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The dataset generation failed because of a cast error
Error code: DatasetGenerationCastError
Exception: DatasetGenerationCastError
Message: An error occurred while generating the dataset
All the data files must have the same columns, but at some point there are 3 new columns ({'IUPAC Name', 'PubChem CID', 'Standardized SMILES'}) and 1 missing columns ({'IUPAC name'}).
This happened while the csv dataset builder was generating data using
zip://NMRBank_data_with_SMILES_156621_in_225809.csv::/tmp/hf-datasets-cache/medium/datasets/99996093384811-config-parquet-and-info-sweetssweets-NMRBank-cd81239d/hub/datasets--sweetssweets--NMRBank/snapshots/d9b8309cb1b27e0c2268007bfae0dd6d891d2aaf/NMRBank/NMRBank_data_with_SMILES_156621_in_225809.zip
Please either edit the data files to have matching columns, or separate them into different configurations (see docs at https://hf.co/docs/hub/datasets-manual-configuration#multiple-configurations)
Traceback: Traceback (most recent call last):
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/builder.py", line 1871, in _prepare_split_single
writer.write_table(table)
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/arrow_writer.py", line 623, in write_table
pa_table = table_cast(pa_table, self._schema)
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/table.py", line 2293, in table_cast
return cast_table_to_schema(table, schema)
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/table.py", line 2241, in cast_table_to_schema
raise CastError(
datasets.table.CastError: Couldn't cast
PMC accession number (PMCID): string
Paragraph: string
IUPAC Name: string
SMILES: string
1H NMR text: string
13C NMR text: string
1H NMR conditions: string
1H NMR chemical shifts: string
13C NMR conditions: string
13C NMR chemical shifts: string
Confidence in data given by large models: double
PMID: int64
Article Citation: string
Journal Name: string
Article publication time: double
License: string
LastUpdated (YYYY-MM-DD HH:MM:SS): string
Retracted: string
Standardized SMILES: string
PubChem CID: double
-- schema metadata --
pandas: '{"index_columns": [{"kind": "range", "name": null, "start": 0, "' + 2925
to
{'PMC accession number (PMCID)': Value(dtype='string', id=None), 'Paragraph': Value(dtype='string', id=None), 'IUPAC name': Value(dtype='string', id=None), 'SMILES': Value(dtype='string', id=None), '1H NMR text': Value(dtype='string', id=None), '13C NMR text': Value(dtype='string', id=None), '1H NMR conditions': Value(dtype='string', id=None), '1H NMR chemical shifts': Value(dtype='string', id=None), '13C NMR conditions': Value(dtype='string', id=None), '13C NMR chemical shifts': Value(dtype='string', id=None), 'Confidence in data given by large models': Value(dtype='float64', id=None), 'PMID': Value(dtype='int64', id=None), 'Article Citation': Value(dtype='string', id=None), 'Journal Name': Value(dtype='string', id=None), 'Article publication time': Value(dtype='float64', id=None), 'License': Value(dtype='string', id=None), 'LastUpdated (YYYY-MM-DD HH:MM:SS)': Value(dtype='string', id=None), 'Retracted': Value(dtype='string', id=None)}
because column names don't match
During handling of the above exception, another exception occurred:
Traceback (most recent call last):
File "/src/services/worker/src/worker/job_runners/config/parquet_and_info.py", line 1438, in compute_config_parquet_and_info_response
parquet_operations = convert_to_parquet(builder)
File "/src/services/worker/src/worker/job_runners/config/parquet_and_info.py", line 1050, in convert_to_parquet
builder.download_and_prepare(
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/builder.py", line 925, in download_and_prepare
self._download_and_prepare(
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/builder.py", line 1001, in _download_and_prepare
self._prepare_split(split_generator, **prepare_split_kwargs)
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/builder.py", line 1742, in _prepare_split
for job_id, done, content in self._prepare_split_single(
File "/src/services/worker/.venv/lib/python3.9/site-packages/datasets/builder.py", line 1873, in _prepare_split_single
raise DatasetGenerationCastError.from_cast_error(
datasets.exceptions.DatasetGenerationCastError: An error occurred while generating the dataset
All the data files must have the same columns, but at some point there are 3 new columns ({'IUPAC Name', 'PubChem CID', 'Standardized SMILES'}) and 1 missing columns ({'IUPAC name'}).
This happened while the csv dataset builder was generating data using
zip://NMRBank_data_with_SMILES_156621_in_225809.csv::/tmp/hf-datasets-cache/medium/datasets/99996093384811-config-parquet-and-info-sweetssweets-NMRBank-cd81239d/hub/datasets--sweetssweets--NMRBank/snapshots/d9b8309cb1b27e0c2268007bfae0dd6d891d2aaf/NMRBank/NMRBank_data_with_SMILES_156621_in_225809.zip
Please either edit the data files to have matching columns, or separate them into different configurations (see docs at https://hf.co/docs/hub/datasets-manual-configuration#multiple-configurations)Need help to make the dataset viewer work? Make sure to review how to configure the dataset viewer, and open a discussion for direct support.
