMBL66079 | null | null | null | null | Entamoeba histolytica | null | null | 5,759 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Lowest active dose which cured rats with Entamoeba histolytica cecal infection was measured | CHEMBL1121391 | Non-molecular target assigned | N | null | 1 | CHEMBL612853 | null | null | null | Entamoeba histolytica | Entamoeba histolytica | false | ORGANISM | 5,759 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of amidines and sulfonamides of 5- and 6-amino-2,3-bis(4-alkyl-1-piperazinyl)quinoxalines was synthesized and tested against cecal and hepatic forms of Entamoeba histolytica infections in rats and hamsters, respectively. Four compounds (5, 6, 8, and 9) were found to have acceptable activity against infections in both species but were too toxic to be considered for use in man. | Fabio PF, Lang SA, Lin YI, Tomcufcik AS. | 10.1021/jm00176a017 | null | 201 | 2 | J Med Chem | null | 7,359,534 | 1 | Antiamebic amidines and sulfonamides of 5- and 6-amino-2,3-bis(4-alkyl-1-piperazinyl)quinoxalines. | 23 | 1,980 |
null | 34,394 | CHEMBL693881 | Lowest active dose which cured hamsters with Entamoeba histolytica hepatic infection was measured | F | BAO_0000218 | organism-based format | CCCN1CCN(c2nc3ccc(/N=C/N(C)C)cc3nc2N2CCN(CCC)CC2)CC1 | null | CHEMBL1121391 | J Med Chem | 1,980 | CHEMBL66079 | null | null | 0 | null | 110,555 | = | 1 | 0 | = | Dose | mg kg-1 day-1 | 100 | CHEMBL612853 | Entamoeba histolytica | Entamoeba histolytica | 5759 | null | Dose | mg kg-1 day-1 | UO_0000311 | 100.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCN1CCN(c2nc3ccc(/N=C/N(C)C)cc3nc2N2CCN(CCC)CC2)CC1 |
RDKit 2D
33 36 0 0 0 0 0 0 0 0999 V2000
5.7000 -6.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6917 -5.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9875 -6.6292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.9792 -4.9750 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4042 -4.9667 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4167 -6.6167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.2667 -6.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2667 -5.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1250 -6.6292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.4125 -6.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.8292 -4.1292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.8417 -7.4417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -6.6292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.1167 -5.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.1250 -6.2000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4000 -4.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL66079
> <chembl_pref_name>
None | InChI=1S/C25H40N8/c1-5-9-30-11-15-32(16-12-30)24-25(33-17-13-31(10-6-2)14-18-33)28-23-19-21(26-20-29(3)4)7-8-22(23)27-24/h7-8,19-20H,5-6,9-18H2,1-4H3/b26-20+ | PYQRPNZZTJLWTE-LHLOQNFPSA-N | 2.92 | 2 | C25H40N8 | 452.65 | 7 | 0 | 33 | 452.65 | -1.17 | 0 | 54.34 | 0.45 | N | 8 | CHEMBL66079 | CHEMBL66079 | CHEMBL66079 | null | null | null | null | Entamoeba histolytica | null | null | 5,759 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Lowest active dose which cured hamsters with Entamoeba histolytica hepatic infection was measured | CHEMBL1121391 | Non-molecular target assigned | N | null | 1 | CHEMBL612853 | null | null | null | Entamoeba histolytica | Entamoeba histolytica | false | ORGANISM | 5,759 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of amidines and sulfonamides of 5- and 6-amino-2,3-bis(4-alkyl-1-piperazinyl)quinoxalines was synthesized and tested against cecal and hepatic forms of Entamoeba histolytica infections in rats and hamsters, respectively. Four compounds (5, 6, 8, and 9) were found to have acceptable activity against infections in both species but were too toxic to be considered for use in man. | Fabio PF, Lang SA, Lin YI, Tomcufcik AS. | 10.1021/jm00176a017 | null | 201 | 2 | J Med Chem | null | 7,359,534 | 1 | Antiamebic amidines and sulfonamides of 5- and 6-amino-2,3-bis(4-alkyl-1-piperazinyl)quinoxalines. | 23 | 1,980 |
null | 34,395 | CHEMBL657542 | Ability to destroy fluid-phase human complement 1 in the presence of complement 4 with appropriate serial twofold dilutions of the test compound using C1 assay | B | BAO_0000019 | assay format | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 | null | CHEMBL1121398 | J Med Chem | 1,980 | CHEMBL265502 | SURAMIN | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 143,085 | = | 1 | 0 | = | ED50 | ug ml-1 | 21 | CHEMBL612545 | null | Unchecked | null | null | ED50 | ug ml-1 | UO_0000274 | 21.0 | null | null | null | null | null | 0 | 2 | null | null | 0 | 3.0 | Small molecule | 1 | false | false | 0 | SURAMIN | 0 | MOL | false | false | null | 1,997 | false | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 |
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M END
> <chembl_id>
CHEMBL265502
> <chembl_pref_name>
SURAMIN | InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80) | FIAFUQMPZJWCLV-UHFFFAOYSA-N | null | null | C51H40N6O23S6 | 1297.30 | null | null | null | 1,297.3 | null | null | null | null | null | null | CHEMBL265502 | CHEMBL265502 | CHEMBL265502 | Farma [OTHER] | FARMA-939 [RESEARCH_CODE] | Fourneau [OTHER] | Metaret [OTHER] | Naganol [OTHER] | NSC-34936 [RESEARCH_CODE] | Suramin [OTHER] | Suramine [OTHER] | null | null | null | Homo sapiens | null | null | 9,606 | null | B | Binding | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Ability to destroy fluid-phase human complement 1 in the presence of complement 4 with appropriate serial twofold dilutions of the test compound using C1 assay | CHEMBL1121398 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | Carcinoma, Non-Small-Cell Lung | non-small cell lung carcinoma | 2.0 | 1 | Conrow RB, Bauman N, Brockman JA, Bernstein S. | 10.1021/jm00177a006 | null | 240 | 3 | J Med Chem | null | 7,365,741 | 1 | Synthetic modulators of the complement system. 1. Synthesis and biological activity of 5,5',5''-[1,3,6-naphthalenetriyltris(sulfonylimino)]-tris[1,3-benzenedisulfonic acid] hexasodium salt. | 23 | 1,980 | |
null | 34,396 | CHEMBL706266 | The ability to inhibit late component of human complement (C3-C9) using C-late assay | B | BAO_0000019 | assay format | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 | null | CHEMBL1121398 | J Med Chem | 1,980 | CHEMBL265502 | SURAMIN | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 143,085 | = | 1 | 0 | = | ED50 | ug ml-1 | 50 | CHEMBL612545 | null | Unchecked | null | null | ED50 | ug ml-1 | UO_0000274 | 50.0 | null | null | null | null | null | 0 | 2 | null | null | 0 | 3.0 | Small molecule | 1 | false | false | 0 | SURAMIN | 0 | MOL | false | false | null | 1,997 | false | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 |
RDKit 2D
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M END
> <chembl_id>
CHEMBL265502
> <chembl_pref_name>
SURAMIN | InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80) | FIAFUQMPZJWCLV-UHFFFAOYSA-N | null | null | C51H40N6O23S6 | 1297.30 | null | null | null | 1,297.3 | null | null | null | null | null | null | CHEMBL265502 | CHEMBL265502 | CHEMBL265502 | Farma [OTHER] | FARMA-939 [RESEARCH_CODE] | Fourneau [OTHER] | Metaret [OTHER] | Naganol [OTHER] | NSC-34936 [RESEARCH_CODE] | Suramin [OTHER] | Suramine [OTHER] | null | null | null | Homo sapiens | null | null | 9,606 | null | B | Binding | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | The ability to inhibit late component of human complement (C3-C9) using C-late assay | CHEMBL1121398 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | Carcinoma, Non-Small-Cell Lung | non-small cell lung carcinoma | 2.0 | 1 | Conrow RB, Bauman N, Brockman JA, Bernstein S. | 10.1021/jm00177a006 | null | 240 | 3 | J Med Chem | null | 7,365,741 | 1 | Synthetic modulators of the complement system. 1. Synthesis and biological activity of 5,5',5''-[1,3,6-naphthalenetriyltris(sulfonylimino)]-tris[1,3-benzenedisulfonic acid] hexasodium salt. | 23 | 1,980 | |
null | 34,397 | CHEMBL657541 | Inhibition of the complement alternative pathway by Mercaptan-treated human erythrocytes lyse in autologous serum via the alternative pathway activated by cobra venom factor in the presence of appropriate serial twofold dilutions of the test compound | B | BAO_0000366 | cell-free format | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 | null | CHEMBL1121398 | J Med Chem | 1,980 | CHEMBL265502 | SURAMIN | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 143,085 | = | 1 | 0 | = | ED50 | ug ml-1 | 167 | CHEMBL612546 | null | Molecular identity unknown | null | null | ED50 | ug ml-1 | UO_0000274 | 167.0 | null | null | null | null | null | 0 | 2 | null | null | 0 | 3.0 | Small molecule | 1 | false | false | 0 | SURAMIN | 0 | MOL | false | false | null | 1,997 | false | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 |
RDKit 2D
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M END
> <chembl_id>
CHEMBL265502
> <chembl_pref_name>
SURAMIN | InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80) | FIAFUQMPZJWCLV-UHFFFAOYSA-N | null | null | C51H40N6O23S6 | 1297.30 | null | null | null | 1,297.3 | null | null | null | null | null | null | CHEMBL265502 | CHEMBL265502 | CHEMBL265502 | Farma [OTHER] | FARMA-939 [RESEARCH_CODE] | Fourneau [OTHER] | Metaret [OTHER] | Naganol [OTHER] | NSC-34936 [RESEARCH_CODE] | Suramin [OTHER] | Suramine [OTHER] | null | null | null | Homo sapiens | null | null | 9,606 | Serum | B | Binding | BAO_0000366 | cell-free format | null | Target assigned is molecular non-protein target | 3 | Inhibition of the complement alternative pathway by Mercaptan-treated human erythrocytes lyse in autologous serum via the alternative pathway activated by cobra venom factor in the presence of appropriate serial twofold dilutions of the test compound | CHEMBL1121398 | Molecular target other than protein assigned | M | null | 1 | CHEMBL612546 | CHEMBL3638229 | null | null | null | Molecular identity unknown | false | UNKNOWN | null | null | null | null | null | 0 | null | null | null | null | null | null | null | Carcinoma, Non-Small-Cell Lung | non-small cell lung carcinoma | 2.0 | 1 | Conrow RB, Bauman N, Brockman JA, Bernstein S. | 10.1021/jm00177a006 | null | 240 | 3 | J Med Chem | null | 7,365,741 | 1 | Synthetic modulators of the complement system. 1. Synthesis and biological activity of 5,5',5''-[1,3,6-naphthalenetriyltris(sulfonylimino)]-tris[1,3-benzenedisulfonic acid] hexasodium salt. | 23 | 1,980 | |
null | 34,398 | CHEMBL694631 | Evaluated in vitro for complement activity using guinea pig serum was determined by cap 50 assay | F | BAO_0000218 | organism-based format | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 | null | CHEMBL1121398 | J Med Chem | 1,980 | CHEMBL265502 | SURAMIN | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 143,085 | = | 1 | 0 | = | ED50 | ug ml-1 | 603 | CHEMBL369 | Cavia porcellus | Cavia porcellus | 10141 | null | ED50 | ug ml-1 | UO_0000274 | 603.0 | null | null | null | null | null | 0 | 2 | null | null | 0 | 3.0 | Small molecule | 1 | false | false | 0 | SURAMIN | 0 | MOL | false | false | null | 1,997 | false | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 |
RDKit 2D
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M END
> <chembl_id>
CHEMBL265502
> <chembl_pref_name>
SURAMIN | InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80) | FIAFUQMPZJWCLV-UHFFFAOYSA-N | null | null | C51H40N6O23S6 | 1297.30 | null | null | null | 1,297.3 | null | null | null | null | null | null | CHEMBL265502 | CHEMBL265502 | CHEMBL265502 | Farma [OTHER] | FARMA-939 [RESEARCH_CODE] | Fourneau [OTHER] | Metaret [OTHER] | Naganol [OTHER] | NSC-34936 [RESEARCH_CODE] | Suramin [OTHER] | Suramine [OTHER] | null | null | null | Cavia porcellus | null | null | 10,141 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Evaluated in vitro for complement activity using guinea pig serum was determined by cap 50 assay | CHEMBL1121398 | Non-molecular target assigned | N | null | 1 | CHEMBL369 | null | null | null | Cavia porcellus | Cavia porcellus | false | ORGANISM | 10,141 | null | null | null | null | 0 | null | null | null | null | null | null | null | Carcinoma, Non-Small-Cell Lung | non-small cell lung carcinoma | 2.0 | 1 | Conrow RB, Bauman N, Brockman JA, Bernstein S. | 10.1021/jm00177a006 | null | 240 | 3 | J Med Chem | null | 7,365,741 | 1 | Synthetic modulators of the complement system. 1. Synthesis and biological activity of 5,5',5''-[1,3,6-naphthalenetriyltris(sulfonylimino)]-tris[1,3-benzenedisulfonic acid] hexasodium salt. | 23 | 1,980 | |
null | 34,399 | CHEMBL685960 | Evaluated in vivo after intraperitoneal administration by guinea pig assay | F | BAO_0000218 | organism-based format | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 | null | CHEMBL1121398 | J Med Chem | 1,980 | CHEMBL265502 | SURAMIN | null | 0 | http://qudt.org/vocab/unit#Percent | 143,085 | = | 1 | 1 | = | Inhibition | % | 44 | CHEMBL369 | Cavia porcellus | Cavia porcellus | 10141 | null | Inhibition | % | UO_0000187 | 44.0 | null | null | null | null | null | 0 | 2 | null | null | 0 | 3.0 | Small molecule | 1 | false | false | 0 | SURAMIN | 0 | MOL | false | false | null | 1,997 | false | Cc1ccc(C(=O)Nc2ccc(S(=O)(=O)O)c3cc(S(=O)(=O)O)cc(S(=O)(=O)O)c23)cc1NC(=O)c1cccc(NC(=O)Nc2cccc(C(=O)Nc3cc(C(=O)Nc4ccc(S(=O)(=O)O)c5cc(S(=O)(=O)O)cc(S(=O)(=O)O)c45)ccc3C)c2)c1 |
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M END
> <chembl_id>
CHEMBL265502
> <chembl_pref_name>
SURAMIN | InChI=1S/C51H40N6O23S6/c1-25-9-11-29(49(60)54-37-13-15-41(83(69,70)71)35-21-33(81(63,64)65)23-43(45(35)37)85(75,76)77)19-39(25)56-47(58)27-5-3-7-31(17-27)52-51(62)53-32-8-4-6-28(18-32)48(59)57-40-20-30(12-10-26(40)2)50(61)55-38-14-16-42(84(72,73)74)36-22-34(82(66,67)68)24-44(46(36)38)86(78,79)80/h3-24H,1-2H3,(H,54,60)(H,55,61)(H,56,58)(H,57,59)(H2,52,53,62)(H,63,64,65)(H,66,67,68)(H,69,70,71)(H,72,73,74)(H,75,76,77)(H,78,79,80) | FIAFUQMPZJWCLV-UHFFFAOYSA-N | null | null | C51H40N6O23S6 | 1297.30 | null | null | null | 1,297.3 | null | null | null | null | null | null | CHEMBL265502 | CHEMBL265502 | CHEMBL265502 | Farma [OTHER] | FARMA-939 [RESEARCH_CODE] | Fourneau [OTHER] | Metaret [OTHER] | Naganol [OTHER] | NSC-34936 [RESEARCH_CODE] | Suramin [OTHER] | Suramine [OTHER] | null | null | null | Cavia porcellus | null | null | 10,141 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Evaluated in vivo after intraperitoneal administration by guinea pig assay | CHEMBL1121398 | Non-molecular target assigned | N | null | 1 | CHEMBL369 | null | null | null | Cavia porcellus | Cavia porcellus | false | ORGANISM | 10,141 | null | null | null | null | 0 | null | null | null | null | null | null | null | Carcinoma, Non-Small-Cell Lung | non-small cell lung carcinoma | 2.0 | 1 | Conrow RB, Bauman N, Brockman JA, Bernstein S. | 10.1021/jm00177a006 | null | 240 | 3 | J Med Chem | null | 7,365,741 | 1 | Synthetic modulators of the complement system. 1. Synthesis and biological activity of 5,5',5''-[1,3,6-naphthalenetriyltris(sulfonylimino)]-tris[1,3-benzenedisulfonic acid] hexasodium salt. | 23 | 1,980 | |
null | 34,400 | CHEMBL778496 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 40 mg/kg in conscious renal hypertensive rats (RHR). | F | BAO_0000218 | organism-based format | O=C(Nc1ccccc1)NC1CCN(CCCC(=O)c2ccccc2)CC1 | null | CHEMBL1121617 | J Med Chem | 1,980 | CHEMBL354681 | null | null | 0 | null | 334,500 | = | 1 | 0 | = | Activity | null | 39 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Activity | null | null | 39.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(Nc1ccccc1)NC1CCN(CCCC(=O)c2ccccc2)CC1 |
RDKit 2D
27 29 0 0 0 0 0 0 0 0999 V2000
6.5417 -2.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4167 -1.5292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.1500 -1.9875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.2292 -1.4875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.7167 -0.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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5.6292 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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1.3792 0.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2 13 1 0
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M END
> <chembl_id>
CHEMBL354681
> <chembl_pref_name>
None | InChI=1S/C22H27N3O2/c26-21(18-8-3-1-4-9-18)12-7-15-25-16-13-20(14-17-25)24-22(27)23-19-10-5-2-6-11-19/h1-6,8-11,20H,7,12-17H2,(H2,23,24,27) | DEWQQKPKUSHDOB-UHFFFAOYSA-N | 3.94 | 2 | C22H27N3O2 | 365.48 | 3 | 2 | 27 | 365.48 | -1.38 | 0 | 61.44 | 0.73 | N | 7 | CHEMBL354681 | CHEMBL354681 | CHEMBL354681 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 40 mg/kg in conscious renal hypertensive rats (RHR). | CHEMBL1121617 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | DOSE=40.0 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series. | Archibald JL, Beardsley DR, Bisset GM, Fairbrother P, Jackson JL, Opalko A, Ward TJ. | 10.1021/jm00182a009 | null | 857 | 8 | J Med Chem | null | 7,401,114 | 1 | Antihypertensive ureidopiperidines. | 23 | 1,980 |
null | 35,607 | CHEMBL782626 | Percent inhibition of PCA reaction in anesthetized rats at 11.7 mg/kg peroral administration for 3 hr | F | BAO_0000218 | organism-based format | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O | null | CHEMBL1121553 | J Med Chem | 1,980 | CHEMBL1355736 | THEOPHYLLINE | null | 0 | http://qudt.org/vocab/unit#Percent | 22,463 | = | 1 | 1 | = | Inhibition | % | 25.1 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Inhibition | % | UO_0000187 | 25.1 | null | null | null | null | 1 | 0 | 2 | 1,976 | null | 0 | 4.0 | Protein | 0 | true | true | 0 | THEOPHYLLINE | 0 | MOL | true | false | null | null | false | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O |
RDKit 2D
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7.2137 -6.3752 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -5.0314 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.6992 -5.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -6.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -7.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 5 1 0
5 2 1 0
6 3 2 0
7 4 1 0
8 3 1 0
9 6 1 0
10 8 1 0
11 5 2 0
12 7 2 0
13 2 1 0
14 4 1 0
6 7 1 0
9 10 2 0
M END
> <chembl_id>
CHEMBL1355736
> <chembl_pref_name>
THEOPHYLLINE | InChI=1S/C7H8N4O2.H2O/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;/h3H,1-2H3,(H,8,9);1H2 | INQSMEFCAIHTJG-UHFFFAOYSA-N | -1.04 | 2 | C7H10N4O3 | 198.18 | 5 | 1 | 13 | 180.17 | -0.75 | 0 | 72.68 | 0.56 | N | 0 | CHEMBL190 | CHEMBL1355736 | CHEMBL190 | Accurbron [TRADE_NAME] | Aerolate [TRADE_NAME] | Aerolate iii [TRADE_NAME] | Aerolate jr [TRADE_NAME] | Aerolate sr [TRADE_NAME] | Aquaphyllin [TRADE_NAME] | Bronkodyl [TRADE_NAME] | Duraphyl [TRADE_NAME] | Elixicon [TRADE_NAME] | Elixomin [TRADE_NAME] | Elixophyllin [TRADE_NAME] | Elixophyllin sr [TRADE_NAME] | Labid [TRADE_NAME] | Lanophyllin [TRADE_NAME] | Lasma [TRADE_NAME] | NSC-757346 [RESEARCH_CODE] | Nuelin [TRADE_NAME] | Nuelin sa [TRADE_NAME] | Nuelin sa-250 [TRADE_NAME] | Pro-vent [TRADE_NAME] | Quibron-t [TRADE_NAME] | Quibron-t/sr [TRADE_NAME] | Slo-bid [TRADE_NAME] | Slo-phyllin [TRADE_NAME] | Somophyllin-crt [TRADE_NAME] | Somophyllin-t [TRADE_NAME] | Sustaire [TRADE_NAME] | Theo-24 [TRADE_NAME] | Theobid [TRADE_NAME] | Theobid jr. [TRADE_NAME] | Theochron [TRADE_NAME] | Theocin [TRADE_NAME] | Theoclear-100 [TRADE_NAME] | Theoclear-200 [TRADE_NAME] | Theoclear-80 [TRADE_NAME] | Theoclear l.a.-130 [TRADE_NAME] | Theoclear l.a.-260 [TRADE_NAME] | Theo-dur [TRADE_NAME] | Theograd [TRADE_NAME] | Theolair [TRADE_NAME] | Theolair-sr [TRADE_NAME] | Theolixir [TRADE_NAME] | Theophyl [TRADE_NAME] | Theophyl-225 [TRADE_NAME] | Theophylline [ATC] | Theophylline [BNF] | Theophylline [FDA] | Theophylline [MERCK_INDEX] | Theophylline [OTHER] | Theophylline [TRADE_NAME] | Theophylline 0.04% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.08% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.16% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.2% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.32% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.4% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline and dextrose 5% in plastic container [TRADE_NAME] | Theophylline component of dicurin procaine [TRADE_NAME] | Theophylline component of mersalyl- [TRADE_NAME] | Theophylline in dextrose 5% in plastic container [TRADE_NAME] | Theophylline monohydrate [OTHER] | Theophylline-sr [TRADE_NAME] | Theophyl-sr [TRADE_NAME] | Theovent [TRADE_NAME] | T-phyl [TRADE_NAME] | Uni-dur [TRADE_NAME] | Uniphyl [TRADE_NAME] | Uniphyllin continus [TRADE_NAME] | DailyMed:theophylline | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Percent inhibition of PCA reaction in anesthetized rats at 11.7 mg/kg peroral administration for 3 hr | CHEMBL1121553 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | DOSE=11.7 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | Phosphodiesterase 4 inhibitor | Phosphodiesterase 3 inhibitor | Adenosine receptor antagonist | INHIBITOR | ANTAGONIST | 1 | 1 | null | null | null | Pulmonary Disease, Chronic Obstructive | Lung Diseases, Obstructive | Renal Insufficiency, Chronic | Leukemia, Myeloid, Acute | Leukemia | Hypertension, Pulmonary | Prostatic Neoplasms | Carcinoma, Non-Small-Cell Lung | Kidney Diseases | Altitude Sickness | Virus Diseases | Respiratory Insufficiency | Apnea | Depressive Disorder, Major | Pseudohypoparathyroidism | Depressive Disorder | Bronchitis, Chronic | Asthma | Hernias, Diaphragmatic, Congenital | Lung Neoplasms | Severe Acute Respiratory Syndrome | chronic obstructive pulmonary disease | Airway obstruction | chronic kidney disease | acute myeloid leukemia | leukemia | pulmonary arterial hypertension | prostate carcinoma | non-small cell lung carcinoma | kidney disease | altitude sickness | viral disease | respiratory failure | Apnea | major depressive disorder | Albright hereditary osteodystrophy | depressive disorder | chronic bronchitis | asthma | pseudohypoparathyroidism type 1A | pseudohypoparathyroidism | congenital heart disease | lung cancer | COVID-19 | 4.0 | 23 | The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat. | Temple DL, Yevich JP, Catt JD, Owens D, Hanning C, Covington RR, Seidehamel RJ, Dungan KW. | 10.1021/jm00185a008 | null | 1188 | 11 | J Med Chem | null | 6,161,252 | 1 | Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones. | 23 | 1,980 |
null | 35,608 | CHEMBL783956 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 15 min | F | BAO_0000218 | organism-based format | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O | null | CHEMBL1121553 | J Med Chem | 1,980 | CHEMBL1355736 | THEOPHYLLINE | null | 0 | http://qudt.org/vocab/unit#Percent | 22,463 | = | 1 | 1 | = | Inhibition | % | 51.9 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Inhibition | % | UO_0000187 | 51.9 | null | null | null | null | 1 | 0 | 2 | 1,976 | null | 0 | 4.0 | Protein | 0 | true | true | 0 | THEOPHYLLINE | 0 | MOL | true | false | null | null | false | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O |
RDKit 2D
14 14 0 0 0 0 0 0 0 0999 V2000
8.9134 -7.3176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -6.5370 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -5.2865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -5.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -6.3752 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -5.0314 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.6992 -5.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -6.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -7.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 5 1 0
5 2 1 0
6 3 2 0
7 4 1 0
8 3 1 0
9 6 1 0
10 8 1 0
11 5 2 0
12 7 2 0
13 2 1 0
14 4 1 0
6 7 1 0
9 10 2 0
M END
> <chembl_id>
CHEMBL1355736
> <chembl_pref_name>