PMC accession number (PMCID) string | Paragraph string | IUPAC name string | SMILES string | 1H NMR text string | 13C NMR text string | 1H NMR conditions string | 1H NMR chemical shifts string | 13C NMR conditions string | 13C NMR chemical shifts string | Confidence in data given by large models float64 | PMID int64 | Article Citation string | Journal Name string | Article publication time float64 | License string | LastUpdated (YYYY-MM-DD HH:MM:SS) string | Retracted string |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
PMC1073692 | 4-Amino-1-tert-butyl-3-phenylpyrazolo[3,4-d] pyrimidines (PP2 and hydroxy-PP) were synthesized according to Hanefeld et al.[32]. Benzyl bromide was used to protect the hydroxyl group for the hydroxy-PP synthesis. Hydrogenation (10% palladium on carbon) resulted in benzyl deprotection to yield hydroxy-PP. 4-Amino-1-tert... | hydroxy-PP | null | 1H NMR (400 MHz, DMSO-d6) δ 9.69 (brs), 8.22 (1H, s), 7.33 (1H, dd, J = 7.5, 7.5 Hz), 7.05 (2H, m), 6.86 (1H, dd, J = 7.5, 2 Hz), 5.74 (s), 1.73 (9H, s) | 13C NMR (100 MHz, DMSO-d6) δ 158.1 (s), 157.8 (s), 154.6 (d), 153.8 (s), 141.7 (s), 134.5 (s), 130.2 (d), 118.9 (d), 115.6 (d), 115.0 (d), 98.5 (s), 59.6 (s), 28.7 (q) | 400 MHz, DMSO-d6 | 9.69 (brs), 8.22 (1H, s), 7.33 (1H, dd, J = 7.5, 7.5 Hz), 7.05 (2H, m), 6.86 (1H, dd, J = 7.5, 2 Hz), 5.74 (s), 1.73 (9H, s) | 100 MHz, DMSO-d6 | 158.1, 157.8, 154.6, 153.8, 141.7, 134.5, 130.2, 118.9, 115.6, 115.0, 98.5, 59.6, 28.7 | 0.480605 | 15,799,708 | PLoS Biol. 2005 May 5; 3(5):e128 | PLoS Biol | 2,005 | CC BY | 2021-01-05 08:21:21 | no |
PMC1262691 | (1R, αR)-1, (1R, αS)-1, (1S, αR)-1, and (1S, αS)-1 (Figure 2) were prepared from the condensation of R-(+)- or S-(-)-α-methylbenzyl isocyanate ([α]20 D = +10° or -10°) with 1 equivalent of R-(+)- or S-(-)-1, 1'-bi-2-naphthol ([α]20 D = +34° or -34°) in the presence of a catalytic amount of pyridine in CH2Cl2 at 25°C fo... | (1R, αR)-1, (1R, αS)-1, (1S, αR)-1, and (1S, αS)-1 | null | 1H NMR (CDCl3, 300 MHz) δ/ppm 1.02 (d, J = 6.6 Hz, 3H, CH(Ph)CH3), 4.48 (quintet, J = 7 Hz, 1H, CH(Ph)CH3), 5.27 (d, J = 8.1 Hz, 1H, NH), 7.07–8.06 (m, 17H, aromatic H) | 13C NMR (CDCl3, 75.4 MHz) δ/ppm 21.88 (CH3), 50.36 (CH(Ph)CH3), 122.45, 123.51, 125.43, 125.69, 126.08, 126.48, 126.60, 127.10, 127.24, 127.91, 128.18, 128.37, 128.53, 129.40, 131.40, 133.30, 133.41, 142.98, and 147.20 (aromatic Cs), 153.91 (C = O) | CDCl3, 300 MHz | 1.02 (d, J = 6.6 Hz, 3H, CH(Ph)CH3), 4.48 (quintet, J = 7 Hz, 1H, CH(Ph)CH3), 5.27 (d, J = 8.1 Hz, 1H, NH), 7.07–8.06 (m, 17H, aromatic H) | CDCl3, 75.4 MHz | 21.88, 50.36, 122.45, 123.51, 125.43, 125.69, 126.08, 126.48, 126.60, 127.10, 127.24, 127.91, 128.18, 128.37, 128.53, 129.40, 131.40, 133.30, 133.41, 142.98, 147.20, 153.91 | 0.723557 | 16,176,589 | BMC Biochem. 2005 Sep 22; 6:17 | BMC Biochem | 2,005 | CC BY | 2021-01-04 16:26:24 | no |
PMC1274306 | Preparation of 7-(4-bromo-n-butoxy)naringenin (1) Naringenin (136 mg, 0.5 mmol, 1.0 eq) was dissolved in acetone (5 mL), then potassium carbonate (69 mg, 0.5 mmol, 1.0 eq) was added and heated to reflux for 30 minutes. To this suspension, 1,4-dibromobutane (107 mg, 0.5 mmol, 1.0 eq) was added and stirred at reflux for ... | 7-(4-bromo-n-butoxy)naringenin | O=C1CC(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)(OCCCCBr)=C3 | 1H NMR (acetone-d6, 250 MHz) δ 1.86–1.97 (m, 2H), 2.00–2.09 (m, 2H), 2.74 (dd, J = 17.0, 3.0 Hz, 1H), 3.19 (dd, J = 17.0, 12.8 Hz, 1H), 3.57 (t, J = 6.5 Hz, 2H), 4.11 (t, J = 6.3 Hz, 2H), 5.46 (d, J = 12.5 Hz, 1H), 6.03 (s, 1H), 6.04 (s, 1H), 6.89 (d, J = 8.3 Hz, 2H), 7.38 (d, J = 8.3 Hz, 2H), 8.48 (s, 1H), 12.11 (s, 1... | 13C NMR (acetone-d6, 62.9 MHz) δ 28.34, 30.18, 34.27, 43.46, 68.38, 79.98, 94.94, 95.88, 103.72, 116.17, 128.99, 130.67, 158.68, 164.15, 164.95, 168.09, 197.53 | acetone-d6, 250 MHz | 1.86–1.97 (m, 2H), 2.00–2.09 (m, 2H), 2.74 (dd, J = 17.0, 3.0 Hz, 1H), 3.19 (dd, J = 17.0, 12.8 Hz, 1H), 3.57 (t, J = 6.5 Hz, 2H), 4.11 (t, J = 6.3 Hz, 2H), 5.46 (d, J = 12.5 Hz, 1H), 6.03 (s, 1H), 6.04 (s, 1H), 6.89 (d, J = 8.3 Hz, 2H), 7.38 (d, J = 8.3 Hz, 2H), 8.48 (s, 1H), 12.11 (s, 1H) | acetone-d6, 62.9 MHz | 28.34, 30.18, 34.27, 43.46, 68.38, 79.98, 94.94, 95.88, 103.72, 116.17, 128.99, 130.67, 158.68, 164.15, 164.95, 168.09, 197.53 | 0.949671 | 16,216,122 | BMC Chem Biol. 2005 Oct 10; 5:3 | BMC Chem Biol | 2,005 | CC BY | 2021-01-04 16:30:50 | no |
PMC1310531 | Others < 5 The 13C NMR signals of C-4 and C-5 in the pyrimidine ring of cytidine (1) also showed 13C13C satellites. The quantitative analysis revealed the presence of a [4,5-13C2]-isotopolog at a molar abundance of 0.1 mol% (Fig. 2) which was significantly above the natural abundance level (0.01 mol%). Moreover, the 1H... | cytidine | OC[C@@H]1[C@H]([C@H]([C@H](N2C(N=C(C=C2)N)=O)O1)O)O | The 1H NMR signal of H-6 (Fig. 4) showed 13C coupling satellites indicating a 13C abundance of 1.2 mol% for the [6-13C1]-isotopolog, i.e. 0.1 mol% excess over the natural 13C abundance of 1.1 mol% (see filled circle in Fig. 2) | The 13C NMR signals of C-4 and C-5 in the pyrimidine ring of cytidine (1) also showed 13C13C satellites. The quantitative analysis revealed the presence of a [4,5-13C2]-isotopolog at a molar abundance of 0.1 mol% (Fig. 2) which was significantly above the natural abundance level (0.01 mol%). Moreover, the 1H NMR signal... | null | null | null | 4, 5 | 0.000458 | 16,285,881 | BMC Biochem. 2005 Nov 14; 6:24 | BMC Biochem | 2,005 | CC BY | 2021-01-04 16:26:24 | no |
PMC1310531 | The purine ring systems of adenosine and guanosine showed no significantly increased levels of molecular species carrying two or more 13C atoms (Table 1). 1H NMR analysis showed no increased 13C abundance for the position 8 methine groups of both nucleosides. Consequently, the data demonstrate that purines were obtaine... | alanine | N[C@@H](C)C(O)=O | null | The 13C NMR signals of alanine (4) were characterized by intense satellite signals due to couplings between adjacent 13C atoms. The signal for C-2 showed a doublet indicating coupling to 13C-3, as well as a double-doublet indicating simultaneous coupling to 13C-3 and 13C-1 | null | null | null | 2,3-13C2, U-13C3 | 0.002756 | 16,285,881 | BMC Biochem. 2005 Nov 14; 6:24 | BMC Biochem | 2,005 | CC BY | 2021-01-04 16:26:24 | no |