THEOPHYLLINE | InChI=1S/C7H8N4O2.H2O/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;/h3H,1-2H3,(H,8,9);1H2 | INQSMEFCAIHTJG-UHFFFAOYSA-N | -1.04 | 2 | C7H10N4O3 | 198.18 | 5 | 1 | 13 | 180.17 | -0.75 | 0 | 72.68 | 0.56 | N | 0 | CHEMBL190 | CHEMBL1355736 | CHEMBL190 | Accurbron [TRADE_NAME] | Aerolate [TRADE_NAME] | Aerolate iii [TRADE_NAME] | Aerolate jr [TRADE_NAME] | Aerolate sr [TRADE_NAME] | Aquaphyllin [TRADE_NAME] | Bronkodyl [TRADE_NAME] | Duraphyl [TRADE_NAME] | Elixicon [TRADE_NAME] | Elixomin [TRADE_NAME] | Elixophyllin [TRADE_NAME] | Elixophyllin sr [TRADE_NAME] | Labid [TRADE_NAME] | Lanophyllin [TRADE_NAME] | Lasma [TRADE_NAME] | NSC-757346 [RESEARCH_CODE] | Nuelin [TRADE_NAME] | Nuelin sa [TRADE_NAME] | Nuelin sa-250 [TRADE_NAME] | Pro-vent [TRADE_NAME] | Quibron-t [TRADE_NAME] | Quibron-t/sr [TRADE_NAME] | Slo-bid [TRADE_NAME] | Slo-phyllin [TRADE_NAME] | Somophyllin-crt [TRADE_NAME] | Somophyllin-t [TRADE_NAME] | Sustaire [TRADE_NAME] | Theo-24 [TRADE_NAME] | Theobid [TRADE_NAME] | Theobid jr. [TRADE_NAME] | Theochron [TRADE_NAME] | Theocin [TRADE_NAME] | Theoclear-100 [TRADE_NAME] | Theoclear-200 [TRADE_NAME] | Theoclear-80 [TRADE_NAME] | Theoclear l.a.-130 [TRADE_NAME] | Theoclear l.a.-260 [TRADE_NAME] | Theo-dur [TRADE_NAME] | Theograd [TRADE_NAME] | Theolair [TRADE_NAME] | Theolair-sr [TRADE_NAME] | Theolixir [TRADE_NAME] | Theophyl [TRADE_NAME] | Theophyl-225 [TRADE_NAME] | Theophylline [ATC] | Theophylline [BNF] | Theophylline [FDA] | Theophylline [MERCK_INDEX] | Theophylline [OTHER] | Theophylline [TRADE_NAME] | Theophylline 0.04% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.08% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.16% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.2% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.32% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.4% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline and dextrose 5% in plastic container [TRADE_NAME] | Theophylline component of dicurin procaine [TRADE_NAME] | Theophylline component of mersalyl- [TRADE_NAME] | Theophylline in dextrose 5% in plastic container [TRADE_NAME] | Theophylline monohydrate [OTHER] | Theophylline-sr [TRADE_NAME] | Theophyl-sr [TRADE_NAME] | Theovent [TRADE_NAME] | T-phyl [TRADE_NAME] | Uni-dur [TRADE_NAME] | Uniphyl [TRADE_NAME] | Uniphyllin continus [TRADE_NAME] | DailyMed:theophylline | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 15 min | CHEMBL1121553 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | DOSE=47.6 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | Phosphodiesterase 4 inhibitor | Phosphodiesterase 3 inhibitor | Adenosine receptor antagonist | INHIBITOR | ANTAGONIST | 1 | 1 | null | null | null | Pulmonary Disease, Chronic Obstructive | Lung Diseases, Obstructive | Renal Insufficiency, Chronic | Leukemia, Myeloid, Acute | Leukemia | Hypertension, Pulmonary | Prostatic Neoplasms | Carcinoma, Non-Small-Cell Lung | Kidney Diseases | Altitude Sickness | Virus Diseases | Respiratory Insufficiency | Apnea | Depressive Disorder, Major | Pseudohypoparathyroidism | Depressive Disorder | Bronchitis, Chronic | Asthma | Hernias, Diaphragmatic, Congenital | Lung Neoplasms | Severe Acute Respiratory Syndrome | chronic obstructive pulmonary disease | Airway obstruction | chronic kidney disease | acute myeloid leukemia | leukemia | pulmonary arterial hypertension | prostate carcinoma | non-small cell lung carcinoma | kidney disease | altitude sickness | viral disease | respiratory failure | Apnea | major depressive disorder | Albright hereditary osteodystrophy | depressive disorder | chronic bronchitis | asthma | pseudohypoparathyroidism type 1A | pseudohypoparathyroidism | congenital heart disease | lung cancer | COVID-19 | 4.0 | 23 | The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat. | Temple DL, Yevich JP, Catt JD, Owens D, Hanning C, Covington RR, Seidehamel RJ, Dungan KW. | 10.1021/jm00185a008 | null | 1188 | 11 | J Med Chem | null | 6,161,252 | 1 | Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones. | 23 | 1,980 |
null | 35,609 | CHEMBL782624 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 3 hr | F | BAO_0000218 | organism-based format | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O | null | CHEMBL1121553 | J Med Chem | 1,980 | CHEMBL1355736 | THEOPHYLLINE | null | 0 | http://qudt.org/vocab/unit#Percent | 22,463 | = | 1 | 1 | = | Inhibition | % | 52.5 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Inhibition | % | UO_0000187 | 52.5 | null | null | null | null | 1 | 0 | 2 | 1,976 | null | 0 | 4.0 | Protein | 0 | true | true | 0 | THEOPHYLLINE | 0 | MOL | true | false | null | null | false | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O |
RDKit 2D
14 14 0 0 0 0 0 0 0 0999 V2000
8.9134 -7.3176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -6.5370 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -5.2865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -5.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -6.3752 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -5.0314 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.6992 -5.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -6.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -7.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 5 1 0
5 2 1 0
6 3 2 0
7 4 1 0
8 3 1 0
9 6 1 0
10 8 1 0
11 5 2 0
12 7 2 0
13 2 1 0
14 4 1 0
6 7 1 0
9 10 2 0
M END
> <chembl_id>
CHEMBL1355736
> <chembl_pref_name>
THEOPHYLLINE | InChI=1S/C7H8N4O2.H2O/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;/h3H,1-2H3,(H,8,9);1H2 | INQSMEFCAIHTJG-UHFFFAOYSA-N | -1.04 | 2 | C7H10N4O3 | 198.18 | 5 | 1 | 13 | 180.17 | -0.75 | 0 | 72.68 | 0.56 | N | 0 | CHEMBL190 | CHEMBL1355736 | CHEMBL190 | Accurbron [TRADE_NAME] | Aerolate [TRADE_NAME] | Aerolate iii [TRADE_NAME] | Aerolate jr [TRADE_NAME] | Aerolate sr [TRADE_NAME] | Aquaphyllin [TRADE_NAME] | Bronkodyl [TRADE_NAME] | Duraphyl [TRADE_NAME] | Elixicon [TRADE_NAME] | Elixomin [TRADE_NAME] | Elixophyllin [TRADE_NAME] | Elixophyllin sr [TRADE_NAME] | Labid [TRADE_NAME] | Lanophyllin [TRADE_NAME] | Lasma [TRADE_NAME] | NSC-757346 [RESEARCH_CODE] | Nuelin [TRADE_NAME] | Nuelin sa [TRADE_NAME] | Nuelin sa-250 [TRADE_NAME] | Pro-vent [TRADE_NAME] | Quibron-t [TRADE_NAME] | Quibron-t/sr [TRADE_NAME] | Slo-bid [TRADE_NAME] | Slo-phyllin [TRADE_NAME] | Somophyllin-crt [TRADE_NAME] | Somophyllin-t [TRADE_NAME] | Sustaire [TRADE_NAME] | Theo-24 [TRADE_NAME] | Theobid [TRADE_NAME] | Theobid jr. [TRADE_NAME] | Theochron [TRADE_NAME] | Theocin [TRADE_NAME] | Theoclear-100 [TRADE_NAME] | Theoclear-200 [TRADE_NAME] | Theoclear-80 [TRADE_NAME] | Theoclear l.a.-130 [TRADE_NAME] | Theoclear l.a.-260 [TRADE_NAME] | Theo-dur [TRADE_NAME] | Theograd [TRADE_NAME] | Theolair [TRADE_NAME] | Theolair-sr [TRADE_NAME] | Theolixir [TRADE_NAME] | Theophyl [TRADE_NAME] | Theophyl-225 [TRADE_NAME] | Theophylline [ATC] | Theophylline [BNF] | Theophylline [FDA] | Theophylline [MERCK_INDEX] | Theophylline [OTHER] | Theophylline [TRADE_NAME] | Theophylline 0.04% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.08% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.16% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.2% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.32% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.4% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline and dextrose 5% in plastic container [TRADE_NAME] | Theophylline component of dicurin procaine [TRADE_NAME] | Theophylline component of mersalyl- [TRADE_NAME] | Theophylline in dextrose 5% in plastic container [TRADE_NAME] | Theophylline monohydrate [OTHER] | Theophylline-sr [TRADE_NAME] | Theophyl-sr [TRADE_NAME] | Theovent [TRADE_NAME] | T-phyl [TRADE_NAME] | Uni-dur [TRADE_NAME] | Uniphyl [TRADE_NAME] | Uniphyllin continus [TRADE_NAME] | DailyMed:theophylline | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 3 hr | CHEMBL1121553 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | DOSE=47.6 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | Phosphodiesterase 4 inhibitor | Phosphodiesterase 3 inhibitor | Adenosine receptor antagonist | INHIBITOR | ANTAGONIST | 1 | 1 | null | null | null | Pulmonary Disease, Chronic Obstructive | Lung Diseases, Obstructive | Renal Insufficiency, Chronic | Leukemia, Myeloid, Acute | Leukemia | Hypertension, Pulmonary | Prostatic Neoplasms | Carcinoma, Non-Small-Cell Lung | Kidney Diseases | Altitude Sickness | Virus Diseases | Respiratory Insufficiency | Apnea | Depressive Disorder, Major | Pseudohypoparathyroidism | Depressive Disorder | Bronchitis, Chronic | Asthma | Hernias, Diaphragmatic, Congenital | Lung Neoplasms | Severe Acute Respiratory Syndrome | chronic obstructive pulmonary disease | Airway obstruction | chronic kidney disease | acute myeloid leukemia | leukemia | pulmonary arterial hypertension | prostate carcinoma | non-small cell lung carcinoma | kidney disease | altitude sickness | viral disease | respiratory failure | Apnea | major depressive disorder | Albright hereditary osteodystrophy | depressive disorder | chronic bronchitis | asthma | pseudohypoparathyroidism type 1A | pseudohypoparathyroidism | congenital heart disease | lung cancer | COVID-19 | 4.0 | 23 | The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat. | Temple DL, Yevich JP, Catt JD, Owens D, Hanning C, Covington RR, Seidehamel RJ, Dungan KW. | 10.1021/jm00185a008 | null | 1188 | 11 | J Med Chem | null | 6,161,252 | 1 | Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones. | 23 | 1,980 |
null | 35,610 | CHEMBL782625 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 6 hr | F | BAO_0000218 | organism-based format | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O | null | CHEMBL1121553 | J Med Chem | 1,980 | CHEMBL1355736 | THEOPHYLLINE | null | 0 | http://qudt.org/vocab/unit#Percent | 22,463 | = | 1 | 1 | = | Inhibition | % | 13 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Inhibition | % | UO_0000187 | 13.0 | null | null | null | null | 1 | 0 | 2 | 1,976 | null | 0 | 4.0 | Protein | 0 | true | true | 0 | THEOPHYLLINE | 0 | MOL | true | false | null | null | false | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O |
RDKit 2D
14 14 0 0 0 0 0 0 0 0999 V2000
8.9134 -7.3176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -6.5370 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -5.2865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -5.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -6.3752 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -5.0314 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.6992 -5.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -6.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -7.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 5 1 0
5 2 1 0
6 3 2 0
7 4 1 0
8 3 1 0
9 6 1 0
10 8 1 0
11 5 2 0
12 7 2 0
13 2 1 0
14 4 1 0
6 7 1 0
9 10 2 0
M END
> <chembl_id>
CHEMBL1355736
> <chembl_pref_name>
THEOPHYLLINE | InChI=1S/C7H8N4O2.H2O/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;/h3H,1-2H3,(H,8,9);1H2 | INQSMEFCAIHTJG-UHFFFAOYSA-N | -1.04 | 2 | C7H10N4O3 | 198.18 | 5 | 1 | 13 | 180.17 | -0.75 | 0 | 72.68 | 0.56 | N | 0 | CHEMBL190 | CHEMBL1355736 | CHEMBL190 | Accurbron [TRADE_NAME] | Aerolate [TRADE_NAME] | Aerolate iii [TRADE_NAME] | Aerolate jr [TRADE_NAME] | Aerolate sr [TRADE_NAME] | Aquaphyllin [TRADE_NAME] | Bronkodyl [TRADE_NAME] | Duraphyl [TRADE_NAME] | Elixicon [TRADE_NAME] | Elixomin [TRADE_NAME] | Elixophyllin [TRADE_NAME] | Elixophyllin sr [TRADE_NAME] | Labid [TRADE_NAME] | Lanophyllin [TRADE_NAME] | Lasma [TRADE_NAME] | NSC-757346 [RESEARCH_CODE] | Nuelin [TRADE_NAME] | Nuelin sa [TRADE_NAME] | Nuelin sa-250 [TRADE_NAME] | Pro-vent [TRADE_NAME] | Quibron-t [TRADE_NAME] | Quibron-t/sr [TRADE_NAME] | Slo-bid [TRADE_NAME] | Slo-phyllin [TRADE_NAME] | Somophyllin-crt [TRADE_NAME] | Somophyllin-t [TRADE_NAME] | Sustaire [TRADE_NAME] | Theo-24 [TRADE_NAME] | Theobid [TRADE_NAME] | Theobid jr. [TRADE_NAME] | Theochron [TRADE_NAME] | Theocin [TRADE_NAME] | Theoclear-100 [TRADE_NAME] | Theoclear-200 [TRADE_NAME] | Theoclear-80 [TRADE_NAME] | Theoclear l.a.-130 [TRADE_NAME] | Theoclear l.a.-260 [TRADE_NAME] | Theo-dur [TRADE_NAME] | Theograd [TRADE_NAME] | Theolair [TRADE_NAME] | Theolair-sr [TRADE_NAME] | Theolixir [TRADE_NAME] | Theophyl [TRADE_NAME] | Theophyl-225 [TRADE_NAME] | Theophylline [ATC] | Theophylline [BNF] | Theophylline [FDA] | Theophylline [MERCK_INDEX] | Theophylline [OTHER] | Theophylline [TRADE_NAME] | Theophylline 0.04% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.08% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.16% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.2% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.32% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.4% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline and dextrose 5% in plastic container [TRADE_NAME] | Theophylline component of dicurin procaine [TRADE_NAME] | Theophylline component of mersalyl- [TRADE_NAME] | Theophylline in dextrose 5% in plastic container [TRADE_NAME] | Theophylline monohydrate [OTHER] | Theophylline-sr [TRADE_NAME] | Theophyl-sr [TRADE_NAME] | Theovent [TRADE_NAME] | T-phyl [TRADE_NAME] | Uni-dur [TRADE_NAME] | Uniphyl [TRADE_NAME] | Uniphyllin continus [TRADE_NAME] | DailyMed:theophylline | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 6 hr | CHEMBL1121553 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | DOSE=47.6 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | Phosphodiesterase 4 inhibitor | Phosphodiesterase 3 inhibitor | Adenosine receptor antagonist | INHIBITOR | ANTAGONIST | 1 | 1 | null | null | null | Pulmonary Disease, Chronic Obstructive | Lung Diseases, Obstructive | Renal Insufficiency, Chronic | Leukemia, Myeloid, Acute | Leukemia | Hypertension, Pulmonary | Prostatic Neoplasms | Carcinoma, Non-Small-Cell Lung | Kidney Diseases | Altitude Sickness | Virus Diseases | Respiratory Insufficiency | Apnea | Depressive Disorder, Major | Pseudohypoparathyroidism | Depressive Disorder | Bronchitis, Chronic | Asthma | Hernias, Diaphragmatic, Congenital | Lung Neoplasms | Severe Acute Respiratory Syndrome | chronic obstructive pulmonary disease | Airway obstruction | chronic kidney disease | acute myeloid leukemia | leukemia | pulmonary arterial hypertension | prostate carcinoma | non-small cell lung carcinoma | kidney disease | altitude sickness | viral disease | respiratory failure | Apnea | major depressive disorder | Albright hereditary osteodystrophy | depressive disorder | chronic bronchitis | asthma | pseudohypoparathyroidism type 1A | pseudohypoparathyroidism | congenital heart disease | lung cancer | COVID-19 | 4.0 | 23 | The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat. | Temple DL, Yevich JP, Catt JD, Owens D, Hanning C, Covington RR, Seidehamel RJ, Dungan KW. | 10.1021/jm00185a008 | null | 1188 | 11 | J Med Chem | null | 6,161,252 | 1 | Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones. | 23 | 1,980 |
null | 35,611 | CHEMBL782623 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 24 hr r | F | BAO_0000218 | organism-based format | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O | null | CHEMBL1121553 | J Med Chem | 1,980 | CHEMBL1355736 | THEOPHYLLINE | null | 0 | http://qudt.org/vocab/unit#Percent | 22,463 | = | 1 | 1 | = | Inhibition | % | 0 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Inhibition | % | UO_0000187 | 0.0 | null | null | null | null | 1 | 0 | 2 | 1,976 | null | 0 | 4.0 | Protein | 0 | true | true | 0 | THEOPHYLLINE | 0 | MOL | true | false | null | null | false | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O |
RDKit 2D
14 14 0 0 0 0 0 0 0 0999 V2000
8.9134 -7.3176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -6.5370 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -5.2865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -5.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -6.3752 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -5.0314 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.6992 -5.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -6.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -7.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 5 1 0
5 2 1 0
6 3 2 0
7 4 1 0
8 3 1 0
9 6 1 0
10 8 1 0
11 5 2 0
12 7 2 0
13 2 1 0
14 4 1 0
6 7 1 0
9 10 2 0
M END
> <chembl_id>
CHEMBL1355736
> <chembl_pref_name>
THEOPHYLLINE | InChI=1S/C7H8N4O2.H2O/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;/h3H,1-2H3,(H,8,9);1H2 | INQSMEFCAIHTJG-UHFFFAOYSA-N | -1.04 | 2 | C7H10N4O3 | 198.18 | 5 | 1 | 13 | 180.17 | -0.75 | 0 | 72.68 | 0.56 | N | 0 | CHEMBL190 | CHEMBL1355736 | CHEMBL190 | Accurbron [TRADE_NAME] | Aerolate [TRADE_NAME] | Aerolate iii [TRADE_NAME] | Aerolate jr [TRADE_NAME] | Aerolate sr [TRADE_NAME] | Aquaphyllin [TRADE_NAME] | Bronkodyl [TRADE_NAME] | Duraphyl [TRADE_NAME] | Elixicon [TRADE_NAME] | Elixomin [TRADE_NAME] | Elixophyllin [TRADE_NAME] | Elixophyllin sr [TRADE_NAME] | Labid [TRADE_NAME] | Lanophyllin [TRADE_NAME] | Lasma [TRADE_NAME] | NSC-757346 [RESEARCH_CODE] | Nuelin [TRADE_NAME] | Nuelin sa [TRADE_NAME] | Nuelin sa-250 [TRADE_NAME] | Pro-vent [TRADE_NAME] | Quibron-t [TRADE_NAME] | Quibron-t/sr [TRADE_NAME] | Slo-bid [TRADE_NAME] | Slo-phyllin [TRADE_NAME] | Somophyllin-crt [TRADE_NAME] | Somophyllin-t [TRADE_NAME] | Sustaire [TRADE_NAME] | Theo-24 [TRADE_NAME] | Theobid [TRADE_NAME] | Theobid jr. [TRADE_NAME] | Theochron [TRADE_NAME] | Theocin [TRADE_NAME] | Theoclear-100 [TRADE_NAME] | Theoclear-200 [TRADE_NAME] | Theoclear-80 [TRADE_NAME] | Theoclear l.a.-130 [TRADE_NAME] | Theoclear l.a.-260 [TRADE_NAME] | Theo-dur [TRADE_NAME] | Theograd [TRADE_NAME] | Theolair [TRADE_NAME] | Theolair-sr [TRADE_NAME] | Theolixir [TRADE_NAME] | Theophyl [TRADE_NAME] | Theophyl-225 [TRADE_NAME] | Theophylline [ATC] | Theophylline [BNF] | Theophylline [FDA] | Theophylline [MERCK_INDEX] | Theophylline [OTHER] | Theophylline [TRADE_NAME] | Theophylline 0.04% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.08% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.16% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.2% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.32% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.4% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline and dextrose 5% in plastic container [TRADE_NAME] | Theophylline component of dicurin procaine [TRADE_NAME] | Theophylline component of mersalyl- [TRADE_NAME] | Theophylline in dextrose 5% in plastic container [TRADE_NAME] | Theophylline monohydrate [OTHER] | Theophylline-sr [TRADE_NAME] | Theophyl-sr [TRADE_NAME] | Theovent [TRADE_NAME] | T-phyl [TRADE_NAME] | Uni-dur [TRADE_NAME] | Uniphyl [TRADE_NAME] | Uniphyllin continus [TRADE_NAME] | DailyMed:theophylline | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Percent inhibition of PCA reaction in anesthetized rats at 47.6 mg/kg oral administration for 24 hr r | CHEMBL1121553 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | DOSE=47.6 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | Phosphodiesterase 4 inhibitor | Phosphodiesterase 3 inhibitor | Adenosine receptor antagonist | INHIBITOR | ANTAGONIST | 1 | 1 | null | null | null | Pulmonary Disease, Chronic Obstructive | Lung Diseases, Obstructive | Renal Insufficiency, Chronic | Leukemia, Myeloid, Acute | Leukemia | Hypertension, Pulmonary | Prostatic Neoplasms | Carcinoma, Non-Small-Cell Lung | Kidney Diseases | Altitude Sickness | Virus Diseases | Respiratory Insufficiency | Apnea | Depressive Disorder, Major | Pseudohypoparathyroidism | Depressive Disorder | Bronchitis, Chronic | Asthma | Hernias, Diaphragmatic, Congenital | Lung Neoplasms | Severe Acute Respiratory Syndrome | chronic obstructive pulmonary disease | Airway obstruction | chronic kidney disease | acute myeloid leukemia | leukemia | pulmonary arterial hypertension | prostate carcinoma | non-small cell lung carcinoma | kidney disease | altitude sickness | viral disease | respiratory failure | Apnea | major depressive disorder | Albright hereditary osteodystrophy | depressive disorder | chronic bronchitis | asthma | pseudohypoparathyroidism type 1A | pseudohypoparathyroidism | congenital heart disease | lung cancer | COVID-19 | 4.0 | 23 | The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat. | Temple DL, Yevich JP, Catt JD, Owens D, Hanning C, Covington RR, Seidehamel RJ, Dungan KW. | 10.1021/jm00185a008 | null | 1188 | 11 | J Med Chem | null | 6,161,252 | 1 | Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones. | 23 | 1,980 |
null | 35,612 | CHEMBL760588 | Relative inhibition of rat lung phosphodiesterase cGMP and cAMP activity | B | BAO_0000019 | assay format | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O | null | CHEMBL1121553 | J Med Chem | 1,980 | CHEMBL1355736 | THEOPHYLLINE | null | 0 | null | 22,463 | = | 1 | 0 | = | Ratio | null | 2.6 | CHEMBL612545 | null | Unchecked | null | null | Ratio | null | null | 2.6 | null | null | null | null | 1 | 0 | 2 | 1,976 | null | 0 | 4.0 | Protein | 0 | true | true | 0 | THEOPHYLLINE | 0 | MOL | true | false | null | null | false | Cn1c(=O)c2nc[nH]c2n(C)c1=O.O |
RDKit 2D
14 14 0 0 0 0 0 0 0 0999 V2000
8.9134 -7.3176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -6.5370 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -5.2865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.9775 -6.1103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4046 -5.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -6.3752 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.2137 -5.0314 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.6992 -5.6984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -6.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -4.0310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6984 -7.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2419 -4.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 5 1 0
5 2 1 0
6 3 2 0
7 4 1 0
8 3 1 0
9 6 1 0
10 8 1 0
11 5 2 0
12 7 2 0
13 2 1 0
14 4 1 0
6 7 1 0
9 10 2 0
M END
> <chembl_id>
CHEMBL1355736
> <chembl_pref_name>
THEOPHYLLINE | InChI=1S/C7H8N4O2.H2O/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;/h3H,1-2H3,(H,8,9);1H2 | INQSMEFCAIHTJG-UHFFFAOYSA-N | -1.04 | 2 | C7H10N4O3 | 198.18 | 5 | 1 | 13 | 180.17 | -0.75 | 0 | 72.68 | 0.56 | N | 0 | CHEMBL190 | CHEMBL1355736 | CHEMBL190 | Accurbron [TRADE_NAME] | Aerolate [TRADE_NAME] | Aerolate iii [TRADE_NAME] | Aerolate jr [TRADE_NAME] | Aerolate sr [TRADE_NAME] | Aquaphyllin [TRADE_NAME] | Bronkodyl [TRADE_NAME] | Duraphyl [TRADE_NAME] | Elixicon [TRADE_NAME] | Elixomin [TRADE_NAME] | Elixophyllin [TRADE_NAME] | Elixophyllin sr [TRADE_NAME] | Labid [TRADE_NAME] | Lanophyllin [TRADE_NAME] | Lasma [TRADE_NAME] | NSC-757346 [RESEARCH_CODE] | Nuelin [TRADE_NAME] | Nuelin sa [TRADE_NAME] | Nuelin sa-250 [TRADE_NAME] | Pro-vent [TRADE_NAME] | Quibron-t [TRADE_NAME] | Quibron-t/sr [TRADE_NAME] | Slo-bid [TRADE_NAME] | Slo-phyllin [TRADE_NAME] | Somophyllin-crt [TRADE_NAME] | Somophyllin-t [TRADE_NAME] | Sustaire [TRADE_NAME] | Theo-24 [TRADE_NAME] | Theobid [TRADE_NAME] | Theobid jr. [TRADE_NAME] | Theochron [TRADE_NAME] | Theocin [TRADE_NAME] | Theoclear-100 [TRADE_NAME] | Theoclear-200 [TRADE_NAME] | Theoclear-80 [TRADE_NAME] | Theoclear l.a.-130 [TRADE_NAME] | Theoclear l.a.-260 [TRADE_NAME] | Theo-dur [TRADE_NAME] | Theograd [TRADE_NAME] | Theolair [TRADE_NAME] | Theolair-sr [TRADE_NAME] | Theolixir [TRADE_NAME] | Theophyl [TRADE_NAME] | Theophyl-225 [TRADE_NAME] | Theophylline [ATC] | Theophylline [BNF] | Theophylline [FDA] | Theophylline [MERCK_INDEX] | Theophylline [OTHER] | Theophylline [TRADE_NAME] | Theophylline 0.04% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.08% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.16% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.2% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.32% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline 0.4% and dextrose 5% in plastic container [TRADE_NAME] | Theophylline and dextrose 5% in plastic container [TRADE_NAME] | Theophylline component of dicurin procaine [TRADE_NAME] | Theophylline component of mersalyl- [TRADE_NAME] | Theophylline in dextrose 5% in plastic container [TRADE_NAME] | Theophylline monohydrate [OTHER] | Theophylline-sr [TRADE_NAME] | Theophyl-sr [TRADE_NAME] | Theovent [TRADE_NAME] | T-phyl [TRADE_NAME] | Uni-dur [TRADE_NAME] | Uniphyl [TRADE_NAME] | Uniphyllin continus [TRADE_NAME] | DailyMed:theophylline | null | null | Rattus norvegicus | null | null | 10,116 | null | B | Binding | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Relative inhibition of rat lung phosphodiesterase cGMP and cAMP activity | CHEMBL1121553 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | Phosphodiesterase 4 inhibitor | Phosphodiesterase 3 inhibitor | Adenosine receptor antagonist | INHIBITOR | ANTAGONIST | 1 | 1 | null | null | null | Pulmonary Disease, Chronic Obstructive | Lung Diseases, Obstructive | Renal Insufficiency, Chronic | Leukemia, Myeloid, Acute | Leukemia | Hypertension, Pulmonary | Prostatic Neoplasms | Carcinoma, Non-Small-Cell Lung | Kidney Diseases | Altitude Sickness | Virus Diseases | Respiratory Insufficiency | Apnea | Depressive Disorder, Major | Pseudohypoparathyroidism | Depressive Disorder | Bronchitis, Chronic | Asthma | Hernias, Diaphragmatic, Congenital | Lung Neoplasms | Severe Acute Respiratory Syndrome | chronic obstructive pulmonary disease | Airway obstruction | chronic kidney disease | acute myeloid leukemia | leukemia | pulmonary arterial hypertension | prostate carcinoma | non-small cell lung carcinoma | kidney disease | altitude sickness | viral disease | respiratory failure | Apnea | major depressive disorder | Albright hereditary osteodystrophy | depressive disorder | chronic bronchitis | asthma | pseudohypoparathyroidism type 1A | pseudohypoparathyroidism | congenital heart disease | lung cancer | COVID-19 | 4.0 | 23 | The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat. | Temple DL, Yevich JP, Catt JD, Owens D, Hanning C, Covington RR, Seidehamel RJ, Dungan KW. | 10.1021/jm00185a008 | null | 1188 | 11 | J Med Chem | null | 6,161,252 | 1 | Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones. | 23 | 1,980 |