PMC1310531 | The 15N NMR spectrum showed a signal at 35.8 ppm which was assigned to [15N]phenylalanine by internal standardization. The 15N abundance was determined by 13C NMR spectroscopy. The 13C NMR signals for C-2 and C-3 were accompanied by up-field shifted satellite signals due to 15N isotope shifts. The sizes of the isotope ... | [15N]phenylalanine | null | null | The 13C NMR signals for C-2 and C-3 were accompanied by up-field shifted satellite signals due to 15N isotope shifts. The sizes of the isotope shifts for C-2 and C-3 (50.9 ppb and 37.6 ppb, respectively) as well as the 13C15N coupling constant of 3.7 Hz (1JCN) were in accordance with published values [5,6] | null | null | null | 50.9, 37.6, 3.7 | 0.092786 | 16,285,881 | BMC Biochem. 2005 Nov 14; 6:24 | BMC Biochem | 2,005 | CC BY | 2021-01-04 16:26:24 | no |
PMC1399459 | 3-Acetyl-5-nitrohexanoic acid methyl ester (2a) Purified by column chromatography (hexane/AcOEt, 7/3). 1H NMR (300 MHz, CDCl3) δ 1.55 (d, 3H, J = 6.7 Hz), 2.29 (s, 3H), 2.37–2.79 (2 m, 4 H), 2.92 (m, 1H), 3.67 (s, 3H), 4.55 (m, 1H); 13C NMR (75 MHz, CDCl3) δ 19.8, 29.8, 34.4, 36.2, 44.7, 52.0, 81.6, 171.4, 208.4. HRMS ... | 3-Acetyl-5-nitrohexanoic acid methyl ester | CC([N+]([O-])=O)CC(C(C)=O)CC(OC)=O | 1H NMR (300 MHz, CDCl3) δ 1.55 (d, 3H, J = 6.7 Hz), 2.29 (s, 3H), 2.37–2.79 (2 m, 4 H), 2.92 (m, 1H), 3.67 (s, 3H), 4.55 (m, 1H) | 13C NMR (75 MHz, CDCl3) δ 19.8, 29.8, 34.4, 36.2, 44.7, 52.0, 81.6, 171.4, 208.4 | 300 MHz, CDCl3 | 1.55 (d, 3H, J = 6.7 Hz), 2.29 (s, 3H), 2.37–2.79 (2 m, 4 H), 2.92 (m, 1H), 3.67 (s, 3H), 4.55 (m, 1H) | 75 MHz, CDCl3 | 19.8, 29.8, 34.4, 36.2, 44.7, 52.0, 81.6, 171.4, 208.4 | 0.941618 | 16,542,022 | Beilstein J Org Chem. 2005 Oct 7; 1:11 | Beilstein J Org Chem | 2,005 | CC BY | 2021-02-20 23:14:50 | no |
PMC1399459 | 3-Acetyl-5-oxohexanoic acid methyl ester (3a) Purified by column chromatography (hexane/AcOEt, 7/3). 1H NMR (300 MHz, CDCl3) δ 2.15 (s, 3H), 2.28 (s, 3H), 2.43; 2.65 (ABd, 2H, JAB = 16.5 Hz, JA-H = 7 Hz, JB-H = 6.6 Hz), 2.60; 2.93 (ABd, 2H, JAB = 18.1 Hz, JA-H = 8 Hz, JB-H = 5.5 Hz), 3.36 (m, 1H), 3.67 (s, 3H); 13C NMR... | 3-Acetyl-5-oxohexanoic acid methyl ester | CC(CC(C(C)=O)CC(OC)=O)=O | 1H NMR (300 MHz, CDCl3) δ 2.15 (s, 3H), 2.28 (s, 3H), 2.43; 2.65 (ABd, 2H, JAB = 16.5 Hz, JA-H = 7 Hz, JB-H = 6.6 Hz), 2.60; 2.93 (ABd, 2H, JAB = 18.1 Hz, JA-H = 8 Hz, JB-H = 5.5 Hz), 3.36 (m, 1H), 3.67 (s, 3H) | 13C NMR (75 MHz, CDCl3) δ 29.2, 29.8, 35.0, 42.9, 44.4, 51.9, 172.0, 206.2, 209.5 | 300 MHz, CDCl3 | 2.15 (s, 3H), 2.28 (s, 3H), 2.43; 2.65 (ABd, 2H, JAB = 16.5 Hz, JA-H = 7 Hz, JB-H = 6.6 Hz), 2.60; 2.93 (ABd, 2H, JAB = 18.1 Hz, JA-H = 8 Hz, JB-H = 5.5 Hz), 3.36 (m, 1H), 3.67 (s, 3H) | 75 MHz, CDCl3 | 29.2, 29.8, 35.0, 42.9, 44.4, 51.9, 172.0, 206.2, 209.5 | 0.901676 | 16,542,022 | Beilstein J Org Chem. 2005 Oct 7; 1:11 | Beilstein J Org Chem | 2,005 | CC BY | 2021-02-20 23:14:50 | no |
PMC1399459 | 4-Benzyl-3-methylcyclopent-2-enone (4d) Purified by column chromatography (hexane/AcOEt, 8/2). 1H NMR (300 MHz, CDCl3) δ 2.09 (s, 3H), 2.26–2.59 (m, 2H), 2.71 (m, 1H), 3.21 (m, 2H), 5.92 (s, 1H), 7.17–7.28 (m, 5H); 13C NMR (75 MHz, CDCl3) δ 19.4, 37.0, 39.0, 48.0, 126.3, 128.4, 128.8, 129.8, 139.6, 177.6, 211.0. HRMS C... | 4-Benzyl-3-methylcyclopent-2-enone | CC(C(CC1=CC=CC=C1)C2)=CC2=O | 1H NMR (300 MHz, CDCl3) δ 2.09 (s, 3H), 2.26–2.59 (m, 2H), 2.71 (m, 1H), 3.21 (m, 2H), 5.92 (s, 1H), 7.17–7.28 (m, 5H) | 13C NMR (75 MHz, CDCl3) δ 19.4, 37.0, 39.0, 48.0, 126.3, 128.4, 128.8, 129.8, 139.6, 177.6, 211.0 | 300 MHz, CDCl3 | 2.09 (s, 3H), 2.26–2.59 (m, 2H), 2.71 (m, 1H), 3.21 (m, 2H), 5.92 (s, 1H), 7.17–7.28 (m, 5H) | 75 MHz, CDCl3 | 19.4, 37.0, 39.0, 48.0, 126.3, 128.4, 128.8, 129.8, 139.6, 177.6, 211.0 | 0.970725 | 16,542,022 | Beilstein J Org Chem. 2005 Oct 7; 1:11 | Beilstein J Org Chem | 2,005 | CC BY | 2021-02-20 23:14:50 | no |
PMC1479381 | Experimental 2- [2-(2-Bromoethoxy)-2-oxoethyl]-5-nitrobenzoic acid (3a) (66% yield) Tan crystals: mp 113–115°C (lit. [25] 90°C);1H NMR: δ 3.50 (t, 2H, J = 5.96 Hz) 4.21 (s, 2H) 4.43 (t, 2H, J = 6.06 Hz) 7.51 (d, 1H, J = 8.34 Hz) 8.39 (dd, 1H, J = 2.59 Hz, 8.39 Hz) 8.98 (d, J = 2.39 Hz);13C NMR: δ 28.40, 40.13, 64.17, 1... | 2- [2-(2-Bromoethoxy)-2-oxoethyl]-5-nitrobenzoic acid | O=C(O)C1=CC([N+]([O-])=O)=CC=C1CC(OCCBr)=O | 1H NMR: δ 3.50 (t, 2H, J = 5.96 Hz) 4.21 (s, 2H) 4.43 (t, 2H, J = 6.06 Hz) 7.51 (d, 1H, J = 8.34 Hz) 8.39 (dd, 1H, J = 2.59 Hz, 8.39 Hz) 8.98 (d, J = 2.39 Hz) | 13C NMR: δ 28.40, 40.13, 64.17, 126.24, 126.45, 130.97, 133.32, 142.59, 146.84, 167.46, 169.63 | null | 3.50 (t, 2H, J = 5.96 Hz), 4.21 (s, 2H), 4.43 (t, 2H, J = 6.06 Hz), 7.51 (d, 1H, J = 8.34 Hz), 8.39 (dd, 1H, J = 2.59 Hz, 8.39 Hz), 8.98 (d, J = 2.39 Hz) | null | 28.40, 40.13, 64.17, 126.24, 126.45, 130.97, 133.32, 142.59, 146.84, 167.46, 169.63 | 0.60075 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [2-(3-Bromopropoxy)-2-oxoethyl]-5-nitrobenzoic acid (3b) (51% yield) White crystals: mp 122–123°C; 1H NMR: δ 2.19 (m, 2H) 3.44 (t, 2H, J = 6.56 Hz) 4.18 (s, 2H) 4.28 (t, 2H, J = 5.96 Hz) 7.51 (d, 1H, J = 8.34 Hz) 8.39 (dd, 1H, J = 2.39 Hz, 8.35 Hz) 8.98 (d, 1H, J = 2.18 Hz) 9.78 (br s, 1H); 13C NMR: δ 29.18, 31.58, ... | 2- [2-(3-Bromopropoxy)-2-oxoethyl]-5-nitrobenzoic acid | O=C(O)C1=CC([N+]([O-])=O)=CC=C1CC(OCCCBr)=O | 1H NMR: δ 2.19 (m, 2H) 3.44 (t, 2H, J = 6.56 Hz) 4.18 (s, 2H) 4.28 (t, 2H, J = 5.96 Hz) 7.51 (d, 1H, J = 8.34 Hz) 8.39 (dd, 1H, J = 2.39 Hz, 8.35 Hz) 8.98 (d, 1H, J = 2.18 Hz) 9.78 (br s, 1H) | 13C NMR: δ 29.18, 31.58, 40.51, 63.12, 126.84, 127.52, 129.77, 143.37, 147.47, 169.92, 170.05 | null | 2.19 (m, 2H), 3.44 (t, 2H, J = 6.56 Hz), 