null | 35,613 | CHEMBL775944 | Decrease in mean arterial blood pressure in response to intravenous administration at 2 uM/kg of the compound | F | BAO_0000218 | organism-based format | CN(C)C1=Nc2ccccc2CN1 | null | CHEMBL1121579 | J Med Chem | 1,980 | CHEMBL270409 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 30,838 | = | 1 | 0 | = | Decrease in blood pressure | % | 0 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Decrease in blood pressure | % | UO_0000187 | 0.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)C1=Nc2ccccc2CN1 |
RDKit 2D
13 14 0 0 0 0 0 0 0 0999 V2000
-4.1777 -7.0576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1789 -7.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.4645 -8.2970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.4663 -6.6451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7515 -7.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.7527 -7.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0363 -8.3014 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.3141 -7.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.3129 -7.0560 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.0339 -6.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6013 -8.3027 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.1138 -7.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6036 -9.1272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 6 2 0
1 2 2 0
5 4 2 0
4 1 1 0
5 10 1 0
6 7 1 0
7 8 2 0
8 9 1 0
9 10 1 0
5 6 1 0
8 11 1 0
11 12 1 0
2 3 1 0
11 13 1 0
M END
> <chembl_id>
CHEMBL270409
> <chembl_pref_name>
None | InChI=1S/C10H13N3/c1-13(2)10-11-7-8-5-3-4-6-9(8)12-10/h3-6H,7H2,1-2H3,(H,11,12) | MNTBAXGKERZVOZ-UHFFFAOYSA-N | 1.34 | 1 | C10H13N3 | 175.24 | 3 | 1 | 13 | 175.24 | -0.21 | 0 | 27.63 | 0.64 | Y | 0 | CHEMBL270409 | CHEMBL270409 | CHEMBL270409 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Decrease in mean arterial blood pressure in response to intravenous administration at 2 uM/kg of the compound | CHEMBL1121579 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized. These compounds can be considered to be rigid analogues of phenylguanidines. In anesthetized rats the compounds decreased blood pressure and were antagonists of the pressor response to norepinephrine. | Grosso JA, Nichols DE, Nichols MB, Yim GK. | 10.1021/jm00185a026 | null | 1261 | 11 | J Med Chem | null | 7,452,680 | 1 | Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines. | 23 | 1,980 |
null | 35,614 | CHEMBL775946 | Decrease in mean arterial blood pressure in response to intravenous administration at 4 uM/kg of the compound | F | BAO_0000218 | organism-based format | CN(C)C1=Nc2ccccc2CN1 | null | CHEMBL1121579 | J Med Chem | 1,980 | CHEMBL270409 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 30,838 | = | 1 | 0 | = | Decrease in blood pressure | % | 0 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Decrease in blood pressure | % | UO_0000187 | 0.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)C1=Nc2ccccc2CN1 |
RDKit 2D
13 14 0 0 0 0 0 0 0 0999 V2000
-4.1777 -7.0576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.1789 -7.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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0.1138 -7.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.6036 -9.1272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL270409
> <chembl_pref_name>
None | InChI=1S/C10H13N3/c1-13(2)10-11-7-8-5-3-4-6-9(8)12-10/h3-6H,7H2,1-2H3,(H,11,12) | MNTBAXGKERZVOZ-UHFFFAOYSA-N | 1.34 | 1 | C10H13N3 | 175.24 | 3 | 1 | 13 | 175.24 | -0.21 | 0 | 27.63 | 0.64 | Y | 0 | CHEMBL270409 | CHEMBL270409 | CHEMBL270409 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Decrease in mean arterial blood pressure in response to intravenous administration at 4 uM/kg of the compound | CHEMBL1121579 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized. These compounds can be considered to be rigid analogues of phenylguanidines. In anesthetized rats the compounds decreased blood pressure and were antagonists of the pressor response to norepinephrine. | Grosso JA, Nichols DE, Nichols MB, Yim GK. | 10.1021/jm00185a026 | null | 1261 | 11 | J Med Chem | null | 7,452,680 | 1 | Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines. | 23 | 1,980 |
null | 35,615 | CHEMBL775949 | Decrease in mean arterial blood pressure in response to intravenous administration at 8 uM/kg of the compound | F | BAO_0000218 | organism-based format | CN(C)C1=Nc2ccccc2CN1 | null | CHEMBL1121579 | J Med Chem | 1,980 | CHEMBL270409 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 30,838 | = | 1 | 0 | = | Decrease in blood pressure | % | 5.67 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Decrease in blood pressure | % | UO_0000187 | 5.67 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)C1=Nc2ccccc2CN1 |
RDKit 2D
13 14 0 0 0 0 0 0 0 0999 V2000
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M END
> <chembl_id>
CHEMBL270409
> <chembl_pref_name>
None | InChI=1S/C10H13N3/c1-13(2)10-11-7-8-5-3-4-6-9(8)12-10/h3-6H,7H2,1-2H3,(H,11,12) | MNTBAXGKERZVOZ-UHFFFAOYSA-N | 1.34 | 1 | C10H13N3 | 175.24 | 3 | 1 | 13 | 175.24 | -0.21 | 0 | 27.63 | 0.64 | Y | 0 | CHEMBL270409 | CHEMBL270409 | CHEMBL270409 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Decrease in mean arterial blood pressure in response to intravenous administration at 8 uM/kg of the compound | CHEMBL1121579 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized. These compounds can be considered to be rigid analogues of phenylguanidines. In anesthetized rats the compounds decreased blood pressure and were antagonists of the pressor response to norepinephrine. | Grosso JA, Nichols DE, Nichols MB, Yim GK. | 10.1021/jm00185a026 | null | 1261 | 11 | J Med Chem | null | 7,452,680 | 1 | Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines. | 23 | 1,980 |
null | 35,616 | CHEMBL777707 | Decrease in mean arterial blood pressure in response to intravenous administration at 16 uM/kg of the compound | F | BAO_0000218 | organism-based format | CN(C)C1=Nc2ccccc2CN1 | null | CHEMBL1121579 | J Med Chem | 1,980 | CHEMBL270409 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 30,838 | = | 1 | 0 | = | Decrease in blood pressure | % | 7.3 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Decrease in blood pressure | % | UO_0000187 | 7.3 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)C1=Nc2ccccc2CN1 |
RDKit 2D
13 14 0 0 0 0 0 0 0 0999 V2000
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M END
> <chembl_id>
CHEMBL270409
> <chembl_pref_name>
None | InChI=1S/C10H13N3/c1-13(2)10-11-7-8-5-3-4-6-9(8)12-10/h3-6H,7H2,1-2H3,(H,11,12) | MNTBAXGKERZVOZ-UHFFFAOYSA-N | 1.34 | 1 | C10H13N3 | 175.24 | 3 | 1 | 13 | 175.24 | -0.21 | 0 | 27.63 | 0.64 | Y | 0 | CHEMBL270409 | CHEMBL270409 | CHEMBL270409 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Decrease in mean arterial blood pressure in response to intravenous administration at 16 uM/kg of the compound | CHEMBL1121579 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized. These compounds can be considered to be rigid analogues of phenylguanidines. In anesthetized rats the compounds decreased blood pressure and were antagonists of the pressor response to norepinephrine. | Grosso JA, Nichols DE, Nichols MB, Yim GK. | 10.1021/jm00185a026 | null | 1261 | 11 | J Med Chem | null | 7,452,680 | 1 | Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines. | 23 | 1,980 |
null | 35,617 | CHEMBL882050 | Decrease in mean arterial blood pressure in response to intravenous administration at 32 uM/kg of the compound | F | BAO_0000218 | organism-based format | CN(C)C1=Nc2ccccc2CN1 | null | CHEMBL1121579 | J Med Chem | 1,980 | CHEMBL270409 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 30,838 | = | 1 | 0 | = | Decrease in blood pressure | % | 12.3 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Decrease in blood pressure | % | UO_0000187 | 12.3 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)C1=Nc2ccccc2CN1 |
RDKit 2D
13 14 0 0 0 0 0 0 0 0999 V2000
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M END
> <chembl_id>
CHEMBL270409
> <chembl_pref_name>
None | InChI=1S/C10H13N3/c1-13(2)10-11-7-8-5-3-4-6-9(8)12-10/h3-6H,7H2,1-2H3,(H,11,12) | MNTBAXGKERZVOZ-UHFFFAOYSA-N | 1.34 | 1 | C10H13N3 | 175.24 | 3 | 1 | 13 | 175.24 | -0.21 | 0 | 27.63 | 0.64 | Y | 0 | CHEMBL270409 | CHEMBL270409 | CHEMBL270409 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Decrease in mean arterial blood pressure in response to intravenous administration at 32 uM/kg of the compound | CHEMBL1121579 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized. These compounds can be considered to be rigid analogues of phenylguanidines. In anesthetized rats the compounds decreased blood pressure and were antagonists of the pressor response to norepinephrine. | Grosso JA, Nichols DE, Nichols MB, Yim GK. | 10.1021/jm00185a026 | null | 1261 | 11 | J Med Chem | null | 7,452,680 | 1 | Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines. | 23 | 1,980 |
null | 35,618 | CHEMBL775948 | Decrease in mean arterial blood pressure in response to intravenous administration at 64 uM/kg of the compound. | F | BAO_0000218 | organism-based format | CN(C)C1=Nc2ccccc2CN1 | null | CHEMBL1121579 | J Med Chem | 1,980 | CHEMBL270409 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 30,838 | = | 1 | 0 | = | Decrease in blood pressure | % | 24.7 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Decrease in blood pressure | % | UO_0000187 | 24.7 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)C1=Nc2ccccc2CN1 |
RDKit 2D
13 14 0 0 0 0 0 0 0 0999 V2000
-4.1777 -7.0576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL270409
> <chembl_pref_name>
None | InChI=1S/C10H13N3/c1-13(2)10-11-7-8-5-3-4-6-9(8)12-10/h3-6H,7H2,1-2H3,(H,11,12) | MNTBAXGKERZVOZ-UHFFFAOYSA-N | 1.34 | 1 | C10H13N3 | 175.24 | 3 | 1 | 13 | 175.24 | -0.21 | 0 | 27.63 | 0.64 | Y | 0 | CHEMBL270409 | CHEMBL270409 | CHEMBL270409 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Decrease in mean arterial blood pressure in response to intravenous administration at 64 uM/kg of the compound. | CHEMBL1121579 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized. These compounds can be considered to be rigid analogues of phenylguanidines. In anesthetized rats the compounds decreased blood pressure and were antagonists of the pressor response to norepinephrine. | Grosso JA, Nichols DE, Nichols MB, Yim GK. | 10.1021/jm00185a026 | null | 1261 | 11 | J Med Chem | null | 7,452,680 | 1 | Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines. | 23 | 1,980 |
null | 35,619 | CHEMBL774154 | Antagonist effect to pressor response of 0.3 ug/kg of norepinephrine intravenously in rats at the dose 32 uM/kg | F | BAO_0000218 | organism-based format | CN(C)C1=Nc2ccccc2CN1 | null | CHEMBL1121579 | J Med Chem | 1,980 | CHEMBL270409 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 30,838 | = | 1 | 0 | = | Block | % | 10 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Block | % | UO_0000187 | 10.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)C1=Nc2ccccc2CN1 |
RDKit 2D
13 14 0 0 0 0 0 0 0 0999 V2000
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M END
> <chembl_id>
CHEMBL270409
> <chembl_pref_name>
None | InChI=1S/C10H13N3/c1-13(2)10-11-7-8-5-3-4-6-9(8)12-10/h3-6H,7H2,1-2H3,(H,11,12) | MNTBAXGKERZVOZ-UHFFFAOYSA-N | 1.34 | 1 | C10H13N3 | 175.24 | 3 | 1 | 13 | 175.24 | -0.21 | 0 | 27.63 | 0.64 | Y | 0 | CHEMBL270409 | CHEMBL270409 | CHEMBL270409 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Antagonist effect to pressor response of 0.3 ug/kg of norepinephrine intravenously in rats at the dose 32 uM/kg | CHEMBL1121579 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Based on the known biological activity of a variety of guanidine-containing agents, several N-substituted 3,4-dihydroquinazolines were synthesized. These compounds can be considered to be rigid analogues of phenylguanidines. In anesthetized rats the compounds decreased blood pressure and were antagonists of the pressor response to norepinephrine. | Grosso JA, Nichols DE, Nichols MB, Yim GK. | 10.1021/jm00185a026 | null | 1261 | 11 | J Med Chem | null | 7,452,680 | 1 | Synthesis and adrenergic blocking effects of 2-(alkylamino)-3,4-dihydroquinazolines. | 23 | 1,980 |
null | 35,620 | CHEMBL773605 | Lowest active dose which cured rats with Entamoeba histolytica cecal infection was measured | F | BAO_0000218 | organism-based format | CN1CCN(c2nc3ccc(N)cc3nc2N2CCN(C)CC2)CC1 | null | CHEMBL1121391 | J Med Chem | 1,980 | CHEMBL417733 | null | null | 0 | null | 110,548 | = | 1 | 0 | = | Dose | mg kg-1 day-1 | 50 | CHEMBL612853 | Entamoeba histolytica | Entamoeba histolytica | 5759 | null | Dose | mg kg-1 day-1 | UO_0000311 | 50.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN1CCN(c2nc3ccc(N)cc3nc2N2CCN(C)CC2)CC1 |
RDKit 2D
25 28 0 0 0 0 0 0 0 0999 V2000
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18 10 1 0
4 8 1 0
9 21 1 0
23 16 1 0
M END
> <chembl_id>
CHEMBL417733
> <chembl_pref_name>
None | InChI=1S/C18H27N7/c1-22-5-9-24(10-6-22)17-18(25-11-7-23(2)8-12-25)21-16-13-14(19)3-4-15(16)20-17/h3-4,13H,5-12,19H2,1-2H3 | DYJCLTDKKIKWJG-UHFFFAOYSA-N | 0.72 | 2 | C18H27N7 | 341.46 | 7 | 1 | 25 | 341.46 | -0.89 | 0 | 64.76 | 0.81 | N | 2 | CHEMBL417733 | CHEMBL417733 | CHEMBL417733 | null | null | null | null | Entamoeba histolytica | null | null | 5,759 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Lowest active dose which cured rats with Entamoeba histolytica cecal infection was measured | CHEMBL1121391 | Non-molecular target assigned | N | null | 1 | CHEMBL612853 | null | null | null | Entamoeba histolytica | Entamoeba histolytica | false | ORGANISM | 5,759 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of amidines and sulfonamides of 5- and 6-amino-2,3-bis(4-alkyl-1-piperazinyl)quinoxalines was synthesized and tested against cecal and hepatic forms of Entamoeba histolytica infections in rats and hamsters, respectively. Four compounds (5, 6, 8, and 9) were found to have acceptable activity against infections in both species but were too toxic to be considered for use in man. | Fabio PF, Lang SA, Lin YI, Tomcufcik AS. | 10.1021/jm00176a017 | null | 201 | 2 | J Med Chem | null | 7,359,534 | 1 | Antiamebic amidines and sulfonamides of 5- and 6-amino-2,3-bis(4-alkyl-1-piperazinyl)quinoxalines. | 23 | 1,980 |
null | 35,622 | CHEMBL778496 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 40 mg/kg in conscious renal hypertensive rats (RHR). | F | BAO_0000218 | organism-based format | Cc1cccc(NC(=O)NC2CCN(CCc3c[nH]c4ccccc34)CC2)c1 | null | CHEMBL1121617 | J Med Chem | 1,980 | CHEMBL169389 | null | null | 0 | null | 334,455 | = | 1 | 0 | = | Activity | null | 14 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Activity | null | null | 14.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Cc1cccc(NC(=O)NC2CCN(CCc3c[nH]c4ccccc34)CC2)c1 |
RDKit 2D
28 31 0 0 0 0 0 0 0 0999 V2000
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M END
> <chembl_id>
CHEMBL169389
> <chembl_pref_name>
None | InChI=1S/C23H28N4O/c1-17-5-4-6-20(15-17)26-23(28)25-19-10-13-27(14-11-19)12-9-18-16-24-22-8-3-2-7-21(18)22/h2-8,15-16,19,24H,9-14H2,1H3,(H2,25,26,28) | WXBRFAULXRFZPT-UHFFFAOYSA-N | 4.3 | 3 | C23H28N4O | 376.50 | 2 | 3 | 28 | 376.5 | -1.53 | 0 | 60.16 | 0.62 | N | 5 | CHEMBL169389 | CHEMBL169389 | CHEMBL169389 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 40 mg/kg in conscious renal hypertensive rats (RHR). | CHEMBL1121617 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | DOSE=40.0 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series. | Archibald JL, Beardsley DR, Bisset GM, Fairbrother P, Jackson JL, Opalko A, Ward TJ. | 10.1021/jm00182a009 | null | 857 | 8 | J Med Chem | null | 7,401,114 | 1 | Antihypertensive ureidopiperidines. | 23 | 1,980 |
null | 35,623 | CHEMBL792281 | Starting systolic blood pressure at dose of 50 mg/kg in rat | F | BAO_0000218 | organism-based format | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 | null | CHEMBL1121617 | J Med Chem | 1,980 | CHEMBL353005 | null | null | 0 | null | 334,496 | = | 1 | 0 | = | SP | mmHg | 179 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | SP | mmHg | UO_0000272 | 179.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 |
RDKit 2D
29 31 0 0 0 0 0 0 0 0999 V2000
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6.4875 -2.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL353005
> <chembl_pref_name>
None | InChI=1S/C21H24FN3O3S/c22-16-7-5-15(6-8-16)18(26)3-1-11-25-12-9-17(10-13-25)23-21(28)24-20(27)19-4-2-14-29-19/h2,4-8,14,17H,1,3,9-13H2,(H2,23,24,27,28) | NSMREXXYHJWAAO-UHFFFAOYSA-N | 3.45 | 2 | C21H24FN3O3S | 417.51 | 5 | 2 | 29 | 417.51 | -1.99 | 0 | 78.51 | 0.68 | N | 7 | CHEMBL353005 | CHEMBL353005 | CHEMBL353005 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Starting systolic blood pressure at dose of 50 mg/kg in rat | CHEMBL1121617 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | DOSE=50.0 mg/kg | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series. | Archibald JL, Beardsley DR, Bisset GM, Fairbrother P, Jackson JL, Opalko A, Ward TJ. | 10.1021/jm00182a009 | null | 857 | 8 | J Med Chem | null | 7,401,114 | 1 | Antihypertensive ureidopiperidines. | 23 | 1,980 |
null | 35,624 | CHEMBL782993 | The percent fall in systolic blood pressure at 1.5 / 4 h after peroral administration of 50 mg/kg in DOCA/saline hypertensive rats at 2 hr | F | BAO_0000218 | organism-based format | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 | null | CHEMBL1121617 | J Med Chem | 1,980 | CHEMBL353005 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 334,496 | = | 1 | 0 | = | Fall | % | 49 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Fall | % | UO_0000187 | 49.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 |
RDKit 2D
29 31 0 0 0 0 0 0 0 0999 V2000
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5.6417 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL353005
> <chembl_pref_name>
None | InChI=1S/C21H24FN3O3S/c22-16-7-5-15(6-8-16)18(26)3-1-11-25-12-9-17(10-13-25)23-21(28)24-20(27)19-4-2-14-29-19/h2,4-8,14,17H,1,3,9-13H2,(H2,23,24,27,28) | NSMREXXYHJWAAO-UHFFFAOYSA-N | 3.45 | 2 | C21H24FN3O3S | 417.51 | 5 | 2 | 29 | 417.51 | -1.99 | 0 | 78.51 | 0.68 | N | 7 | CHEMBL353005 | CHEMBL353005 | CHEMBL353005 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | The percent fall in systolic blood pressure at 1.5 / 4 h after peroral administration of 50 mg/kg in DOCA/saline hypertensive rats at 2 hr | CHEMBL1121617 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | DOSE=50.0 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series. | Archibald JL, Beardsley DR, Bisset GM, Fairbrother P, Jackson JL, Opalko A, Ward TJ. | 10.1021/jm00182a009 | null | 857 | 8 | J Med Chem | null | 7,401,114 | 1 | Antihypertensive ureidopiperidines. | 23 | 1,980 |
null | 35,625 | CHEMBL787703 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 50 mg/kg in DOCA/saline hypertensive rats at 6 hr | F | BAO_0000218 | organism-based format | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 | null | CHEMBL1121617 | J Med Chem | 1,980 | CHEMBL353005 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 334,496 | = | 1 | 0 | = | Fall | % | 45 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Fall | % | UO_0000187 | 45.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 |
RDKit 2D
29 31 0 0 0 0 0 0 0 0999 V2000
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5.6417 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4875 -2.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL353005
> <chembl_pref_name>
None | InChI=1S/C21H24FN3O3S/c22-16-7-5-15(6-8-16)18(26)3-1-11-25-12-9-17(10-13-25)23-21(28)24-20(27)19-4-2-14-29-19/h2,4-8,14,17H,1,3,9-13H2,(H2,23,24,27,28) | NSMREXXYHJWAAO-UHFFFAOYSA-N | 3.45 | 2 | C21H24FN3O3S | 417.51 | 5 | 2 | 29 | 417.51 | -1.99 | 0 | 78.51 | 0.68 | N | 7 | CHEMBL353005 | CHEMBL353005 | CHEMBL353005 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 50 mg/kg in DOCA/saline hypertensive rats at 6 hr | CHEMBL1121617 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | DOSE=50.0 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series. | Archibald JL, Beardsley DR, Bisset GM, Fairbrother P, Jackson JL, Opalko A, Ward TJ. | 10.1021/jm00182a009 | null | 857 | 8 | J Med Chem | null | 7,401,114 | 1 | Antihypertensive ureidopiperidines. | 23 | 1,980 |
null | 35,626 | CHEMBL782991 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 50 mg/kg in DOCA/saline hypertensive rats at 24 hr | F | BAO_0000218 | organism-based format | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 | null | CHEMBL1121617 | J Med Chem | 1,980 | CHEMBL353005 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 334,496 | = | 1 | 0 | = | Fall | % | 21 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Fall | % | UO_0000187 | 21.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 |
RDKit 2D
29 31 0 0 0 0 0 0 0 0999 V2000
6.2417 -1.5125 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.6417 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4875 -2.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.0792 -2.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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5.4000 -0.9000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
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3.0042 -0.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.6500 -1.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2 1 1 0
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23 25 1 0
M END
> <chembl_id>
CHEMBL353005
> <chembl_pref_name>
None | InChI=1S/C21H24FN3O3S/c22-16-7-5-15(6-8-16)18(26)3-1-11-25-12-9-17(10-13-25)23-21(28)24-20(27)19-4-2-14-29-19/h2,4-8,14,17H,1,3,9-13H2,(H2,23,24,27,28) | NSMREXXYHJWAAO-UHFFFAOYSA-N | 3.45 | 2 | C21H24FN3O3S | 417.51 | 5 | 2 | 29 | 417.51 | -1.99 | 0 | 78.51 | 0.68 | N | 7 | CHEMBL353005 | CHEMBL353005 | CHEMBL353005 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | The percent fall in systolic blood pressure at 1.5 / 4 hr after peroral administration of 50 mg/kg in DOCA/saline hypertensive rats at 24 hr | CHEMBL1121617 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | DOSE=50.0 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series. | Archibald JL, Beardsley DR, Bisset GM, Fairbrother P, Jackson JL, Opalko A, Ward TJ. | 10.1021/jm00182a009 | null | 857 | 8 | J Med Chem | null | 7,401,114 | 1 | Antihypertensive ureidopiperidines. | 23 | 1,980 |
null | 35,627 | CHEMBL792280 | Starting systolic blood pressure at dose of 25 mg/kg | F | BAO_0000218 | organism-based format | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 | null | CHEMBL1121617 | J Med Chem | 1,980 | CHEMBL353005 | null | null | 0 | null | 334,496 | = | 1 | 0 | = | SP | mmHg | 174 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | SP | mmHg | UO_0000272 | 174.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(NC(=O)c1cccs1)NC1CCN(CCCC(=O)c2ccc(F)cc2)CC1 |
RDKit 2D
29 31 0 0 0 0 0 0 0 0999 V2000
6.2417 -1.5125 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.6417 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.4875 -2.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.0792 -2.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.5292 -1.7125 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
3.6042 -0.7167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4000 -0.9000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.6875 -1.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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7.9417 -2.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0917 -1.4917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.5167 -2.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5667 -2.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4417 -1.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5542 -0.2875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.7917 -0.8375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8417 -1.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9542 -0.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4000 -3.2167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8042 -3.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.7625 -2.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -3.7917 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
3.0042 -0.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.6500 -1.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0500 -1.0750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 1 1 0
4 3 1 0
5 4 1 0
6 22 1 0
7 2 1 0
8 29 1 0
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29 28 1 0
13 14 2 0
6 21 1 0
23 25 1 0
M END
> <chembl_id>
CHEMBL353005
> <chembl_pref_name>
None | InChI=1S/C21H24FN3O3S/c22-16-7-5-15(6-8-16)18(26)3-1-11-25-12-9-17(10-13-25)23-21(28)24-20(27)19-4-2-14-29-19/h2,4-8,14,17H,1,3,9-13H2,(H2,23,24,27,28) | NSMREXXYHJWAAO-UHFFFAOYSA-N | 3.45 | 2 | C21H24FN3O3S | 417.51 | 5 | 2 | 29 | 417.51 | -1.99 | 0 | 78.51 | 0.68 | N | 7 | CHEMBL353005 | CHEMBL353005 | CHEMBL353005 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Artery | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Starting systolic blood pressure at dose of 25 mg/kg | CHEMBL1121617 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638216 | null | DOSE=25.0 mg/kg | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series. | Archibald JL, Beardsley DR, Bisset GM, Fairbrother P, Jackson JL, Opalko A, Ward TJ. | 10.1021/jm00182a009 | null | 857 | 8 | J Med Chem | null | 7,401,114 | 1 | Antihypertensive ureidopiperidines. | 23 | 1,980 |
null | 33,154 | CHEMBL663829 | Saluretic property was estimated by the excretion of Na+ in dog administered intravenously; microequiv of Na+/min at 5 mg/kg iv stat, 0-99 | A | BAO_0000218 | organism-based format | CN(C)Cc1cc(C(C)(C)C)cc(I)c1O | null | CHEMBL1122081 | J Med Chem | 1,982 | CHEMBL163066 | null | null | 0 | null | 321,226 | = | 1 | 0 | = | Saluretic potency | u equiv min-1 | 0 | CHEMBL373 | Canis lupus familiaris | Canis familiaris | 9615 | null | Saluretic potency | u equiv min-1 | null | 0.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CN(C)Cc1cc(C(C)(C)C)cc(I)c1O |
RDKit 2D
16 16 0 0 0 0 0 0 0 0999 V2000
3.5542 -1.3375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0292 -2.2417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0292 -1.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5167 -1.3375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -1.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5167 -1.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0667 -1.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0292 -2.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0667 -0.4292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.9917 -1.0417 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0
3.0292 -0.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -3.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0292 -3.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5167 -3.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.5792 -0.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5417 -0.1375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 5 2 0
3 1 2 0
4 3 1 0
5 1 1 0
6 2 1 0
7 1 1 0
8 2 1 0
9 7 1 0
10 4 1 0
11 3 1 0
12 8 1 0
13 8 1 0
14 8 1 0
15 9 1 0
16 9 1 0
4 6 2 0
M END
> <chembl_id>
CHEMBL163066
> <chembl_pref_name>
None | InChI=1S/C13H20INO/c1-13(2,3)10-6-9(8-15(4)5)12(16)11(14)7-10/h6-7,16H,8H2,1-5H3 | XCTGWUBSZMSEJY-UHFFFAOYSA-N | 3.36 | 1 | C13H20INO | 333.21 | 2 | 1 | 16 | 333.21 | -0.75 | 0 | 23.47 | 0.84 | N | 2 | CHEMBL163066 | CHEMBL163066 | CHEMBL163066 | null | null | null | null | Canis lupus familiaris | null | null | 9,615 | null | A | ADME | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Saluretic property was estimated by the excretion of Na+ in dog administered intravenously; microequiv of Na+/min at 5 mg/kg iv stat, 0-99 | CHEMBL1122081 | Non-molecular target assigned | N | null | 1 | CHEMBL373 | null | null | DOSE=5.0 mg/kg | ROUTE=None None | Canis lupus familiaris | Canis familiaris | false | ORGANISM | 9,615 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of oxygen and/or nitrogen substituted 2-(aminomethyl)phenols was synthesized and tested orally in rats for saluretic and diuretic effects. Intravenous dog data are included as supplementary material to demonstrate diuretic responses, or lack thereof, in a second species. In general, substitution on nitrogen with groups other than lower alkyl or substitution on nitrogen and/or oxygen with groups resistant to hydrolysis substantially diminished or ablated saluretic effects. | Stokker GE, Deana AA, deSolms SJ, Schultz EM, Smith RL, Cragoe EJ, Baer JE, Russo HF, Watson LS. | 10.1021/jm00348a024 | null | 735 | 6 | J Med Chem | null | 7,097,728 | 1 | 2-(Aminomethyl)phenols, a new class of saluretic agents. 4. Effects of oxygen and/or nitrogen substitution. | 25 | 1,982 |
null | 33,156 | CHEMBL788494 | Percent inhibition of rat passive cutaneous anaphylaxis model after intravenous administration of the 0.5 mg/kg | F | BAO_0000218 | organism-based format | O=c1c2ccccc2nc2ccc(-c3nn[nH]n3)cn12 | null | CHEMBL1122082 | J Med Chem | 1,982 | CHEMBL163354 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 321,565 | = | 1 | 1 | = | Inhibition | % | 68 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Inhibition | % | UO_0000187 | 68.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=c1c2ccccc2nc2ccc(-c3nn[nH]n3)cn12 |
RDKit 2D
20 23 0 0 0 0 0 0 0 0999 V2000
1.2667 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.7417 -1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.3042 -0.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7792 -1.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7417 0.1458 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.8250 -1.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2250 -0.7542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3625 -0.7792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.7750 -1.2167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.9125 -1.6417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.5000 -1.7417 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.2250 -0.1542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3042 -0.1542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7792 0.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7375 -1.6542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.2958 -1.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.2958 0.1458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.8208 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2 1 1 0
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15 3 1 0
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17 8 2 0
18 13 2 0
19 17 1 0
20 18 1 0
15 14 2 0
13 8 1 0
12 10 1 0
19 20 2 0
M END
> <chembl_id>
CHEMBL163354
> <chembl_pref_name>
None | InChI=1S/C13H8N6O/c20-13-9-3-1-2-4-10(9)14-11-6-5-8(7-19(11)13)12-15-17-18-16-12/h1-7H,(H,15,16,17,18) | VDTILFANVMDZEW-UHFFFAOYSA-N | 1.03 | 4 | C13H8N6O | 264.25 | 6 | 1 | 20 | 264.25 | -1.78 | 0 | 88.83 | 0.52 | N | 1 | CHEMBL163354 | CHEMBL163354 | CHEMBL163354 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Percent inhibition of rat passive cutaneous anaphylaxis model after intravenous administration of the 0.5 mg/kg | CHEMBL1122082 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | DOSE=0.5 mg/kg | ROUTE=None None | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Several known antiallergic agents, including cromolyn sodium and a series of pyrido[2,1-b]quinazolines, inhibit human alkaline phosphatase (ALP), a membranal enzyme associated with calcium uptake in certain tissues. A comparison of ALP and rat passive cutaneous anaphylaxis (PCA) inhibition indicates that PCA inhibition may be associated with drug-ALP interaction, since ALP inhibition potency parallels PCA inhibitory activity. The unpredictability of the PCA test toward clinical efficacy could in part be related to the uncompetitive nature of these inhibitors. The results also suggest that alkaline phosphatase may be a component of membranal calcium channels. | Schwender CF, Sunday BR, Decker VL. | 10.1021/jm00348a025 | null | 742 | 6 | J Med Chem | null | 6,808,133 | 1 | Alkaline phosphatase inhibition by a series of pyrido[2,1-b]quinazolines: A possible relationship with cromolyn-like antiallergy activity. | 25 | 1,982 |
null | 33,159 | CHEMBL634600 | Solubility ratio ([HbS+drug (5 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL368988 | null | null | 0 | null | 347,488 | = | 1 | 0 | = | Solubility ratio | null | 1.057 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.057 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
3.3792 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2042 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9625 -0.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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2.9750 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5708 -2.1792 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
-0.3333 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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7 2 1 0
8 13 1 0
9 16 1 0
10 1 1 0
11 8 1 0
12 14 1 0
13 15 2 0
14 9 2 0
15 9 1 0
16 17 1 0
17 10 1 0
8 12 2 0
M END
> <chembl_id>
CHEMBL368988
> <chembl_pref_name>
None | InChI=1S/C11H11BrO5/c12-7-1-3-8(4-2-7)17-6-5-9(10(13)14)11(15)16/h1-4,9H,5-6H2,(H,13,14)(H,15,16) | WKNLVAFBHNNWQX-UHFFFAOYSA-N | 2 | 1 | C11H11BrO5 | 303.11 | 3 | 2 | 17 | 303.11 | -0.24 | 0 | 83.83 | 0.79 | N | 6 | CHEMBL368988 | CHEMBL368988 | CHEMBL368988 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (5 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,160 | CHEMBL633104 | Solubility ratio ([HbS+drug (10 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL368988 | null | null | 0 | null | 347,488 | = | 1 | 0 | = | Solubility ratio | null | 1.134 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.134 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
3.3792 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2042 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9625 -0.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -0.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6292 -1.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.3750 0.7125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6167 0.0083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.7458 -2.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.9042 -2.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9750 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5708 -2.1792 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
-0.3333 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3250 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4875 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5042 -2.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7375 -2.1667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.1500 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 1 1 0
4 3 2 0
5 2 2 0
6 3 1 0
7 2 1 0
8 13 1 0
9 16 1 0
10 1 1 0
11 8 1 0
12 14 1 0
13 15 2 0
14 9 2 0
15 9 1 0
16 17 1 0
17 10 1 0
8 12 2 0
M END
> <chembl_id>
CHEMBL368988
> <chembl_pref_name>
None | InChI=1S/C11H11BrO5/c12-7-1-3-8(4-2-7)17-6-5-9(10(13)14)11(15)16/h1-4,9H,5-6H2,(H,13,14)(H,15,16) | WKNLVAFBHNNWQX-UHFFFAOYSA-N | 2 | 1 | C11H11BrO5 | 303.11 | 3 | 2 | 17 | 303.11 | -0.24 | 0 | 83.83 | 0.79 | N | 6 | CHEMBL368988 | CHEMBL368988 | CHEMBL368988 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (10 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,161 | CHEMBL633105 | Solubility ratio ([HbS+drug (20 mM)]/[HbS-drug] | A | BAO_0000019 | assay format | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL368988 | null | null | 0 | null | 347,488 | = | 1 | 0 | = | Solubility ratio | null | 1.323 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.323 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
3.3792 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2042 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9625 -0.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -0.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6292 -1.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.3750 0.7125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6167 0.0083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.7458 -2.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.9042 -2.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9750 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5708 -2.1792 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
-0.3333 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3250 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4875 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5042 -2.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7375 -2.1667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.1500 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 1 1 0
4 3 2 0
5 2 2 0
6 3 1 0
7 2 1 0
8 13 1 0
9 16 1 0
10 1 1 0
11 8 1 0
12 14 1 0
13 15 2 0
14 9 2 0
15 9 1 0
16 17 1 0
17 10 1 0
8 12 2 0
M END
> <chembl_id>
CHEMBL368988
> <chembl_pref_name>
None | InChI=1S/C11H11BrO5/c12-7-1-3-8(4-2-7)17-6-5-9(10(13)14)11(15)16/h1-4,9H,5-6H2,(H,13,14)(H,15,16) | WKNLVAFBHNNWQX-UHFFFAOYSA-N | 2 | 1 | C11H11BrO5 | 303.11 | 3 | 2 | 17 | 303.11 | -0.24 | 0 | 83.83 | 0.79 | N | 6 | CHEMBL368988 | CHEMBL368988 | CHEMBL368988 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (20 mM)]/[HbS-drug] | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,162 | CHEMBL634599 | Solubility ratio ([HbS+drug (40 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL368988 | null | null | 0 | null | 347,488 | = | 1 | 0 | = | Solubility ratio | null | 1.36 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.36 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)C(CCOc1ccc(Br)cc1)C(=O)O |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
3.3792 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2042 -0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9625 -0.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1417 -0.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6292 -1.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.3750 0.7125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.6167 0.0083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.7458 -2.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.9042 -2.1667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9750 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5708 -2.1792 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
-0.3333 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3250 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.4875 -1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.5042 -2.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7375 -2.1667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.1500 -1.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 1 1 0
4 3 2 0
5 2 2 0
6 3 1 0
7 2 1 0
8 13 1 0
9 16 1 0
10 1 1 0
11 8 1 0
12 14 1 0
13 15 2 0
14 9 2 0
15 9 1 0
16 17 1 0
17 10 1 0
8 12 2 0
M END
> <chembl_id>
CHEMBL368988
> <chembl_pref_name>
None | InChI=1S/C11H11BrO5/c12-7-1-3-8(4-2-7)17-6-5-9(10(13)14)11(15)16/h1-4,9H,5-6H2,(H,13,14)(H,15,16) | WKNLVAFBHNNWQX-UHFFFAOYSA-N | 2 | 1 | C11H11BrO5 | 303.11 | 3 | 2 | 17 | 303.11 | -0.24 | 0 | 83.83 | 0.79 | N | 6 | CHEMBL368988 | CHEMBL368988 | CHEMBL368988 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (40 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,165 | CHEMBL634600 | Solubility ratio ([HbS+drug (5 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | O=C(O)COCc1ccc(Br)cc1 | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL9256 | null | null | 0 | null | 347,497 | = | 1 | 0 | = | Solubility ratio | null | 1.059 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.059 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)COCc1ccc(Br)cc1 |
RDKit 2D
13 13 0 0 0 0 0 0 0 0999 V2000
6.1792 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.8167 -0.9292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.2500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3542 -2.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.7792 -1.3375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.4500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4625 -1.5292 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5417 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.9417 -1.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0500 -1.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 9 1 0
4 12 1 0
5 1 1 0
6 13 1 0
7 3 1 0
8 10 1 0
9 11 2 0
10 6 2 0
11 6 1 0
12 1 1 0
13 4 1 0
3 8 2 0
M END
> <chembl_id>
CHEMBL9256
> <chembl_pref_name>
None | InChI=1S/C9H9BrO3/c10-8-3-1-7(2-4-8)5-13-6-9(11)12/h1-4H,5-6H2,(H,11,12) | ZIEXYIQTFZVRBI-UHFFFAOYSA-N | 2.05 | 1 | C9H9BrO3 | 245.07 | 2 | 1 | 13 | 245.07 | -0.62 | 0 | 46.53 | 0.88 | N | 4 | CHEMBL9256 | CHEMBL9256 | CHEMBL9256 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (5 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,166 | CHEMBL633104 | Solubility ratio ([HbS+drug (10 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | O=C(O)COCc1ccc(Br)cc1 | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL9256 | null | null | 0 | null | 347,497 | = | 1 | 0 | = | Solubility ratio | null | 1.118 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.118 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)COCc1ccc(Br)cc1 |
RDKit 2D
13 13 0 0 0 0 0 0 0 0999 V2000
6.1792 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.8167 -0.9292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.2500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3542 -2.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.7792 -1.3375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.4500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4625 -1.5292 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5417 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.9417 -1.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0500 -1.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 9 1 0
4 12 1 0
5 1 1 0
6 13 1 0
7 3 1 0
8 10 1 0
9 11 2 0
10 6 2 0
11 6 1 0
12 1 1 0
13 4 1 0
3 8 2 0
M END
> <chembl_id>
CHEMBL9256
> <chembl_pref_name>
None | InChI=1S/C9H9BrO3/c10-8-3-1-7(2-4-8)5-13-6-9(11)12/h1-4H,5-6H2,(H,11,12) | ZIEXYIQTFZVRBI-UHFFFAOYSA-N | 2.05 | 1 | C9H9BrO3 | 245.07 | 2 | 1 | 13 | 245.07 | -0.62 | 0 | 46.53 | 0.88 | N | 4 | CHEMBL9256 | CHEMBL9256 | CHEMBL9256 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (10 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,167 | CHEMBL633105 | Solubility ratio ([HbS+drug (20 mM)]/[HbS-drug] | A | BAO_0000019 | assay format | O=C(O)COCc1ccc(Br)cc1 | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL9256 | null | null | 0 | null | 347,497 | = | 1 | 0 | = | Solubility ratio | null | 1.233 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.233 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)COCc1ccc(Br)cc1 |
RDKit 2D
13 13 0 0 0 0 0 0 0 0999 V2000
6.1792 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.8167 -0.9292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.2500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3542 -2.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.7792 -1.3375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.4500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4625 -1.5292 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5417 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.9417 -1.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0500 -1.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 9 1 0
4 12 1 0
5 1 1 0
6 13 1 0
7 3 1 0
8 10 1 0
9 11 2 0
10 6 2 0
11 6 1 0
12 1 1 0
13 4 1 0
3 8 2 0
M END
> <chembl_id>
CHEMBL9256
> <chembl_pref_name>
None | InChI=1S/C9H9BrO3/c10-8-3-1-7(2-4-8)5-13-6-9(11)12/h1-4H,5-6H2,(H,11,12) | ZIEXYIQTFZVRBI-UHFFFAOYSA-N | 2.05 | 1 | C9H9BrO3 | 245.07 | 2 | 1 | 13 | 245.07 | -0.62 | 0 | 46.53 | 0.88 | N | 4 | CHEMBL9256 | CHEMBL9256 | CHEMBL9256 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (20 mM)]/[HbS-drug] | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,168 | CHEMBL634599 | Solubility ratio ([HbS+drug (40 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | O=C(O)COCc1ccc(Br)cc1 | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL9256 | null | null | 0 | null | 347,497 | = | 1 | 0 | = | Solubility ratio | null | 1.398 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.398 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | O=C(O)COCc1ccc(Br)cc1 |
RDKit 2D
13 13 0 0 0 0 0 0 0 0999 V2000
6.1792 -1.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.8167 -0.9292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.2500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.3542 -2.0292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
6.7792 -1.3375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.4500 -1.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4625 -1.5292 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5417 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1500 -2.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.9417 -1.9625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0500 -1.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 9 1 0
4 12 1 0
5 1 1 0
6 13 1 0
7 3 1 0
8 10 1 0
9 11 2 0
10 6 2 0
11 6 1 0
12 1 1 0
13 4 1 0
3 8 2 0
M END
> <chembl_id>
CHEMBL9256
> <chembl_pref_name>
None | InChI=1S/C9H9BrO3/c10-8-3-1-7(2-4-8)5-13-6-9(11)12/h1-4H,5-6H2,(H,11,12) | ZIEXYIQTFZVRBI-UHFFFAOYSA-N | 2.05 | 1 | C9H9BrO3 | 245.07 | 2 | 1 | 13 | 245.07 | -0.62 | 0 | 46.53 | 0.88 | N | 4 | CHEMBL9256 | CHEMBL9256 | CHEMBL9256 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (40 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,171 | CHEMBL634600 | Solubility ratio ([HbS+drug (5 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | COc1cc(OCC(=O)O)cc(OC)c1OC | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL176835 | null | null | 0 | null | 347,503 | = | 1 | 0 | = | Solubility ratio | null | 0.987 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 0.987 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | COc1cc(OCC(=O)O)cc(OC)c1OC |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
2.0917 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -2.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -3.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.0792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -1.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -3.8042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -4.6167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6750 -1.3167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.6417 -3.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6542 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -5.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 1 1 0
4 3 2 0
5 2 1 0
6 4 1 0
7 10 1 0
8 7 2 0
9 6 1 0
10 9 1 0
11 1 1 0
12 2 1 0
13 3 1 0
14 7 1 0
15 11 1 0
16 12 1 0
17 13 1 0
6 5 2 0
M END
> <chembl_id>
CHEMBL176835
> <chembl_pref_name>
None | InChI=1S/C11H14O6/c1-14-8-4-7(17-6-10(12)13)5-9(15-2)11(8)16-3/h4-5H,6H2,1-3H3,(H,12,13) | DUUIKSNOGTVREZ-UHFFFAOYSA-N | 1.18 | 1 | C11H14O6 | 242.23 | 5 | 1 | 17 | 242.23 | -0.07 | 0 | 74.22 | 0.81 | N | 6 | CHEMBL176835 | CHEMBL176835 | CHEMBL176835 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (5 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,172 | CHEMBL633104 | Solubility ratio ([HbS+drug (10 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | COc1cc(OCC(=O)O)cc(OC)c1OC | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL176835 | null | null | 0 | null | 347,503 | = | 1 | 0 | = | Solubility ratio | null | 1.013 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.013 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | COc1cc(OCC(=O)O)cc(OC)c1OC |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
2.0917 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -2.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -3.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.0792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -1.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -3.8042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -4.6167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6750 -1.3167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.6417 -3.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6542 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -5.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 1 1 0
4 3 2 0
5 2 1 0
6 4 1 0
7 10 1 0
8 7 2 0
9 6 1 0
10 9 1 0
11 1 1 0
12 2 1 0
13 3 1 0
14 7 1 0
15 11 1 0
16 12 1 0
17 13 1 0
6 5 2 0
M END
> <chembl_id>
CHEMBL176835
> <chembl_pref_name>
None | InChI=1S/C11H14O6/c1-14-8-4-7(17-6-10(12)13)5-9(15-2)11(8)16-3/h4-5H,6H2,1-3H3,(H,12,13) | DUUIKSNOGTVREZ-UHFFFAOYSA-N | 1.18 | 1 | C11H14O6 | 242.23 | 5 | 1 | 17 | 242.23 | -0.07 | 0 | 74.22 | 0.81 | N | 6 | CHEMBL176835 | CHEMBL176835 | CHEMBL176835 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (10 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,173 | CHEMBL633105 | Solubility ratio ([HbS+drug (20 mM)]/[HbS-drug] | A | BAO_0000019 | assay format | COc1cc(OCC(=O)O)cc(OC)c1OC | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL176835 | null | null | 0 | null | 347,503 | = | 1 | 0 | = | Solubility ratio | null | 1.015 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.015 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | COc1cc(OCC(=O)O)cc(OC)c1OC |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
2.0917 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -2.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -3.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.0792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -1.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -3.8042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -4.6167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6750 -1.3167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.6417 -3.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6542 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -5.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 1 1 0
4 3 2 0
5 2 1 0
6 4 1 0
7 10 1 0
8 7 2 0
9 6 1 0
10 9 1 0
11 1 1 0
12 2 1 0
13 3 1 0
14 7 1 0
15 11 1 0
16 12 1 0
17 13 1 0
6 5 2 0
M END
> <chembl_id>
CHEMBL176835
> <chembl_pref_name>
None | InChI=1S/C11H14O6/c1-14-8-4-7(17-6-10(12)13)5-9(15-2)11(8)16-3/h4-5H,6H2,1-3H3,(H,12,13) | DUUIKSNOGTVREZ-UHFFFAOYSA-N | 1.18 | 1 | C11H14O6 | 242.23 | 5 | 1 | 17 | 242.23 | -0.07 | 0 | 74.22 | 0.81 | N | 6 | CHEMBL176835 | CHEMBL176835 | CHEMBL176835 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (20 mM)]/[HbS-drug] | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,174 | CHEMBL634599 | Solubility ratio ([HbS+drug (40 mM)]/[HbS-drug]) | A | BAO_0000019 | assay format | COc1cc(OCC(=O)O)cc(OC)c1OC | null | CHEMBL1122711 | J Med Chem | 1,984 | CHEMBL176835 | null | null | 0 | null | 347,503 | = | 1 | 0 | = | Solubility ratio | null | 1.047 | CHEMBL612558 | null | ADMET | null | null | Solubility ratio | null | null | 1.047 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | COc1cc(OCC(=O)O)cc(OC)c1OC |
RDKit 2D
17 17 0 0 0 0 0 0 0 0999 V2000
2.0917 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -2.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -3.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -3.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -2.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -0.0792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2417 -1.3167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -3.8042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.3667 -2.1417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8042 -4.6167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
5.6750 -1.3167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.6417 -3.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6542 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5167 -5.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 1 1 0
4 3 2 0
5 2 1 0
6 4 1 0
7 10 1 0
8 7 2 0
9 6 1 0
10 9 1 0
11 1 1 0
12 2 1 0
13 3 1 0
14 7 1 0
15 11 1 0
16 12 1 0
17 13 1 0
6 5 2 0
M END
> <chembl_id>
CHEMBL176835
> <chembl_pref_name>
None | InChI=1S/C11H14O6/c1-14-8-4-7(17-6-10(12)13)5-9(15-2)11(8)16-3/h4-5H,6H2,1-3H3,(H,12,13) | DUUIKSNOGTVREZ-UHFFFAOYSA-N | 1.18 | 1 | C11H14O6 | 242.23 | 5 | 1 | 17 | 242.23 | -0.07 | 0 | 74.22 | 0.81 | N | 6 | CHEMBL176835 | CHEMBL176835 | CHEMBL176835 | null | null | null | null | Homo sapiens | null | null | 9,606 | null | A | ADME | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Solubility ratio ([HbS+drug (40 mM)]/[HbS-drug]) | CHEMBL1122711 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612558 | null | null | null | null | ADMET | false | ADMET | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | In this paper we further establish the activity of two classes of small molecules, benzyloxy and phenoxy acids, as potent inhibitors of hemoglobin S (HbS) gelation. Structural modifications with a large number of each class confirm our earlier work that the highest activity is observed with compounds that contain dihalogenated aromatic rings with attached polar side chains. We have also found a halogenated aromatic malonic acid derivative to be quite active. Compounds reported in this paper are compared with other antigelling agents studied in our laboratory. Comments are made concerning the antigelling activity and binding sites of four derivatives and their effect on the allosteric mechanism of hemoglobin (Hb) function. | Abraham DJ, Kennedy PE, Mehanna AS, Patwa DC, Williams FL. | 10.1021/jm00374a006 | null | 967 | 8 | J Med Chem | null | 6,747,995 | 1 | Design, synthesis, and testing of potential antisickling agents. 4. Structure-activity relationships of benzyloxy and phenoxy acids. | 27 | 1,984 |
null | 33,177 | CHEMBL688000 | Lowest concentration necessary to induce DNA gyrase-mediated cleavage of DNA | B | BAO_0000223 | protein complex format | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 | null | CHEMBL1124223 | J Med Chem | 1,988 | CHEMBL6299 | null | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 227 | = | 1 | 0 | = | Concentration | ug ml-1 | 10 | CHEMBL2094139 | Escherichia coli | DNA gyrase | 562 | null | Concentration | ug ml-1 | UO_0000274 | 10.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 |
RDKit 2D
30 33 0 0 0 0 0 0 0 0999 V2000
4.7042 -3.9167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4125 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -2.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4167 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -3.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -3.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -3.9250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.7042 -4.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -2.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.1250 -2.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0292 -5.2292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.3667 -5.2250 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
1.0917 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7542 -4.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -1.4417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2917 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1167 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2750 -4.7500 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.1167 -1.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.5417 -4.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -2.2750 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.8417 -2.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.9500 -4.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7708 -4.7792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.2833 -4.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5875 -4.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0708 -5.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 5 2 0
3 1 1 0
4 3 1 0
5 1 1 0
6 3 2 0
7 2 1 0
8 6 1 0
9 8 1 0
10 1 1 0
11 8 2 0
12 4 2 0
13 2 1 0
14 10 2 0
15 10 1 0
16 9 1 0
17 9 1 0
18 7 2 0
19 14 1 0
20 15 1 0
21 6 1 0
22 13 2 0
23 16 1 0
24 11 1 0
25 13 1 0
26 17 1 0
27 28 1 0
28 23 1 0
29 27 1 0
30 29 1 0
19 20 2 0
4 7 1 0
12 11 1 0
23 26 1 0
M END
> <chembl_id>
CHEMBL6299
> <chembl_pref_name>
None | InChI=1S/C20H20F2N4O3S/c1-2-23-8-11-3-5-25(9-11)17-14(21)7-12-16(15(17)22)26(20-24-4-6-30-20)10-13(18(12)27)19(28)29/h4,6-7,10-11,23H,2-3,5,8-9H2,1H3,(H,28,29) | MAVIDMIMQVTJOW-UHFFFAOYSA-N | 2.86 | 3 | C20H20F2N4O3S | 434.47 | 7 | 2 | 30 | 434.47 | -1.16 | 0 | 87.46 | 0.62 | N | 6 | CHEMBL6299 | CHEMBL6299 | CHEMBL6299 | null | null | null | null | Escherichia coli | null | null | 562 | null | B | Binding | BAO_0000223 | protein complex format | null | Direct protein complex subunits assigned | 7 | Lowest concentration necessary to induce DNA gyrase-mediated cleavage of DNA | CHEMBL1124223 | Direct protein target assigned | D | null | 1 | CHEMBL2094139 | null | null | null | Escherichia coli | DNA gyrase | false | PROTEIN COMPLEX | 562 | P0AES6 | DNA gyrase subunit B | PROTEIN | 123 | 2 | null | null | null | null | null | null | null | null | null | null | null | A series of 18 1-substituted 7-[3-[(ethylamino)methyl]-1- pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline- carboxylic acids (N1 analogues of CI-934) were synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Correlations between the inhibition of DNA gyrase and antibacterial potency were established. A quantitative structure-activity relationship (QSAR) was derived by using the antibacterial potency for each of 11 strains of bacteria and the Gram-negative mean. The equations indicated that antibacterial potency was strongly dependent on STERIMOL length and width and the level of unsaturation of the N1 substituent. Some strains also showed a dependence on the presence of heteroatoms (O, N, S) in the N1 group. No significant correlations between gyrase inhibition and combinations of these parameters were found. These QSAR results are discussed in conjunction with the conformational analyses from molecular modeling studies. The substituent that most enhanced the activity of the quinolone in all regards was the cyclopropyl group. This analogue, 1-cyclopropyl-7-[3-[(ethylamino)-methyl]-1-pyrrolidinyl]-6, 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (PD 117558), demonstrated outstanding broad spectrum activity both in vitro and in vivo when compared to relevant standards. | Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF. | 10.1021/jm00400a017 | null | 991 | 5 | J Med Chem | null | 2,834,557 | 1 | 1-Substituted 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8- difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N1 for the quinolone antibacterials. | 31 | 1,988 |
null | 33,178 | CHEMBL689081 | Concentration required for 50% inhibition of gyrase. | B | BAO_0000223 | protein complex format | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 | null | CHEMBL1124223 | J Med Chem | 1,988 | CHEMBL6299 | null | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 227 | = | 1 | 0 | = | Concentration | ug ml-1 | 30 | CHEMBL2094139 | Escherichia coli | DNA gyrase | 562 | null | Concentration | ug ml-1 | UO_0000274 | 30.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 |
RDKit 2D
30 33 0 0 0 0 0 0 0 0999 V2000
4.7042 -3.9167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4125 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -2.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4167 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -3.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -3.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -3.9250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.7042 -4.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -2.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.1250 -2.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0292 -5.2292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.3667 -5.2250 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
1.0917 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7542 -4.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -1.4417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2917 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1167 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2750 -4.7500 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.1167 -1.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.5417 -4.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -2.2750 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.8417 -2.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.9500 -4.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7708 -4.7792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.2833 -4.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5875 -4.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0708 -5.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 5 2 0
3 1 1 0
4 3 1 0
5 1 1 0
6 3 2 0
7 2 1 0
8 6 1 0
9 8 1 0
10 1 1 0
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12 4 2 0
13 2 1 0
14 10 2 0
15 10 1 0
16 9 1 0
17 9 1 0
18 7 2 0
19 14 1 0
20 15 1 0
21 6 1 0
22 13 2 0
23 16 1 0
24 11 1 0
25 13 1 0
26 17 1 0
27 28 1 0
28 23 1 0
29 27 1 0
30 29 1 0
19 20 2 0
4 7 1 0
12 11 1 0
23 26 1 0
M END
> <chembl_id>
CHEMBL6299
> <chembl_pref_name>
None | InChI=1S/C20H20F2N4O3S/c1-2-23-8-11-3-5-25(9-11)17-14(21)7-12-16(15(17)22)26(20-24-4-6-30-20)10-13(18(12)27)19(28)29/h4,6-7,10-11,23H,2-3,5,8-9H2,1H3,(H,28,29) | MAVIDMIMQVTJOW-UHFFFAOYSA-N | 2.86 | 3 | C20H20F2N4O3S | 434.47 | 7 | 2 | 30 | 434.47 | -1.16 | 0 | 87.46 | 0.62 | N | 6 | CHEMBL6299 | CHEMBL6299 | CHEMBL6299 | null | null | null | null | Escherichia coli | null | null | 562 | null | B | Binding | BAO_0000223 | protein complex format | null | Direct protein complex subunits assigned | 7 | Concentration required for 50% inhibition of gyrase. | CHEMBL1124223 | Direct protein target assigned | D | null | 1 | CHEMBL2094139 | null | null | null | Escherichia coli | DNA gyrase | false | PROTEIN COMPLEX | 562 | P0AES6 | DNA gyrase subunit B | PROTEIN | 123 | 2 | null | null | null | null | null | null | null | null | null | null | null | A series of 18 1-substituted 7-[3-[(ethylamino)methyl]-1- pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline- carboxylic acids (N1 analogues of CI-934) were synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Correlations between the inhibition of DNA gyrase and antibacterial potency were established. A quantitative structure-activity relationship (QSAR) was derived by using the antibacterial potency for each of 11 strains of bacteria and the Gram-negative mean. The equations indicated that antibacterial potency was strongly dependent on STERIMOL length and width and the level of unsaturation of the N1 substituent. Some strains also showed a dependence on the presence of heteroatoms (O, N, S) in the N1 group. No significant correlations between gyrase inhibition and combinations of these parameters were found. These QSAR results are discussed in conjunction with the conformational analyses from molecular modeling studies. The substituent that most enhanced the activity of the quinolone in all regards was the cyclopropyl group. This analogue, 1-cyclopropyl-7-[3-[(ethylamino)-methyl]-1-pyrrolidinyl]-6, 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (PD 117558), demonstrated outstanding broad spectrum activity both in vitro and in vivo when compared to relevant standards. | Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF. | 10.1021/jm00400a017 | null | 991 | 5 | J Med Chem | null | 2,834,557 | 1 | 1-Substituted 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8- difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N1 for the quinolone antibacterials. | 31 | 1,988 |
null | 33,179 | CHEMBL677348 | Minimum inhibitory concentration against Escherichia coli (H560) | F | BAO_0000218 | organism-based format | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 | null | CHEMBL1124223 | J Med Chem | 1,988 | CHEMBL6299 | null | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 227 | = | 1 | 1 | = | MIC | ug.mL-1 | 3.1 | CHEMBL354 | Escherichia coli | Escherichia coli | 562 | null | MIC | ug ml-1 | UO_0000274 | 3.1 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 |
RDKit 2D
30 33 0 0 0 0 0 0 0 0999 V2000
4.7042 -3.9167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4125 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -2.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4167 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -3.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -3.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -3.9250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.7042 -4.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -2.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.1250 -2.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0292 -5.2292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.3667 -5.2250 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
1.0917 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7542 -4.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -1.4417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2917 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1167 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2750 -4.7500 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.1167 -1.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.5417 -4.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -2.2750 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.8417 -2.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.9500 -4.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7708 -4.7792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.2833 -4.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5875 -4.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0708 -5.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 5 2 0
3 1 1 0
4 3 1 0
5 1 1 0
6 3 2 0
7 2 1 0
8 6 1 0
9 8 1 0
10 1 1 0
11 8 2 0
12 4 2 0
13 2 1 0
14 10 2 0
15 10 1 0
16 9 1 0
17 9 1 0
18 7 2 0
19 14 1 0
20 15 1 0
21 6 1 0
22 13 2 0
23 16 1 0
24 11 1 0
25 13 1 0
26 17 1 0
27 28 1 0
28 23 1 0
29 27 1 0
30 29 1 0
19 20 2 0
4 7 1 0
12 11 1 0
23 26 1 0
M END
> <chembl_id>
CHEMBL6299
> <chembl_pref_name>
None | InChI=1S/C20H20F2N4O3S/c1-2-23-8-11-3-5-25(9-11)17-14(21)7-12-16(15(17)22)26(20-24-4-6-30-20)10-13(18(12)27)19(28)29/h4,6-7,10-11,23H,2-3,5,8-9H2,1H3,(H,28,29) | MAVIDMIMQVTJOW-UHFFFAOYSA-N | 2.86 | 3 | C20H20F2N4O3S | 434.47 | 7 | 2 | 30 | 434.47 | -1.16 | 0 | 87.46 | 0.62 | N | 6 | CHEMBL6299 | CHEMBL6299 | CHEMBL6299 | null | null | null | null | Escherichia coli | null | null | 562 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Minimum inhibitory concentration against Escherichia coli (H560) | CHEMBL1124223 | Non-molecular target assigned | N | null | 1 | CHEMBL354 | null | null | null | Escherichia coli | Escherichia coli | false | ORGANISM | 562 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of 18 1-substituted 7-[3-[(ethylamino)methyl]-1- pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline- carboxylic acids (N1 analogues of CI-934) were synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Correlations between the inhibition of DNA gyrase and antibacterial potency were established. A quantitative structure-activity relationship (QSAR) was derived by using the antibacterial potency for each of 11 strains of bacteria and the Gram-negative mean. The equations indicated that antibacterial potency was strongly dependent on STERIMOL length and width and the level of unsaturation of the N1 substituent. Some strains also showed a dependence on the presence of heteroatoms (O, N, S) in the N1 group. No significant correlations between gyrase inhibition and combinations of these parameters were found. These QSAR results are discussed in conjunction with the conformational analyses from molecular modeling studies. The substituent that most enhanced the activity of the quinolone in all regards was the cyclopropyl group. This analogue, 1-cyclopropyl-7-[3-[(ethylamino)-methyl]-1-pyrrolidinyl]-6, 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (PD 117558), demonstrated outstanding broad spectrum activity both in vitro and in vivo when compared to relevant standards. | Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF. | 10.1021/jm00400a017 | null | 991 | 5 | J Med Chem | null | 2,834,557 | 1 | 1-Substituted 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8- difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N1 for the quinolone antibacterials. | 31 | 1,988 |
null | 33,180 | CHEMBL677349 | Minimum inhibitory concentration against Escherichia coli (vogel) | F | BAO_0000218 | organism-based format | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 | null | CHEMBL1124223 | J Med Chem | 1,988 | CHEMBL6299 | null | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 227 | = | 1 | 1 | = | MIC | ug.mL-1 | 1.6 | CHEMBL354 | Escherichia coli | Escherichia coli | 562 | null | MIC | ug ml-1 | UO_0000274 | 1.6 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 |
RDKit 2D
30 33 0 0 0 0 0 0 0 0999 V2000
4.7042 -3.9167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4125 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -2.6792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4167 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -3.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -3.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -3.9250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.7042 -4.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5542 -2.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2667 -2.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.1250 -2.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0292 -5.2292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.3667 -5.2250 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
1.0917 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7542 -4.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.6917 -1.4417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.2917 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.1167 -6.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2750 -4.7500 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.1167 -1.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.5417 -4.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.8417 -2.2750 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
6.8417 -2.6667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
0.9500 -4.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7708 -4.7792 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.2833 -4.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5875 -4.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.0708 -5.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 5 2 0
3 1 1 0
4 3 1 0
5 1 1 0
6 3 2 0
7 2 1 0
8 6 1 0
9 8 1 0
10 1 1 0
11 8 2 0
12 4 2 0
13 2 1 0
14 10 2 0
15 10 1 0
16 9 1 0
17 9 1 0
18 7 2 0
19 14 1 0
20 15 1 0
21 6 1 0
22 13 2 0
23 16 1 0
24 11 1 0
25 13 1 0
26 17 1 0
27 28 1 0
28 23 1 0
29 27 1 0
30 29 1 0
19 20 2 0
4 7 1 0
12 11 1 0
23 26 1 0
M END
> <chembl_id>
CHEMBL6299
> <chembl_pref_name>
None | InChI=1S/C20H20F2N4O3S/c1-2-23-8-11-3-5-25(9-11)17-14(21)7-12-16(15(17)22)26(20-24-4-6-30-20)10-13(18(12)27)19(28)29/h4,6-7,10-11,23H,2-3,5,8-9H2,1H3,(H,28,29) | MAVIDMIMQVTJOW-UHFFFAOYSA-N | 2.86 | 3 | C20H20F2N4O3S | 434.47 | 7 | 2 | 30 | 434.47 | -1.16 | 0 | 87.46 | 0.62 | N | 6 | CHEMBL6299 | CHEMBL6299 | CHEMBL6299 | null | null | null | null | Escherichia coli | null | null | 562 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Minimum inhibitory concentration against Escherichia coli (vogel) | CHEMBL1124223 | Non-molecular target assigned | N | null | 1 | CHEMBL354 | null | null | null | Escherichia coli | Escherichia coli | false | ORGANISM | 562 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of 18 1-substituted 7-[3-[(ethylamino)methyl]-1- pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline- carboxylic acids (N1 analogues of CI-934) were synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Correlations between the inhibition of DNA gyrase and antibacterial potency were established. A quantitative structure-activity relationship (QSAR) was derived by using the antibacterial potency for each of 11 strains of bacteria and the Gram-negative mean. The equations indicated that antibacterial potency was strongly dependent on STERIMOL length and width and the level of unsaturation of the N1 substituent. Some strains also showed a dependence on the presence of heteroatoms (O, N, S) in the N1 group. No significant correlations between gyrase inhibition and combinations of these parameters were found. These QSAR results are discussed in conjunction with the conformational analyses from molecular modeling studies. The substituent that most enhanced the activity of the quinolone in all regards was the cyclopropyl group. This analogue, 1-cyclopropyl-7-[3-[(ethylamino)-methyl]-1-pyrrolidinyl]-6, 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (PD 117558), demonstrated outstanding broad spectrum activity both in vitro and in vivo when compared to relevant standards. | Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF. | 10.1021/jm00400a017 | null | 991 | 5 | J Med Chem | null | 2,834,557 | 1 | 1-Substituted 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8- difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N1 for the quinolone antibacterials. | 31 | 1,988 |
null | 33,181 | CHEMBL700973 | Minimum inhibitory concentration against Klebsiella pneumoniae (MGH-2) | F | BAO_0000218 | organism-based format | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 | null | CHEMBL1124223 | J Med Chem | 1,988 | CHEMBL6299 | null | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 227 | = | 1 | 1 | = | MIC | ug.mL-1 | 3.1 | CHEMBL350 | Klebsiella pneumoniae | Klebsiella pneumoniae | 573 | null | MIC | ug ml-1 | UO_0000274 | 3.1 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 |
RDKit 2D
30 33 0 0 0 0 0 0 0 0999 V2000
4.7042 -3.9167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4125 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9875 -3.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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M END
> <chembl_id>
CHEMBL6299
> <chembl_pref_name>
None | InChI=1S/C20H20F2N4O3S/c1-2-23-8-11-3-5-25(9-11)17-14(21)7-12-16(15(17)22)26(20-24-4-6-30-20)10-13(18(12)27)19(28)29/h4,6-7,10-11,23H,2-3,5,8-9H2,1H3,(H,28,29) | MAVIDMIMQVTJOW-UHFFFAOYSA-N | 2.86 | 3 | C20H20F2N4O3S | 434.47 | 7 | 2 | 30 | 434.47 | -1.16 | 0 | 87.46 | 0.62 | N | 6 | CHEMBL6299 | CHEMBL6299 | CHEMBL6299 | null | null | null | null | Klebsiella pneumoniae | null | null | 573 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Minimum inhibitory concentration against Klebsiella pneumoniae (MGH-2) | CHEMBL1124223 | Non-molecular target assigned | N | null | 1 | CHEMBL350 | null | null | null | Klebsiella pneumoniae | Klebsiella pneumoniae | false | ORGANISM | 573 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of 18 1-substituted 7-[3-[(ethylamino)methyl]-1- pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline- carboxylic acids (N1 analogues of CI-934) were synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Correlations between the inhibition of DNA gyrase and antibacterial potency were established. A quantitative structure-activity relationship (QSAR) was derived by using the antibacterial potency for each of 11 strains of bacteria and the Gram-negative mean. The equations indicated that antibacterial potency was strongly dependent on STERIMOL length and width and the level of unsaturation of the N1 substituent. Some strains also showed a dependence on the presence of heteroatoms (O, N, S) in the N1 group. No significant correlations between gyrase inhibition and combinations of these parameters were found. These QSAR results are discussed in conjunction with the conformational analyses from molecular modeling studies. The substituent that most enhanced the activity of the quinolone in all regards was the cyclopropyl group. This analogue, 1-cyclopropyl-7-[3-[(ethylamino)-methyl]-1-pyrrolidinyl]-6, 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (PD 117558), demonstrated outstanding broad spectrum activity both in vitro and in vivo when compared to relevant standards. | Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF. | 10.1021/jm00400a017 | null | 991 | 5 | J Med Chem | null | 2,834,557 | 1 | 1-Substituted 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8- difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N1 for the quinolone antibacterials. | 31 | 1,988 |
null | 33,182 | CHEMBL772086 | Minimum inhibitory concentration against Providencia rettgeri. (M1771) | F | BAO_0000218 | organism-based format | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 | null | CHEMBL1124223 | J Med Chem | 1,988 | CHEMBL6299 | null | null | 0 | http://www.openphacts.org/units/MicrogramPerMilliliter | 227 | = | 1 | 1 | = | MIC | ug.mL-1 | 12.5 | CHEMBL612537 | Providencia rettgeri | Providencia rettgeri | 587 | null | MIC | ug ml-1 | UO_0000274 | 12.5 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCNCC1CCN(c2c(F)cc3c(=O)c(C(=O)O)cn(-c4nccs4)c3c2F)C1 |
RDKit 2D
30 33 0 0 0 0 0 0 0 0999 V2000
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M END
> <chembl_id>
CHEMBL6299
> <chembl_pref_name>
None | InChI=1S/C20H20F2N4O3S/c1-2-23-8-11-3-5-25(9-11)17-14(21)7-12-16(15(17)22)26(20-24-4-6-30-20)10-13(18(12)27)19(28)29/h4,6-7,10-11,23H,2-3,5,8-9H2,1H3,(H,28,29) | MAVIDMIMQVTJOW-UHFFFAOYSA-N | 2.86 | 3 | C20H20F2N4O3S | 434.47 | 7 | 2 | 30 | 434.47 | -1.16 | 0 | 87.46 | 0.62 | N | 6 | CHEMBL6299 | CHEMBL6299 | CHEMBL6299 | null | null | null | null | Providencia rettgeri | null | null | 587 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Minimum inhibitory concentration against Providencia rettgeri. (M1771) | CHEMBL1124223 | Non-molecular target assigned | N | null | 1 | CHEMBL612537 | null | null | null | Providencia rettgeri | Providencia rettgeri | false | ORGANISM | 587 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of 18 1-substituted 7-[3-[(ethylamino)methyl]-1- pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline- carboxylic acids (N1 analogues of CI-934) were synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition. Correlations between the inhibition of DNA gyrase and antibacterial potency were established. A quantitative structure-activity relationship (QSAR) was derived by using the antibacterial potency for each of 11 strains of bacteria and the Gram-negative mean. The equations indicated that antibacterial potency was strongly dependent on STERIMOL length and width and the level of unsaturation of the N1 substituent. Some strains also showed a dependence on the presence of heteroatoms (O, N, S) in the N1 group. No significant correlations between gyrase inhibition and combinations of these parameters were found. These QSAR results are discussed in conjunction with the conformational analyses from molecular modeling studies. The substituent that most enhanced the activity of the quinolone in all regards was the cyclopropyl group. This analogue, 1-cyclopropyl-7-[3-[(ethylamino)-methyl]-1-pyrrolidinyl]-6, 8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (PD 117558), demonstrated outstanding broad spectrum activity both in vitro and in vivo when compared to relevant standards. | Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF. | 10.1021/jm00400a017 | null | 991 | 5 | J Med Chem | null | 2,834,557 | 1 | 1-Substituted 7-[3-[(ethylamino)methyl]-1-pyrrolidinyl]-6,8- difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N1 for the quinolone antibacterials. | 31 | 1,988 |
null | 38,115 | CHEMBL796079 | Negative logarithm of the concentration of compound required to reduce the response of EC50 dose of ANG II to the response to half the EC50 dose | F | BAO_0000218 | organism-based format | CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccc(O)cc1)N(C)C(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)C(C)(C)NC)C(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)O | null | CHEMBL1124158 | J Med Chem | 1,988 | CHEMBL262226 | null | 6 | 0 | http://www.openphacts.org/units/Nanomolar | 48,159 | = | 1 | 1 | = | Kd | nM | 1,000 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | pA2 | null | UO_0000065 | 6.0 | null | null | null | null | -1 | 0 | -1 | null | PEPTIDE1{[Me_Aib].R.V.[meY].I.H.P.F}$$$$ | -1 | null | Protein | 0 | false | false | 0 | null | -1 | BOTH | false | false | null | null | false | CC[C@H](C)[C@H](NC(=O)[C@H](Cc1ccc(O)cc1)N(C)C(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)C(C)(C)NC)C(C)C)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)O |
RDKit 2D
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M END
> <chembl_id>
CHEMBL262226
> <chembl_pref_name>
None | InChI=1S/C52H77N13O10/c1-9-31(4)42(46(70)59-37(27-34-28-56-29-58-34)47(71)65-24-14-18-39(65)44(68)60-38(49(73)74)25-32-15-11-10-12-16-32)63-45(69)40(26-33-19-21-35(66)22-20-33)64(8)48(72)41(30(2)3)62-43(67)36(17-13-23-57-51(53)54)61-50(75)52(5,6)55-7/h10-12,15-16,19-22,28-31,36-42,55,66H,9,13-14,17-18,23-27H2,1-8H3,(H,56,58)(H,59,70)(H,60,68)(H,61,75)(H,62,67)(H,63,69)(H,73,74)(H4,53,54,57)/t31-,36-,37-,38-,39-,40-,41-,42-/m0/s1 | OQIKRTPSWNAWRM-DDLCQNJHSA-N | null | null | C52H77N13O10 | 1044.27 | null | null | null | 1,044.27 | null | null | null | null | null | null | CHEMBL262226 | CHEMBL262226 | CHEMBL262226 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Negative logarithm of the concentration of compound required to reduce the response of EC50 dose of ANG II to the response to half the EC50 dose | CHEMBL1124158 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Analogues of the competitive angiotensin antagonist [Sar1,Tyr(ME)4]angiotensin II (sarmesin) with modifications at the N-terminus have been prepared by the solid-phase method and purified by reversed-phase HPLC. Substitution of the Sar1 residue of sarmesin with N,N-dimethyl-Gly, N-ethyl-Gly, aminoisobutyric, (methylamino)isobutyric, aminocaproic, and oxamic acids gave analogues that had the following respective antagonist activities (pA2) in the rat isolated uterus assay: less than 6, 6.9, 5.5, 6.0, less than 6, and 5.3. The additional substitution of Ile for Phe at the C-terminus of the latter four peptides gave pA2 values of 7.1, 5.1, less than 5, and 5. Substitution of the Arg2 residue of sarmesin with Nle or Sar abolished antagonist activity. These data emphasize the stringent and discriminating structural requirements in the N-terminal domain of sarmesin that endow this analogue with its antagonist properties and suggest the presence of defined steric constraints in this region of the molecule during receptor blockade. | Matsoukas J, Cordopatis P, Belte U, Goghari MH, Ganter RC, Franklin KJ, Moore GJ. | 10.1021/jm00402a028 | null | 1418 | 7 | J Med Chem | null | 2,455,051 | 1 | Importance of the N-terminal domain of the type II angiotensin antagonist sarmesin for receptor blockade. | 31 | 1,988 |
null | 38,118 | CHEMBL630713 | Compound (1 mM) was evaluated in vitro for the effect on rate of aging(rate constant) of Soman-inhibited rat erythrocyte AChE and first order rate constant was determined | A | BAO_0000218 | organism-based format | C[N+](C)(C)CCCCl.[Br-] | null | CHEMBL1123058 | J Med Chem | 1,985 | CHEMBL15795 | null | null | 0 | null | 17,688 | = | 1 | 0 | = | Rate constant | null | 0.0359 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Rate constant | null | null | 0.0359 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | C[N+](C)(C)CCCCl.[Br-] |
RDKit 2D
9 7 0 0 0 0 0 0 0 0999 V2000
4.7125 -1.9667 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.1667 -2.5542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.3125 -2.5542 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.7417 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4542 -2.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8792 -2.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.1667 -1.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3792 -3.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0292 -2.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 9 1 0
4 5 1 0
5 2 1 0
6 2 1 0
7 2 1 0
8 2 1 0
9 4 1 0
M CHG 2 1 -1 2 1
M END
> <chembl_id>
CHEMBL15795
> <chembl_pref_name>
None | InChI=1S/C6H15ClN.BrH/c1-8(2,3)6-4-5-7;/h4-6H2,1-3H3;1H/q+1;/p-1 | XMRUUKXYPYSSLI-UHFFFAOYSA-M | 1.32 | 0 | C6H15BrClN | 216.55 | 0 | 0 | 8 | 136.65 | 0.63 | 0 | 0 | 0.41 | Y | 3 | CHEMBL1178211 | CHEMBL15795 | CHEMBL1178211 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | null | A | ADME | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Compound (1 mM) was evaluated in vitro for the effect on rate of aging(rate constant) of Soman-inhibited rat erythrocyte AChE and first order rate constant was determined | CHEMBL1123058 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A number of compounds were synthesized and tested for their ability to realkylate the phosphonate anion of "aged", soman-inhibited acetylcholinesterase. None were found able to do so, but two of the compounds in particular, [2-(4-pyridyl)ethyl]diethylmethylammonium iodide (6) and its 2-isomer 7, proved able to slow the rate of aging significantly. | Gray AP, Platz RD, Chang TC, Leverone TR, Ferrick DA, Kramer DN. | 10.1021/jm00379a020 | null | 111 | 1 | J Med Chem | null | 3,965,704 | 1 | Synthesis of some quaternary ammonium alkylating agents and their effects on soman-inhibited acetylcholinesterase. | 28 | 1,985 |
null | 38,119 | CHEMBL852817 | Ratio of control/treated value of the compound | F | BAO_0000019 | assay format | C[N+](C)(C)CCCCl.[Br-] | null | CHEMBL1123058 | J Med Chem | 1,985 | CHEMBL15795 | null | null | 0 | null | 17,688 | = | 1 | 0 | = | Ratio | null | 1.19 | CHEMBL612545 | null | Unchecked | null | null | Ratio | null | null | 1.19 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | C[N+](C)(C)CCCCl.[Br-] |
RDKit 2D
9 7 0 0 0 0 0 0 0 0999 V2000
4.7125 -1.9667 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.1667 -2.5542 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.3125 -2.5542 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.7417 -2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4542 -2.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.8792 -2.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.1667 -1.7292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.3792 -3.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0292 -2.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 9 1 0
4 5 1 0
5 2 1 0
6 2 1 0
7 2 1 0
8 2 1 0
9 4 1 0
M CHG 2 1 -1 2 1
M END
> <chembl_id>
CHEMBL15795
> <chembl_pref_name>
None | InChI=1S/C6H15ClN.BrH/c1-8(2,3)6-4-5-7;/h4-6H2,1-3H3;1H/q+1;/p-1 | XMRUUKXYPYSSLI-UHFFFAOYSA-M | 1.32 | 0 | C6H15BrClN | 216.55 | 0 | 0 | 8 | 136.65 | 0.63 | 0 | 0 | 0.41 | Y | 3 | CHEMBL1178211 | CHEMBL15795 | CHEMBL1178211 | null | null | null | null | null | null | null | null | null | F | Functional | BAO_0000019 | assay format | null | Default value - Target unknown or has yet to be assigned | 0 | Ratio of control/treated value of the compound | CHEMBL1123058 | Default value - Target has yet to be curated | U | null | 1 | CHEMBL612545 | null | null | null | null | Unchecked | false | UNCHECKED | null | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A number of compounds were synthesized and tested for their ability to realkylate the phosphonate anion of "aged", soman-inhibited acetylcholinesterase. None were found able to do so, but two of the compounds in particular, [2-(4-pyridyl)ethyl]diethylmethylammonium iodide (6) and its 2-isomer 7, proved able to slow the rate of aging significantly. | Gray AP, Platz RD, Chang TC, Leverone TR, Ferrick DA, Kramer DN. | 10.1021/jm00379a020 | null | 111 | 1 | J Med Chem | null | 3,965,704 | 1 | Synthesis of some quaternary ammonium alkylating agents and their effects on soman-inhibited acetylcholinesterase. | 28 | 1,985 |
null | 38,120 | CHEMBL758714 | Inhibition against porcine pancreatic elastase | B | BAO_0000224 | protein format | O=C(Nc1ccccc1)n1ccnc1 | null | CHEMBL1122889 | J Med Chem | 1,985 | CHEMBL294113 | IMIDAZOLE-1-CARBOXYLIC ACID PHENYLAMIDE | null | 0 | null | 113,308 | = | 1 | 0 | = | Activity | null | null | CHEMBL2096984 | Sus scrofa | Pancreatic elastase | 9823 | null | Activity | null | null | null | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | IMIDAZOLE-1-CARBOXYLIC ACID PHENYLAMIDE | -1 | MOL | false | false | null | null | false | O=C(Nc1ccccc1)n1ccnc1 |
RDKit 2D
14 15 0 0 0 0 0 0 0 0999 V2000
8.9167 -8.3292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
8.9250 -7.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.5000 -9.6042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
9.6417 -7.1000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
8.2417 -8.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.5750 -8.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.2125 -7.0875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
9.3167 -9.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.6500 -6.2750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.3667 -5.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.9417 -5.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.9417 -5.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.3792 -5.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.6667 -4.6292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 5 2 0
4 2 1 0
5 1 1 0
6 1 1 0
7 2 2 0
8 6 2 0
9 4 1 0
10 9 2 0
11 9 1 0
12 11 2 0
13 10 1 0
14 12 1 0
3 8 1 0
13 14 2 0
M END
> <chembl_id>
CHEMBL294113
> <chembl_pref_name>
IMIDAZOLE-1-CARBOXYLIC ACID PHENYLAMIDE | InChI=1S/C10H9N3O/c14-10(13-7-6-11-8-13)12-9-4-2-1-3-5-9/h1-8H,(H,12,14) | KPPADAGTNGHGBR-UHFFFAOYSA-N | 1.96 | 2 | C10H9N3O | 187.20 | 3 | 1 | 14 | 187.2 | -1.62 | 0 | 46.92 | 0.74 | Y | 1 | CHEMBL294113 | CHEMBL294113 | CHEMBL294113 | null | null | null | null | null | null | null | null | null | B | Binding | BAO_0000224 | protein format | null | Multiple homologous protein targets may be assigned | 4 | Inhibition against porcine pancreatic elastase | CHEMBL1122889 | Homologous protein target assigned | H | null | 1 | CHEMBL2096984 | null | null | null | Sus scrofa | Pancreatic elastase | false | PROTEIN FAMILY | 9,823 | P08419 | Chymotrypsin-like elastase family member 2A | PROTEIN | 748 | 2 | null | null | null | null | null | null | null | null | null | null | null | Several amino acid derived azolides (I) have been synthesized and investigated for their inhibitory activity toward human leukocyte elastase and porcine pancreatic elastase. The inhibitory activity was found to be dependent on the nature of the precursor amino acid ester. Thus, compounds derived from L-valine methyl ester 3, L-norvaline methyl ester 5, DL-norleucine methyl ester 9, and L-methionine methyl ester 10 were found to inhibit irreversibly both enzymes. Compound 10 was found to be a specific and selective inhibitor of human leukocyte elastase. In contrast to these, inhibitors derived from glycine methyl ester 1, D-valine methyl ester 4, and D-norvaline methyl ester 6 were found to be inactive. The results of the present study show that latent isocyanates derived from appropriate amino acids can serve as selective inhibitors of serine proteases and are of potential pharmacological value. | Groutas WC, Abrams WR, Theodorakis MC, Kasper AM, Rude SA, Badger RC, Ocain TD, Miller KE, Moi MK, Brubaker MJ. | 10.1021/jm00380a010 | null | 204 | 2 | J Med Chem | null | 3,844,034 | 1 | Amino acid derived latent isocyanates: irreversible inactivation of porcine pancreatic elastase and human leukocyte elastase. | 28 | 1,985 |
null | 38,121 | CHEMBL705697 | Inhibition of human leukocyte elastase | B | BAO_0000357 | single protein format | O=C(Nc1ccccc1)n1ccnc1 | null | CHEMBL1122889 | J Med Chem | 1,985 | CHEMBL294113 | IMIDAZOLE-1-CARBOXYLIC ACID PHENYLAMIDE | null | 0 | null | 113,308 | = | 1 | 0 | = | Activity | null | null | CHEMBL248 | Homo sapiens | Neutrophil elastase | 9606 | null | Activity | null | null | null | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | IMIDAZOLE-1-CARBOXYLIC ACID PHENYLAMIDE | -1 | MOL | false | false | null | null | false | O=C(Nc1ccccc1)n1ccnc1 |
RDKit 2D
14 15 0 0 0 0 0 0 0 0999 V2000
8.9167 -8.3292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
8.9250 -7.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.5000 -9.6042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
9.6417 -7.1000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
8.2417 -8.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.5750 -8.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.2125 -7.0875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
9.3167 -9.6042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.6500 -6.2750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.3667 -5.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.9417 -5.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.9417 -5.0417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.3792 -5.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.6667 -4.6292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 1 0
3 5 2 0
4 2 1 0
5 1 1 0
6 1 1 0
7 2 2 0
8 6 2 0
9 4 1 0
10 9 2 0
11 9 1 0
12 11 2 0
13 10 1 0
14 12 1 0
3 8 1 0
13 14 2 0
M END
> <chembl_id>
CHEMBL294113
> <chembl_pref_name>
IMIDAZOLE-1-CARBOXYLIC ACID PHENYLAMIDE | InChI=1S/C10H9N3O/c14-10(13-7-6-11-8-13)12-9-4-2-1-3-5-9/h1-8H,(H,12,14) | KPPADAGTNGHGBR-UHFFFAOYSA-N | 1.96 | 2 | C10H9N3O | 187.20 | 3 | 1 | 14 | 187.2 | -1.62 | 0 | 46.92 | 0.74 | Y | 1 | CHEMBL294113 | CHEMBL294113 | CHEMBL294113 | null | null | null | null | null | null | null | null | null | B | Binding | BAO_0000357 | single protein format | null | Homologous single protein target assigned | 8 | Inhibition of human leukocyte elastase | CHEMBL1122889 | Homologous protein target assigned | H | null | 1 | CHEMBL248 | null | null | null | Homo sapiens | Neutrophil elastase | false | SINGLE PROTEIN | 9,606 | P08246 | Neutrophil elastase | PROTEIN | 366 | 1 | null | null | null | null | null | null | null | null | null | null | null | Several amino acid derived azolides (I) have been synthesized and investigated for their inhibitory activity toward human leukocyte elastase and porcine pancreatic elastase. The inhibitory activity was found to be dependent on the nature of the precursor amino acid ester. Thus, compounds derived from L-valine methyl ester 3, L-norvaline methyl ester 5, DL-norleucine methyl ester 9, and L-methionine methyl ester 10 were found to inhibit irreversibly both enzymes. Compound 10 was found to be a specific and selective inhibitor of human leukocyte elastase. In contrast to these, inhibitors derived from glycine methyl ester 1, D-valine methyl ester 4, and D-norvaline methyl ester 6 were found to be inactive. The results of the present study show that latent isocyanates derived from appropriate amino acids can serve as selective inhibitors of serine proteases and are of potential pharmacological value. | Groutas WC, Abrams WR, Theodorakis MC, Kasper AM, Rude SA, Badger RC, Ocain TD, Miller KE, Moi MK, Brubaker MJ. | 10.1021/jm00380a010 | null | 204 | 2 | J Med Chem | null | 3,844,034 | 1 | Amino acid derived latent isocyanates: irreversible inactivation of porcine pancreatic elastase and human leukocyte elastase. | 28 | 1,985 |
null | 38,122 | CHEMBL785434 | Effective dose against DOPA accumulation in rat brain limbic region after reserpine pretreatment by subcutaneous administration | F | BAO_0000218 | organism-based format | CCCN(CCC)[C@H]1CCc2c(OC)cccc2[C@H]1C.Cl | null | CHEMBL1122913 | J Med Chem | 1,985 | CHEMBL544195 | null | null | 0 | null | 5,909 | = | 1 | 1 | = | ED50 | mg.kg-1 | 1.7 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | ED50 | mg kg-1 | UO_0000308 | 1.7 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCN(CCC)[C@H]1CCc2c(OC)cccc2[C@H]1C.Cl |
RDKit 2D
21 21 0 0 0 0 0 0 0 0999 V2000
3.8893 2.1804 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 2.8580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2873 2.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2873 1.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 1.2080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 1.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 2.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 2.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.1417 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.1417 1.6206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 1.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8561 2.8581 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8561 3.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 4.0956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 4.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.2851 2.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.9996 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 0.3830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 -0.0295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 3.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 1 0
2 7 2 0
4 5 1 0
5 6 2 0
6 7 1 0
3 8 1 0
3 4 2 0
11 4 1 0
8 9 1 0
9 10 1 0
10 11 1 0
9 12 1 6
12 13 1 0
12 14 1 0
14 15 1 0
15 16 1 0
13 17 1 0
17 18 1 0
5 19 1 0
19 20 1 0
8 21 1 6
M END
> <chembl_id>
CHEMBL544195
> <chembl_pref_name>
None | InChI=1S/C18H29NO.ClH/c1-5-12-19(13-6-2)17-11-10-16-15(14(17)3)8-7-9-18(16)20-4;/h7-9,14,17H,5-6,10-13H2,1-4H3;1H/t14-,17+;/m1./s1 | ADVQBNGWEGSMGY-CVLQQERVSA-N | 4.24 | 1 | C18H30ClNO | 311.90 | 2 | 0 | 20 | 275.44 | 0.02 | 0 | 12.47 | 0.77 | N | 6 | CHEMBL157937 | CHEMBL544195 | CHEMBL157937 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Brain | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Effective dose against DOPA accumulation in rat brain limbic region after reserpine pretreatment by subcutaneous administration | CHEMBL1122913 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638188 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The enantiomers of cis-5-hydroxy-1-methyl-2-(di-n-propylamino)tetralin and its methyl ether have been synthesized. The compounds were tested for central dopamine (DA) receptor activity, by using biochemical and behavioral tests in rats. The (1R,2S)-(-) enantiomers of 1 and 2 are characterized as centrally acting DA-receptor agonists while the corresponding (1S,2R)-(+) enantiomers are characterized as centrally acting DA-receptor antagonists. Compounds (+)-1 and (+)-2 differ from classical neuroleptics in being able to increase DA synthesis rate in a wide dose range without reducing locomotor activity, suggesting a pronounced selectivity for DA autoreceptors. Also the (-) enantiomers seem to act preferentially on DA autoreceptors. | Johansson AM, Arvidsson LE, Hacksell U, Nilsson JL, Svensson K, Hjorth S, Clark D, Carlsson A, Sanchez D, Andersson B. | 10.1021/jm00146a012 | null | 1049 | 8 | J Med Chem | null | 3,927,002 | 1 | Novel dopamine receptor agonists and antagonists with preferential action on autoreceptors. | 28 | 1,985 |
null | 38,123 | CHEMBL785439 | Effective dose against DOPA accumulation in rat brain striatal region after reserpine pretreatment by subcutaneous administration | F | BAO_0000218 | organism-based format | CCCN(CCC)[C@H]1CCc2c(OC)cccc2[C@H]1C.Cl | null | CHEMBL1122913 | J Med Chem | 1,985 | CHEMBL544195 | null | null | 0 | null | 5,909 | = | 1 | 1 | = | ED50 | mg.kg-1 | 1.8 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | ED50 | mg kg-1 | UO_0000308 | 1.8 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCN(CCC)[C@H]1CCc2c(OC)cccc2[C@H]1C.Cl |
RDKit 2D
21 21 0 0 0 0 0 0 0 0999 V2000
3.8893 2.1804 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 2.8580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2873 2.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2873 1.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 1.2080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 1.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 2.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 2.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.1417 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.1417 1.6206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 1.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8561 2.8581 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8561 3.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 4.0956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 4.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.2851 2.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.9996 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 0.3830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 -0.0295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 3.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 1 0
2 7 2 0
4 5 1 0
5 6 2 0
6 7 1 0
3 8 1 0
3 4 2 0
11 4 1 0
8 9 1 0
9 10 1 0
10 11 1 0
9 12 1 6
12 13 1 0
12 14 1 0
14 15 1 0
15 16 1 0
13 17 1 0
17 18 1 0
5 19 1 0
19 20 1 0
8 21 1 6
M END
> <chembl_id>
CHEMBL544195
> <chembl_pref_name>
None | InChI=1S/C18H29NO.ClH/c1-5-12-19(13-6-2)17-11-10-16-15(14(17)3)8-7-9-18(16)20-4;/h7-9,14,17H,5-6,10-13H2,1-4H3;1H/t14-,17+;/m1./s1 | ADVQBNGWEGSMGY-CVLQQERVSA-N | 4.24 | 1 | C18H30ClNO | 311.90 | 2 | 0 | 20 | 275.44 | 0.02 | 0 | 12.47 | 0.77 | N | 6 | CHEMBL157937 | CHEMBL544195 | CHEMBL157937 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | Brain | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Effective dose against DOPA accumulation in rat brain striatal region after reserpine pretreatment by subcutaneous administration | CHEMBL1122913 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | CHEMBL3638188 | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The enantiomers of cis-5-hydroxy-1-methyl-2-(di-n-propylamino)tetralin and its methyl ether have been synthesized. The compounds were tested for central dopamine (DA) receptor activity, by using biochemical and behavioral tests in rats. The (1R,2S)-(-) enantiomers of 1 and 2 are characterized as centrally acting DA-receptor agonists while the corresponding (1S,2R)-(+) enantiomers are characterized as centrally acting DA-receptor antagonists. Compounds (+)-1 and (+)-2 differ from classical neuroleptics in being able to increase DA synthesis rate in a wide dose range without reducing locomotor activity, suggesting a pronounced selectivity for DA autoreceptors. Also the (-) enantiomers seem to act preferentially on DA autoreceptors. | Johansson AM, Arvidsson LE, Hacksell U, Nilsson JL, Svensson K, Hjorth S, Clark D, Carlsson A, Sanchez D, Andersson B. | 10.1021/jm00146a012 | null | 1049 | 8 | J Med Chem | null | 3,927,002 | 1 | Novel dopamine receptor agonists and antagonists with preferential action on autoreceptors. | 28 | 1,985 |
null | 38,126 | CHEMBL773735 | Locomotor activity after reserpine pretreatment in rat | F | BAO_0000218 | organism-based format | CCCN(CCC)[C@H]1CCc2c(OC)cccc2[C@H]1C.Cl | null | CHEMBL1122913 | J Med Chem | 1,985 | CHEMBL544195 | null | null | 0 | null | 5,909 | = | 1 | 0 | = | Accumulated counts/30 min | null | 8 | CHEMBL376 | Rattus norvegicus | Rattus norvegicus | 10116 | null | Accumulated counts/30 min | null | null | 8.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCN(CCC)[C@H]1CCc2c(OC)cccc2[C@H]1C.Cl |
RDKit 2D
21 21 0 0 0 0 0 0 0 0999 V2000
3.8893 2.1804 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 2.8580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2873 2.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.2873 1.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 1.2080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 1.6205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 2.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 2.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.1417 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.1417 1.6206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 1.2081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8561 2.8581 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.8561 3.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 4.0956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.5706 4.9206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.2851 2.8581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.9996 2.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0018 0.3830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.7163 -0.0295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4272 3.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 1 0
2 7 2 0
4 5 1 0
5 6 2 0
6 7 1 0
3 8 1 0
3 4 2 0
11 4 1 0
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12 13 1 0
12 14 1 0
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15 16 1 0
13 17 1 0
17 18 1 0
5 19 1 0
19 20 1 0
8 21 1 6
M END
> <chembl_id>
CHEMBL544195
> <chembl_pref_name>
None | InChI=1S/C18H29NO.ClH/c1-5-12-19(13-6-2)17-11-10-16-15(14(17)3)8-7-9-18(16)20-4;/h7-9,14,17H,5-6,10-13H2,1-4H3;1H/t14-,17+;/m1./s1 | ADVQBNGWEGSMGY-CVLQQERVSA-N | 4.24 | 1 | C18H30ClNO | 311.90 | 2 | 0 | 20 | 275.44 | 0.02 | 0 | 12.47 | 0.77 | N | 6 | CHEMBL157937 | CHEMBL544195 | CHEMBL157937 | null | null | null | null | Rattus norvegicus | null | null | 10,116 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Locomotor activity after reserpine pretreatment in rat | CHEMBL1122913 | Non-molecular target assigned | N | null | 1 | CHEMBL376 | null | null | null | Rattus norvegicus | Rattus norvegicus | false | ORGANISM | 10,116 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | The enantiomers of cis-5-hydroxy-1-methyl-2-(di-n-propylamino)tetralin and its methyl ether have been synthesized. The compounds were tested for central dopamine (DA) receptor activity, by using biochemical and behavioral tests in rats. The (1R,2S)-(-) enantiomers of 1 and 2 are characterized as centrally acting DA-receptor agonists while the corresponding (1S,2R)-(+) enantiomers are characterized as centrally acting DA-receptor antagonists. Compounds (+)-1 and (+)-2 differ from classical neuroleptics in being able to increase DA synthesis rate in a wide dose range without reducing locomotor activity, suggesting a pronounced selectivity for DA autoreceptors. Also the (-) enantiomers seem to act preferentially on DA autoreceptors. | Johansson AM, Arvidsson LE, Hacksell U, Nilsson JL, Svensson K, Hjorth S, Clark D, Carlsson A, Sanchez D, Andersson B. | 10.1021/jm00146a012 | null | 1049 | 8 | J Med Chem | null | 3,927,002 | 1 | Novel dopamine receptor agonists and antagonists with preferential action on autoreceptors. | 28 | 1,985 |
null | 38,129 | CHEMBL706332 | Tested in vitro against murine L1210 leukemia. | F | BAO_0000219 | cell-based format | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL542321 | null | 5.7 | 0 | http://www.openphacts.org/units/Nanomolar | 35,153 | = | 1 | 1 | = | IC50 | nM | 2,000 | CHEMBL386 | Mus musculus | L1210 | 10090 | null | IC50 | M | UO_0000065 | 0.000002 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
5.4623 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.0815 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3637 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7762 1.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.3637 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0488 1.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.0815 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7940 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7940 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.5262 2.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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-1.0613 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0829 -1.8058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.0613 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1822 2.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 -1.8058 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.6596 3.6219 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5085 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5085 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4810 3.5449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3155 4.3718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0633 -2.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0633 -3.0433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4922 -4.6933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7778 -4.2808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7778 -3.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2230 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2230 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7929 5.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9583 4.2178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4922 -5.5183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 1 0
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6 8 1 0
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21 31 1 0
25 32 1 0
M END
> <chembl_id>
CHEMBL542321
> <chembl_pref_name>
None | InChI=1S/C26H34N4O.ClH/c1-4-7-8-11-16-27-21-14-15-22-24-23(21)26(31)20-13-10-9-12-19(20)25(24)28-30(22)18-17-29(5-2)6-3;/h9-10,12-15,27H,4-8,11,16-18H2,1-3H3;1H | KJLHRQLQYPIDIX-UHFFFAOYSA-N | 5.58 | 3 | C26H35ClN4O | 455.05 | 5 | 1 | 31 | 418.59 | -0.89 | 1 | 50.16 | 0.32 | N | 11 | CHEMBL1191248 | CHEMBL542321 | CHEMBL1191248 | null | null | null | L1210 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308391 | Target assigned is non-molecular | 1 | Tested in vitro against murine L1210 leukemia. | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL386 | null | null | null | Mus musculus | L1210 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,130 | CHEMBL758597 | Optimal dose per injection in mg/kg required to inhibit growth of P388 leukemia cells in mice | F | BAO_0000218 | organism-based format | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL542321 | null | null | 0 | null | 35,153 | = | 1 | 1 | = | DOSE | mg.kg-1 | 200 | CHEMBL389 | Mus musculus | P388 | 10090 | null | Dose | mg kg-1 | UO_0000308 | 200.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
5.4623 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.0815 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3637 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7762 1.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.3637 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0488 1.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.0815 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7940 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7940 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.5262 2.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0613 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0829 -1.8058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.0613 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1822 2.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 -1.8058 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.6596 3.6219 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5085 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5085 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4810 3.5449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3155 4.3718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0633 -2.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0633 -3.0433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4922 -4.6933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7778 -4.2808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
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3.2230 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2230 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7929 5.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9583 4.2178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4922 -5.5183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 1 0
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6 8 1 0
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19 29 1 0
28 29 2 0
22 30 1 0
21 31 1 0
25 32 1 0
M END
> <chembl_id>
CHEMBL542321
> <chembl_pref_name>
None | InChI=1S/C26H34N4O.ClH/c1-4-7-8-11-16-27-21-14-15-22-24-23(21)26(31)20-13-10-9-12-19(20)25(24)28-30(22)18-17-29(5-2)6-3;/h9-10,12-15,27H,4-8,11,16-18H2,1-3H3;1H | KJLHRQLQYPIDIX-UHFFFAOYSA-N | 5.58 | 3 | C26H35ClN4O | 455.05 | 5 | 1 | 31 | 418.59 | -0.89 | 1 | 50.16 | 0.32 | N | 11 | CHEMBL1191248 | CHEMBL542321 | CHEMBL1191248 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000218 | organism-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Optimal dose per injection in mg/kg required to inhibit growth of P388 leukemia cells in mice | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,131 | CHEMBL762168 | Activity against P388 leukemia cells in mice, by intraperitoneal dosing and net log tumor cell kill was reported | F | BAO_0000219 | cell-based format | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL542321 | null | null | 0 | null | 35,153 | = | 1 | 0 | = | Activity | null | -1.4 | CHEMBL389 | Mus musculus | P388 | 10090 | null | Activity | null | null | -1.4 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
5.4623 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.0815 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3637 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7762 1.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
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25 32 1 0
M END
> <chembl_id>
CHEMBL542321
> <chembl_pref_name>
None | InChI=1S/C26H34N4O.ClH/c1-4-7-8-11-16-27-21-14-15-22-24-23(21)26(31)20-13-10-9-12-19(20)25(24)28-30(22)18-17-29(5-2)6-3;/h9-10,12-15,27H,4-8,11,16-18H2,1-3H3;1H | KJLHRQLQYPIDIX-UHFFFAOYSA-N | 5.58 | 3 | C26H35ClN4O | 455.05 | 5 | 1 | 31 | 418.59 | -0.89 | 1 | 50.16 | 0.32 | N | 11 | CHEMBL1191248 | CHEMBL542321 | CHEMBL1191248 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Activity against P388 leukemia cells in mice, by intraperitoneal dosing and net log tumor cell kill was reported | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,132 | CHEMBL759554 | Inhibition of P388 leukemia cells in mice, measured as percent treated to the control values with the number of 30 day survivors | F | BAO_0000219 | cell-based format | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL542321 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 35,153 | = | 1 | 0 | = | T/C | % | 110 | CHEMBL389 | Mus musculus | P388 | 10090 | null | T/C | % | UO_0000187 | 110.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | CCCCCCNc1ccc2c3c(nn2CCN(CC)CC)-c2ccccc2C(=O)c13.Cl |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
5.4623 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
1.0815 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3637 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7762 1.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.3637 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0488 1.5264 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.0815 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7940 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.7940 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.5262 2.1992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0613 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.0829 -1.8058 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-1.0613 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1822 2.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3488 -1.8058 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.6596 3.6219 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5085 0.6692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5085 -0.9808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4810 3.5449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.3155 4.3718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0633 -2.2183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.0633 -3.0433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4922 -4.6933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7778 -4.2808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7778 -3.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2230 -0.5683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.2230 0.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7929 5.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.9583 4.2178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.4922 -5.5183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 1 0
2 4 2 0
3 5 2 0
4 6 1 0
5 7 1 0
3 8 1 0
6 8 1 0
2 9 1 0
7 10 1 0
9 10 1 0
6 11 1 0
5 12 1 0
8 13 2 0
7 14 2 0
12 15 2 0
13 15 1 0
11 16 1 0
12 17 1 0
16 18 1 0
9 19 2 0
10 20 2 0
18 21 1 0
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17 23 1 0
23 24 1 0
25 26 1 0
24 27 1 0
26 27 1 0
20 28 1 0
19 29 1 0
28 29 2 0
22 30 1 0
21 31 1 0
25 32 1 0
M END
> <chembl_id>
CHEMBL542321
> <chembl_pref_name>
None | InChI=1S/C26H34N4O.ClH/c1-4-7-8-11-16-27-21-14-15-22-24-23(21)26(31)20-13-10-9-12-19(20)25(24)28-30(22)18-17-29(5-2)6-3;/h9-10,12-15,27H,4-8,11,16-18H2,1-3H3;1H | KJLHRQLQYPIDIX-UHFFFAOYSA-N | 5.58 | 3 | C26H35ClN4O | 455.05 | 5 | 1 | 31 | 418.59 | -0.89 | 1 | 50.16 | 0.32 | N | 11 | CHEMBL1191248 | CHEMBL542321 | CHEMBL1191248 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Inhibition of P388 leukemia cells in mice, measured as percent treated to the control values with the number of 30 day survivors | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,133 | CHEMBL706332 | Tested in vitro against murine L1210 leukemia. | F | BAO_0000219 | cell-based format | Br.CCN(CC)CCn1nc2c3c(c(NCCNC)ccc31)C(=O)c1c(O)ccc(O)c1-2 | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL543035 | null | 5.13 | 0 | http://www.openphacts.org/units/Nanomolar | 35,168 | = | 1 | 1 | = | IC50 | nM | 7,400 | CHEMBL386 | Mus musculus | L1210 | 10090 | null | IC50 | M | UO_0000065 | 0.0000074 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Br.CCN(CC)CCn1nc2c3c(c(NCCNC)ccc31)C(=O)c1c(O)ccc(O)c1-2 |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
8.5875 -2.1500 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.4500 -2.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9542 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4417 -1.8042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.9500 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9542 -3.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9500 -3.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4542 -3.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4500 -1.8000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.4542 -2.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9667 -1.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4667 -3.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -2.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -3.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -2.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4542 -4.1250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9667 -3.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9500 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9500 -3.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9625 -0.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4667 -4.1250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4792 -0.5875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -4.1500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -1.7875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.7792 -5.5500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4750 0.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0042 -0.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0417 -4.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2042 -5.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -6.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 0.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0042 -1.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 2 2 0
5 2 1 0
6 3 2 0
7 5 1 0
8 7 1 0
9 4 1 0
10 3 1 0
11 9 1 0
12 6 1 0
13 5 2 0
14 7 2 0
15 10 2 0
16 8 2 0
17 15 1 0
18 13 1 0
19 18 2 0
20 11 1 0
21 12 1 0
22 20 1 0
23 14 1 0
24 13 1 0
25 29 1 0
26 22 1 0
27 22 1 0
28 21 1 0
29 28 1 0
30 25 1 0
31 26 1 0
32 27 1 0
9 10 1 0
6 8 1 0
14 19 1 0
12 17 2 0
M END
> <chembl_id>
CHEMBL543035
> <chembl_pref_name>
None | InChI=1S/C23H29N5O3.BrH/c1-4-27(5-2)12-13-28-15-7-6-14(25-11-10-24-3)18-19(15)22(26-28)20-16(29)8-9-17(30)21(20)23(18)31;/h6-9,24-25,29-30H,4-5,10-13H2,1-3H3;1H | COCDUXBIESOLCR-UHFFFAOYSA-N | 2.63 | 3 | C23H30BrN5O3 | 504.43 | 8 | 4 | 31 | 423.52 | -0.47 | 0 | 102.65 | 0.24 | N | 9 | CHEMBL1191878 | CHEMBL543035 | CHEMBL1191878 | null | null | null | L1210 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308391 | Target assigned is non-molecular | 1 | Tested in vitro against murine L1210 leukemia. | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL386 | null | null | null | Mus musculus | L1210 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,134 | CHEMBL758597 | Optimal dose per injection in mg/kg required to inhibit growth of P388 leukemia cells in mice | F | BAO_0000218 | organism-based format | Br.CCN(CC)CCn1nc2c3c(c(NCCNC)ccc31)C(=O)c1c(O)ccc(O)c1-2 | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL543035 | null | null | 0 | null | 35,168 | = | 1 | 1 | = | DOSE | mg.kg-1 | 25 | CHEMBL389 | Mus musculus | P388 | 10090 | null | Dose | mg kg-1 | UO_0000308 | 25.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Br.CCN(CC)CCn1nc2c3c(c(NCCNC)ccc31)C(=O)c1c(O)ccc(O)c1-2 |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
8.5875 -2.1500 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.4500 -2.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9542 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4417 -1.8042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.9500 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9542 -3.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9500 -3.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4542 -3.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4500 -1.8000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.4542 -2.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9667 -1.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4667 -3.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -2.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -3.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -2.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4542 -4.1250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9667 -3.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9500 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9500 -3.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9625 -0.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4667 -4.1250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4792 -0.5875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -4.1500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -1.7875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.7792 -5.5500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4750 0.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0042 -0.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0417 -4.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2042 -5.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -6.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 0.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0042 -1.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 2 2 0
5 2 1 0
6 3 2 0
7 5 1 0
8 7 1 0
9 4 1 0
10 3 1 0
11 9 1 0
12 6 1 0
13 5 2 0
14 7 2 0
15 10 2 0
16 8 2 0
17 15 1 0
18 13 1 0
19 18 2 0
20 11 1 0
21 12 1 0
22 20 1 0
23 14 1 0
24 13 1 0
25 29 1 0
26 22 1 0
27 22 1 0
28 21 1 0
29 28 1 0
30 25 1 0
31 26 1 0
32 27 1 0
9 10 1 0
6 8 1 0
14 19 1 0
12 17 2 0
M END
> <chembl_id>
CHEMBL543035
> <chembl_pref_name>
None | InChI=1S/C23H29N5O3.BrH/c1-4-27(5-2)12-13-28-15-7-6-14(25-11-10-24-3)18-19(15)22(26-28)20-16(29)8-9-17(30)21(20)23(18)31;/h6-9,24-25,29-30H,4-5,10-13H2,1-3H3;1H | COCDUXBIESOLCR-UHFFFAOYSA-N | 2.63 | 3 | C23H30BrN5O3 | 504.43 | 8 | 4 | 31 | 423.52 | -0.47 | 0 | 102.65 | 0.24 | N | 9 | CHEMBL1191878 | CHEMBL543035 | CHEMBL1191878 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000218 | organism-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Optimal dose per injection in mg/kg required to inhibit growth of P388 leukemia cells in mice | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,136 | CHEMBL759554 | Inhibition of P388 leukemia cells in mice, measured as percent treated to the control values with the number of 30 day survivors | F | BAO_0000219 | cell-based format | Br.CCN(CC)CCn1nc2c3c(c(NCCNC)ccc31)C(=O)c1c(O)ccc(O)c1-2 | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL543035 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 35,168 | = | 1 | 0 | = | T/C | % | 219 | CHEMBL389 | Mus musculus | P388 | 10090 | null | T/C | % | UO_0000187 | 219.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Br.CCN(CC)CCn1nc2c3c(c(NCCNC)ccc31)C(=O)c1c(O)ccc(O)c1-2 |
RDKit 2D
32 34 0 0 0 0 0 0 0 0999 V2000
8.5875 -2.1500 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0
3.4500 -2.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9542 -2.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4417 -1.8042 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.9500 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9542 -3.2542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9500 -3.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4542 -3.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4500 -1.8000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.4542 -2.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9667 -1.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4667 -3.5417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -2.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -3.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 -2.6625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.4542 -4.1250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
4.9667 -3.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9500 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.9500 -3.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9625 -0.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.4667 -4.1250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4792 -0.5875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -4.1500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.4417 -1.7875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
3.7792 -5.5500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4750 0.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0042 -0.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.0417 -4.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.2042 -5.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.9417 -6.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.9542 0.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0042 -1.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3 2 1 0
4 2 2 0
5 2 1 0
6 3 2 0
7 5 1 0
8 7 1 0
9 4 1 0
10 3 1 0
11 9 1 0
12 6 1 0
13 5 2 0
14 7 2 0
15 10 2 0
16 8 2 0
17 15 1 0
18 13 1 0
19 18 2 0
20 11 1 0
21 12 1 0
22 20 1 0
23 14 1 0
24 13 1 0
25 29 1 0
26 22 1 0
27 22 1 0
28 21 1 0
29 28 1 0
30 25 1 0
31 26 1 0
32 27 1 0
9 10 1 0
6 8 1 0
14 19 1 0
12 17 2 0
M END
> <chembl_id>
CHEMBL543035
> <chembl_pref_name>
None | InChI=1S/C23H29N5O3.BrH/c1-4-27(5-2)12-13-28-15-7-6-14(25-11-10-24-3)18-19(15)22(26-28)20-16(29)8-9-17(30)21(20)23(18)31;/h6-9,24-25,29-30H,4-5,10-13H2,1-3H3;1H | COCDUXBIESOLCR-UHFFFAOYSA-N | 2.63 | 3 | C23H30BrN5O3 | 504.43 | 8 | 4 | 31 | 423.52 | -0.47 | 0 | 102.65 | 0.24 | N | 9 | CHEMBL1191878 | CHEMBL543035 | CHEMBL1191878 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Inhibition of P388 leukemia cells in mice, measured as percent treated to the control values with the number of 30 day survivors | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,137 | CHEMBL706332 | Tested in vitro against murine L1210 leukemia. | F | BAO_0000219 | cell-based format | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL545155 | null | 6.41 | 0 | http://www.openphacts.org/units/Nanomolar | 35,158 | = | 1 | 1 | = | IC50 | nM | 390 | CHEMBL386 | Mus musculus | L1210 | 10090 | null | IC50 | M | UO_0000065 | 3.9E-7 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 |
RDKit 2D
31 33 0 0 0 0 0 0 0 0999 V2000
5.0455 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3594 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4656 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6661 -1.4921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.9430 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -1.4921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2418 3.1087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.1421 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.3619 3.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -5.2046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7644 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -1.9046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -2.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0632 3.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -4.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.5405 3.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 2 0
2 4 1 0
3 6 1 0
5 7 1 0
4 8 2 0
5 8 1 0
2 9 1 0
7 9 1 0
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6 13 1 0
11 14 1 0
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10 19 2 0
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19 20 1 0
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13 24 1 0
17 24 1 0
11 25 1 0
23 25 2 0
14 26 1 0
18 27 1 0
26 27 1 0
18 28 1 0
17 29 1 0
22 30 1 0
28 30 1 0
21 31 1 0
29 31 1 0
M END
> <chembl_id>
CHEMBL545155
> <chembl_pref_name>
None | InChI=1S/C22H27N5O3.ClH/c28-13-10-23-7-8-25-17-5-1-3-15-19(17)22(30)16-4-2-6-18-20(16)21(15)26-27(18)12-9-24-11-14-29;/h1-6,23-25,28-29H,7-14H2;1H | HRMOIPHLLBLBBJ-UHFFFAOYSA-N | 0.82 | 3 | C22H28ClN5O3 | 445.95 | 8 | 5 | 30 | 409.49 | -0.66 | 0 | 111.44 | 0.23 | N | 11 | CHEMBL1193703 | CHEMBL545155 | CHEMBL1193703 | null | null | null | L1210 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308391 | Target assigned is non-molecular | 1 | Tested in vitro against murine L1210 leukemia. | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL386 | null | null | null | Mus musculus | L1210 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,138 | CHEMBL758597 | Optimal dose per injection in mg/kg required to inhibit growth of P388 leukemia cells in mice | F | BAO_0000218 | organism-based format | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL545155 | null | null | 0 | null | 35,158 | = | 1 | 1 | = | DOSE | mg.kg-1 | 12.5 | CHEMBL389 | Mus musculus | P388 | 10090 | null | Dose | mg kg-1 | UO_0000308 | 12.5 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 |
RDKit 2D
31 33 0 0 0 0 0 0 0 0999 V2000
5.0455 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3594 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4656 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6661 -1.4921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.9430 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -1.4921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2418 3.1087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.1421 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.3619 3.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -5.2046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7644 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -1.9046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -2.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0632 3.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -4.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.5405 3.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 2 0
2 4 1 0
3 6 1 0
5 7 1 0
4 8 2 0
5 8 1 0
2 9 1 0
7 9 1 0
4 10 1 0
6 10 1 0
7 11 2 0
5 12 2 0
6 13 1 0
11 14 1 0
8 15 1 0
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10 19 2 0
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13 24 1 0
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18 27 1 0
26 27 1 0
18 28 1 0
17 29 1 0
22 30 1 0
28 30 1 0
21 31 1 0
29 31 1 0
M END
> <chembl_id>
CHEMBL545155
> <chembl_pref_name>
None | InChI=1S/C22H27N5O3.ClH/c28-13-10-23-7-8-25-17-5-1-3-15-19(17)22(30)16-4-2-6-18-20(16)21(15)26-27(18)12-9-24-11-14-29;/h1-6,23-25,28-29H,7-14H2;1H | HRMOIPHLLBLBBJ-UHFFFAOYSA-N | 0.82 | 3 | C22H28ClN5O3 | 445.95 | 8 | 5 | 30 | 409.49 | -0.66 | 0 | 111.44 | 0.23 | N | 11 | CHEMBL1193703 | CHEMBL545155 | CHEMBL1193703 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000218 | organism-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Optimal dose per injection in mg/kg required to inhibit growth of P388 leukemia cells in mice | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,139 | CHEMBL762168 | Activity against P388 leukemia cells in mice, by intraperitoneal dosing and net log tumor cell kill was reported | F | BAO_0000219 | cell-based format | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL545155 | null | null | 0 | null | 35,158 | = | 1 | 0 | = | Activity | null | -0.3 | CHEMBL389 | Mus musculus | P388 | 10090 | null | Activity | null | null | -0.3 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 |
RDKit 2D
31 33 0 0 0 0 0 0 0 0999 V2000
5.0455 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3594 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4656 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6661 -1.4921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.9430 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -1.4921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2418 3.1087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.1421 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.3619 3.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -5.2046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7644 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -1.9046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -2.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0632 3.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -4.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.5405 3.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 2 0
2 4 1 0
3 6 1 0
5 7 1 0
4 8 2 0
5 8 1 0
2 9 1 0
7 9 1 0
4 10 1 0
6 10 1 0
7 11 2 0
5 12 2 0
6 13 1 0
11 14 1 0
8 15 1 0
9 16 2 0
10 19 2 0
15 20 2 0
19 20 1 0
16 23 1 0
13 24 1 0
17 24 1 0
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23 25 2 0
14 26 1 0
18 27 1 0
26 27 1 0
18 28 1 0
17 29 1 0
22 30 1 0
28 30 1 0
21 31 1 0
29 31 1 0
M END
> <chembl_id>
CHEMBL545155
> <chembl_pref_name>
None | InChI=1S/C22H27N5O3.ClH/c28-13-10-23-7-8-25-17-5-1-3-15-19(17)22(30)16-4-2-6-18-20(16)21(15)26-27(18)12-9-24-11-14-29;/h1-6,23-25,28-29H,7-14H2;1H | HRMOIPHLLBLBBJ-UHFFFAOYSA-N | 0.82 | 3 | C22H28ClN5O3 | 445.95 | 8 | 5 | 30 | 409.49 | -0.66 | 0 | 111.44 | 0.23 | N | 11 | CHEMBL1193703 | CHEMBL545155 | CHEMBL1193703 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Activity against P388 leukemia cells in mice, by intraperitoneal dosing and net log tumor cell kill was reported | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,140 | CHEMBL759554 | Inhibition of P388 leukemia cells in mice, measured as percent treated to the control values with the number of 30 day survivors | F | BAO_0000219 | cell-based format | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 | null | CHEMBL1123657 | J Med Chem | 1,987 | CHEMBL545155 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 35,158 | = | 1 | 0 | = | T/C | % | 133 | CHEMBL389 | Mus musculus | P388 | 10090 | null | T/C | % | UO_0000187 | 133.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | Cl.O=C1c2c(NCCNCCO)cccc2-c2nn(CCNCCO)c3cccc1c23 |
RDKit 2D
31 33 0 0 0 0 0 0 0 0999 V2000
5.0455 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.3594 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6648 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.4656 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0531 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6661 -1.4921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.9430 2.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 -1.4921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-0.7656 -0.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.0917 0.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-2.2418 3.1087 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.1421 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.4781 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-4.3619 3.6276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -5.2046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 0.5704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.7644 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.8062 -0.2546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -1.9046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.3773 -2.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.6628 -3.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.0632 3.0318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.0517 -4.3796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-3.5405 3.7046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 3 2 0
2 4 1 0
3 6 1 0
5 7 1 0
4 8 2 0
5 8 1 0
2 9 1 0
7 9 1 0
4 10 1 0
6 10 1 0
7 11 2 0
5 12 2 0
6 13 1 0
11 14 1 0
8 15 1 0
9 16 2 0
10 19 2 0
15 20 2 0
19 20 1 0
16 23 1 0
13 24 1 0
17 24 1 0
11 25 1 0
23 25 2 0
14 26 1 0
18 27 1 0
26 27 1 0
18 28 1 0
17 29 1 0
22 30 1 0
28 30 1 0
21 31 1 0
29 31 1 0
M END
> <chembl_id>
CHEMBL545155
> <chembl_pref_name>
None | InChI=1S/C22H27N5O3.ClH/c28-13-10-23-7-8-25-17-5-1-3-15-19(17)22(30)16-4-2-6-18-20(16)21(15)26-27(18)12-9-24-11-14-29;/h1-6,23-25,28-29H,7-14H2;1H | HRMOIPHLLBLBBJ-UHFFFAOYSA-N | 0.82 | 3 | C22H28ClN5O3 | 445.95 | 8 | 5 | 30 | 409.49 | -0.66 | 0 | 111.44 | 0.23 | N | 11 | CHEMBL1193703 | CHEMBL545155 | CHEMBL1193703 | null | null | null | P388 | Mus musculus | null | null | 10,090 | null | F | Functional | BAO_0000219 | cell-based format | CHEMBL3308401 | Target assigned is non-molecular | 1 | Inhibition of P388 leukemia cells in mice, measured as percent treated to the control values with the number of 30 day survivors | CHEMBL1123657 | Non-molecular target assigned | N | null | 1 | CHEMBL389 | null | null | null | Mus musculus | P388 | false | CELL-LINE | 10,090 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | Chromophore modification of the anthracenediones related to mitoxantrone in an attempt to provide agents with diminished or no cardiotoxicity has resulted in a novel class of DNA binders, the anthrapyrazoles. Their synthesis was carried out by a two-stage condensation sequence starting from requisite 1,4- or 1,5-dichloro-9,10-anthracenedione precursors. Reaction with a monoalkylhydrazine gave a chloroanthrapyrazole intermediate whose subsequent condensation with primary or secondary alkylamines provided the target "two-armed" anthrapyrazoles. A-ring 7,10-dihydroxy anthrapyrazoles were derived from amine condensation with intermediate 5-chloro-7,10-dihydroxyanthrapyrazoles or, alternatively, from intermediate 5-chloro-7,10-bis(benzyloxy)anthrapyrazoles followed by hydrogenolysis of the benzyl protecting groups to provide the target compounds. Potent in vitro activity was demonstrated against murine L1210 leukemia in vitro (IC50 = 10(-7)-10(-8) M) as well as against P388 leukemia in vivo over a wide range of structural variants. In general, activity against the P388 line was maximized by basic side chains at N-2 and C-5, two to three carbon spacers between proximal and distal nitrogens of the side chain, and A-ring hydroxylation. Besides having curative activity against the P388 line, the more active compounds were curative against murine B-16 melanoma in vivo. On the basis of their exceptional in vivo anticancer activity, A-ring dihydroxy compounds 71 and 74 reported in this study have been selected for development toward clinical trials. | Showalter HD, Johnson JL, Hoftiezer JM, Turner WR, Werbel LM, Leopold WR, Shillis JL, Jackson RC, Elslager EF. | 10.1021/jm00384a021 | null | 121 | 1 | J Med Chem | null | 3,806,589 | 1 | Anthrapyrazole anticancer agents. Synthesis and structure-activity relationships against murine leukemias. | 30 | 1,987 |
null | 38,141 | CHEMBL740648 | Nematocidal activity against Nematospiroides dubius induced necropsy in mouse, oral administration 200 mg/kg | F | BAO_0000218 | organism-based format | COc1ccc(N/C(=N/c2cccc(C3CN4CCSC4=N3)c2)SC)cc1 | null | CHEMBL1123619 | J Med Chem | 1,987 | CHEMBL54651 | null | null | 0 | http://qudt.org/vocab/unit#Percent | 91,483 | = | 1 | 0 | = | Reduction | % | 0 | CHEMBL612662 | Heligmosomoides polygyrus | Heligmosomoides polygyrus | 6339 | null | Reduction | % | UO_0000187 | 0.0 | null | null | null | null | -1 | 0 | -1 | null | null | -1 | null | Small molecule | 0 | false | false | 0 | null | -1 | MOL | false | false | null | null | false | COc1ccc(N/C(=N/c2cccc(C3CN4CCSC4=N3)c2)SC)cc1 |
RDKit 2D
27 30 0 0 0 0 0 0 0 0999 V2000
1.0667 -2.8125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.6917 -3.1750 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
1.0667 -2.0917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
5.4292 -3.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3167 -2.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.3167 -2.1000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0542 -2.8292 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.4417 -3.1750 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
4.8042 -2.8250 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.9375 -3.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5542 -2.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1750 -3.1875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.4292 -3.9125 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
6.6792 -3.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1708 -2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.1708 -2.8167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.9292 -3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.6750 -3.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.3042 -2.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.9292 -3.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7.3000 -4.2792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.5542 -4.2792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
2.9292 -3.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.5500 -4.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.1750 -3.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.8000 -4.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.5542 -5.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2 1 2 0
3 1 1 0
4 9 2 0
5 2 1 0
6 3 1 0
7 4 1 0
8 1 1 0
9 12 1 0
10 5 1 0
11 10 2 0
12 11 1 0
13 4 1 0
14 7 1 0
15 3 1 0
16 8 1 0
17 20 1 0
18 14 2 0
19 14 1 0
20 19 2 0
21 18 1 0
22 17 1 0
23 10 1 0
24 23 2 0
25 24 1 0
26 13 1 0
27 22 1 0
15 16 1 0
5 6 1 0
12 25 2 0
21 17 2 0
M END
> <chembl_id>
CHEMBL54651
> <chembl_pref_name>
None | InChI=1S/C20H22N4OS2/c1-25-17-8-6-15(7-9-17)21-19(26-2)22-16-5-3-4-14(12-16)18-13-24-10-11-27-20(24)23-18/h3-9,12,18H,10-11,13H2,1-2H3,(H,21,22) | COEWCKOZENJWDU-UHFFFAOYSA-N | 4.62 | 2 | C20H22N4OS2 | 398.56 | 6 | 1 | 27 | 398.56 | -0.95 | 0 | 49.22 | 0.6 | N | 4 | CHEMBL54651 | CHEMBL54651 | CHEMBL54651 | null | null | null | null | Heligmosomoides polygyrus | null | null | 6,339 | null | F | Functional | BAO_0000218 | organism-based format | null | Target assigned is non-molecular | 1 | Nematocidal activity against Nematospiroides dubius induced necropsy in mouse, oral administration 200 mg/kg | CHEMBL1123619 | Non-molecular target assigned | N | null | 1 | CHEMBL612662 | null | null | DOSE=200.0 mg/kg | ROUTE=None None | Heligmosomoides polygyrus | Heligmosomoides polygyrus | false | ORGANISM | 6,339 | null | null | null | null | 0 | null | null | null | null | null | null | null | null | null | null | null | A series of isothiourea derivatives of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (tetramisole) is described. The compounds are prepared by the S-alkylation of the thioureas that were obtained either by the reaction of an amine with 6-(3-isothiocyanatophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b] thiazole or by the reaction of an isothiocyanate with 6-(3-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole. These derivatives have an improved spectrum of activity over tetramisole and are active against nematodes, cestodes, and trematodes. The structure-activity relationships are discussed. | Brewer MD, Dorgan RJ, Manger BR, Mamalis P, Webster RA. | 10.1021/jm00393a028 | null | 1848 | 10 | J Med Chem | null | 3,116,256 | 1 | Isothiourea derivatives of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole with broad-spectrum anthelmintic activity. | 30 | 1,987 |
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