4.18 (s, 2H), 4.28 (t, 2H, J = 5.96 Hz), 7.51 (d, 1H, J = 8.34 Hz), 8.39 (dd, 1H, J = 2.39 Hz, 8.35 Hz), 8.98 (d, 1H, J = 2.18 Hz), 9.78 (br s, 1H) | null | 29.18, 31.58, 40.51, 63.12, 126.84, 127.52, 129.77, 143.37, 147.47, 169.92, 170.05 | 0.567413 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [2-(2-Bromoethoxy)-2-oxoethyl]benzoic acid (3c) (50% yield) Tan crystals: mp 82–83°C; 1H NMR: δ 3.50 (t, 2H, J = 6.25 Hz) 4.07 (s, 2H) 4.40 (t, 2H, J = 6.25 Hz) 7.27 (d, 1H, J = 7.75 Hz) 7.45 (t, 1H, J = 7.55 Hz) 7.54 (td, 1H, J = 1.39 Hz, 7.55 Hz) 8.14 (d, 1H, J = 7.74 Hz); 13C NMR: δ 28.50, 40.68, 64.08, 127.65, 1... | 2- [2-(2-Bromoethoxy)-2-oxoethyl]benzoic acid | O=C(O)C1=CC=CC=C1CC(OCCBr)=O | 1H NMR: δ 3.50 (t, 2H, J = 6.25 Hz) 4.07 (s, 2H) 4.40 (t, 2H, J = 6.25 Hz) 7.27 (d, 1H, J = 7.75 Hz) 7.45 (t, 1H, J = 7.55 Hz) 7.54 (td, 1H, J = 1.39 Hz, 7.55 Hz) 8.14 (d, 1H, J = 7.74 Hz) | 13C NMR: δ 28.50, 40.68, 64.08, 127.65, 128.32, 131.95, 132.43, 133.35, 136.40, 170.86, 172.43 | null | 3.50 (t, 2H, J = 6.25 Hz), 4.07 (s, 2H), 4.40 (t, 2H, J = 6.25 Hz), 7.27 (d, 1H, J = 7.75 Hz), 7.45 (t, 1H, J = 7.55 Hz), 7.54 (td, 1H, J = 1.39 Hz, 7.55 Hz), 8.14 (d, 1H, J = 7.74 Hz) | null | 28.50, 40.68, 64.08, 127.65, 128.32, 131.95, 132.43, 133.35, 136.40, 170.86, 172.43 | 0.63667 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [2-(3-Bromopropoxy)-2-oxoethyl]benzoic acid (3d) (70% yield) White crystals: mp 79–80°C; 1H NMR: δ 2.16 (m, 2H, J = 6.31 Hz) 3.42 (t, 2H, J = 6.55 Hz) 4.05 (s, 2H) 4.24 (t, 2H, J = 5.96 Hz) 7.27 (d, 1H, J = 7.55 Hz) 7.40 (t, 1H, J = 7.65 Hz) 7.54 (td, 1H, J = 1.2, 7.35 Hz) 8.14 (dd, 1H, J = 0.99, 7.74 Hz); 13C NMR: ... | 2- [2-(3-Bromopropoxy)-2-oxoethyl]benzoic acid | O=C(O)C1=CC=CC=C1CC(OCCCBr)=O | 1H NMR: δ 2.16 (m, 2H, J = 6.31 Hz) 3.42 (t, 2H, J = 6.55 Hz) 4.05 (s, 2H) 4.24 (t, 2H, J = 5.96 Hz) 7.27 (d, 1H, J = 7.55 Hz) 7.40 (t, 1H, J = 7.65 Hz) 7.54 (td, 1H, J = 1.2, 7.35 Hz) 8.14 (dd, 1H, J = 0.99, 7.74 Hz) | 13C NMR: δ 29.50, 31.80, 40.80, 62.52, 127.60, 128.35, 131.91, 132.41, 133.35, 136.86, 171.17, 172.47 | null | 2.16 (m, 2H, J = 6.31 Hz), 3.42 (t, 2H, J = 6.55 Hz), 4.05 (s, 2H), 4.24 (t, 2H, J = 5.96 Hz), 7.27 (d, 1H, J = 7.55 Hz), 7.40 (t, 1H, J = 7.65 Hz), 7.54 (td, 1H, J = 1.2, 7.35 Hz), 8.14 (dd, 1H, J = 0.99, 7.74 Hz) | null | 29.50, 31.80, 40.80, 62.52, 127.60, 128.35, 131.91, 132.41, 133.35, 136.86, 171.17, 172.47 | 0.436206 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [2-(4-Bromobutoxy)-2-oxoethyl]benzoic acid (3e) A solution of 4-bromo-1-butanol (2e, 6.0 mL, 41.6 mmol), homophthalic acid (1c, 2.5 g, 13.8 mmol), and five drops of concentrated sulfuric acid was refluxed in benzene (50 mL) for four hours. The solution was cooled and washed with water (2 × 25 mL), brine (1 × 25 mL),... | 2- [2-(4-Bromobutoxy)-2-oxoethyl]benzoic acid | O=C(O)C1=CC=CC=C1CC(OCCCCBr)=O | 1H NMR: δ 1.79 (m, 2H) 1.87 (m, 2H) 3.38 (t, 2H, J = 6.45 Hz) 4.04 (s, 2H) 4.13 (t, 2H, J = 6.15 Hz) 7.27 (d, 1H, J = 7.55 Hz) 7.39 (t, 2H, J = 7.65 Hz) 7.54 (td, 1H, J = 1.4, 7.55 Hz) 8.13 (dd, 1H, J = 1.19, 7.74 Hz) | 13C NMR: δ 27.33, 29.32, 33.19, 63.85, 127.56, 128.41, 131.88, 132.42, 133.33, 136.77, 171.32, 172.58 | null | 1.79 (m, 2H), 1.87 (m, 2H), 3.38 (t, 2H, J = 6.45 Hz), 4.04 (s, 2H), 4.13 (t, 2H, J = 6.15 Hz), 7.27 (d, 1H, J = 7.55 Hz), 7.39 (t, 2H, J = 7.65 Hz), 7.54 (td, 1H, J = 1.4, 7.55 Hz), 8.13 (dd, 1H, J = 1.19, 7.74 Hz) | null | 27.33, 29.32, 33.19, 63.85, 127.56, 128.41, 131.88, 132.42, 133.33, 136.77, 171.32, 172.58 | 0.496514 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(2-Bromoethoxy)-4-chloro-7-nitro-1H-isochromen-1-one (4a) (43% yield) Yellow crystals: mp 126–128°C (lit. [25] 120°C); 1H NMR: δ 3.67 (t, 2H, J = 6.16 Hz) 4.74 (t, 2H, J = 6.06 Hz) 7.86 (d, 1H, J = 8.94 Hz) 8.53 (dd, 1H, J = 2.39 Hz, 8.94 Hz) 9.03 (d, 1H, J = 2.38 Hz); 13C NMR: δ 27.72, 69.63, 90.86, 117.17, 123.81, ... | 3-(2-Bromoethoxy)-4-chloro-7-nitro-1H-isochromen-1-one | O=C1C2=C(C=CC([N+]([O-])=O)=C2)C(Cl)=C(OCCBr)O1 | 1H NMR: δ 3.67 (t, 2H, J = 6.16 Hz) 4.74 (t, 2H, J = 6.06 Hz) 7.86 (d, 1H, J = 8.94 Hz) 8.53 (dd, 1H, J = 2.39 Hz, 8.94 Hz) 9.03 (d, 1H, J = 2.38 Hz) | 13C NMR: δ 27.72, 69.63, 90.86, 117.17, 123.81, 126.32, 129.82, 142.71, 145.47, 154.77, 157.06 | null | 3.67 (t, 2H, J = 6.16 Hz), 4.74 (t, 2H, J = 6.06 Hz), 7.86 (d, 1H, J = 8.94 Hz), 8.53 (dd, 1H, J = 2.39 Hz, 8.94 Hz), 9.03 (d, 1H, J = 2.38 Hz) | null | 27.72, 69.63, 90.86, 117.17, 123.81, 126.32, 129.82, 142.71, 145.47, 154.77, 157.06 | 0.680596 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(3-Bromopropoxy)-4-chloro-7-nitro-1H-isochromen-1-one (4b) (76% yield) Pale yellow crystals: mp 131–134°C; 1H NMR: δ 2.37 (m, 2H) 3.59 (t, 2H, J = 6.26 Hz) 4.61 (t, 2H, J = 5.86 Hz) 7.81 (d, 1H, J = 8.94 Hz) 8.50 (dd, 1H, J = 2.09 Hz, 8.84 Hz) 8.99 (d, 1H, J = 1.79 Hz); 13C NMR: δ 28.49, 31.92, 68.56, 90.46, 116.93, ... | 3-(3-Bromopropoxy)-4-chloro-7-nitro-1H-isochromen-1-one | O=C1C2=C(C=CC([N+]([O-])=O)=C2)C(Cl)=C(OCCCBr)O1 | 1H NMR: δ 2.37 (m, 2H) 3.59 (t, 2H, J = 6.26 Hz) 4.61 (t, 2H, J = 5.86 Hz) 7.81 (d, 1H, J = 8.94 Hz) 8.50 (dd, 1H, J = 2.09 Hz, 8.84 Hz) 8.99 (d, 1H, J = 1.79 Hz) | 13C NMR: δ 28.49, 31.92, 68.56, 90.46, 116.93, 123.52, 126.22, 129.68, 142.77, 145.77, 155.34, 157.18 | null | 2.37 (m, 2H), 3.59 (t, 2H, J = 6.26 Hz), 4.61 (t, 2H, J = 5.86 Hz), 7.81 (d, 1H, J = 8.94 Hz), 8.50 (dd, 1H, J = 2.09 Hz, 8.84 Hz), 8.99 (d, 1H, J = 1.79 Hz) | null | 28.49, 31.92, 68.56, 90.46, 116.93, 123.52, 126.22, 129.68, 142.77, 145.77, 155.34, 157.18 | 0.616141 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(2-Bromoethoxy)-4-chloro-1H-isochromen-1-one (4c) (30% yield) Yellow solid: mp 81–82°C; 1H NMR: δ 3.65 (t, 2H, J = 6.35 Hz) 4.64 (t, 2H, J = 6.35 Hz) 7.41 (t, 1H, J = 7.15 Hz) 7.74 (m, 2H) 8.20 (d, 1H, J = 7.75 Hz); 13C NMR: δ 28.07, 69.37, 92.09, 117.53, 122.47, 126.55, 130.06, 135.62, 137.35, 152.08, 159.01. | 3-(2-Bromoethoxy)-4-chloro-1H-isochromen-1-one | O=C1C2=C(C=CC=C2)C(Cl)=C(OCCBr)O1 | 1H NMR: δ 3.65 (t, 2H, J = 6.35 Hz) 4.64 (t, 2H, J = 6.35 Hz) 7.41 (t, 1H, J = 7.15 Hz) 7.74 (m, 2H) 8.20 (d, 1H, J = 7.75 Hz) | 13C NMR: δ 28.07, 69.37, 92.09, 117.53, 122.47, 126.55, 130.06, 135.62, 137.35, 152.08, 159.01 | null | 3.65 (t, 2H, J = 6.35 Hz), 4.64 (t, 2H, J = 6.35 Hz), 7.41 (t, 1H, J = 7.15 Hz), 7.74 (m, 2H), 8.20 (d, 1H, J = 7.75 Hz) | null | 28.07, 69.37, 92.09, 117.53, 122.47, 126.55, 130.06, 135.62, 137.35, 152.08, 159.01 | 0.664702 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(3-Bromopropoxy)-4-chloro-1H-isochromen-1-one (4d) (53% yield) Yellow crystals: mp 95–97°C; 1H NMR: δ 2.33 (m, 2H) 3.60 (t, 2H, J = 6.35 Hz) 4.51 (t, 2H, J = 5.76 Hz) 7.40 (t, 1H, J = 6.75 Hz) 7.72 (m, 2H) 8.19 (d, 1H, J = 7.94 Hz); 13C NMR: δ 28.88, 32.26, 68.28, 91.91, 117.58, 122.39, 126.43, 130.12, 135.62, 137.57... | 3-(3-Bromopropoxy)-4-chloro-1H-isochromen-1-one | O=C1C2=C(C=CC=C2)C(Cl)=C(OCCCBr)O1 | 1H NMR: δ 2.33 (m, 2H) 3.60 (t, 2H, J = 6.35 Hz) 4.51 (t, 2H, J = 5.76 Hz) 7.40 (t, 1H, J = 6.75 Hz) 7.72 (m, 2H) 8.19 (d, 1H, J = 7.94 Hz) | 13C NMR: δ 28.88, 32.26, 68.28, 91.91, 117.58, 122.39, 126.43, 130.12, 135.62, 137.57, 152.74, 159.33 | null | 2.33 (m, 2H), 3.60 (t, 2H, J = 6.35 Hz), 4.51 (t, 2H, J = 5.76 Hz), 7.40 (t, 1H, J = 6.75 Hz), 7.72 (m, 2H), 8.19 (d, 1H, J = 7.94 Hz) | null | 28.88, 32.26, 68.28, 91.91, 117.58, 122.39, 126.43, 130.12, 135.62, 137.57, 152.74, 159.33 | 0.621532 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(4-Bromobutoxy)-4-chloro-1H-isochromen-1-one (4e) A solution of 3e (0.75 g, 2.3 mmol) and phosphorus pentachloride (1.23 g, 5.9 mmol) was refluxed in benzene (50 mL) for fourteen hours. The orange solution was cooled, washed with water (2 × 25 mL), saturated sodium bicarbonate (2 × 15 mL), brine (1 × 25 mL), and drie... | 3-(4-Bromobutoxy)-4-chloro-1H-isochromen-1-one | O=C1C2=C(C=CC=C2)C(Cl)=C(OCCCCBr)O1 | 1H NMR: δ 1.98 (m, 2H) 2.06 (m, 2H) 3.48 (t, 2H, J = 6.25 Hz) 4.40 (t, 2H, J = 5.96 Hz) 7.38 (td, 1H, J = 1.59 Hz, 7.50 Hz) 7.70 (m, 2H) 8.17 (d, 1H, J = 7.55 Hz) | 13C NMR: δ 27.33, 29.32, 33.12, 40.80, 63.81, 127.55, 128.41. 131.86, 132.38, 133.30, 136.76, 171.26, 172.29 | null | 1.98 (m, 2H), 2.06 (m, 2H), 3.48 (t, 2H, J = 6.25 Hz), 4.40 (t, 2H, J = 5.96 Hz), 7.38 (td, 1H, J = 1.59 Hz, 7.50 Hz), 7.70 (m, 2H), 8.17 (d, 1H, J = 7.55 Hz) | null | 27.33, 29.32, 33.12, 40.80, 63.81, 127.55, 128.41, 131.86, 132.38, 133.30, 136.76, 171.26, 172.29 | 0.399901 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [2-(4-Chloro-1-oxo-1H-isochromen-3-yloxy)ethyl]isothiourea hydrobromide (5c) (64% yield) Yellow solid: mp 168–170°C (lit. [24] 167–169°C); 1H NMR: (DMSO-d6) δ 3.65 (t, 2H, J = 5.66 Hz) 4.58 (t, 2H, J = 5.67 Hz) 7.53 (t, 1H, J = 7.65 Hz) 7.69 (d, 1H, J = 8.14 Hz) 7.92 (t, 1H, J = 7.05 Hz) 8.13 (d, 1H, J = 7.75 Hz) 9.... | 2- [2-(4-Chloro-1-oxo-1H-isochromen-3-yloxy)ethyl]isothiourea hydrobromide | N=C(N)SCCOC(OC1=O)=C(Cl)C2=C1C=CC=C2.[H]Br | 1H NMR: (DMSO-d6) δ 3.65 (t, 2H, J = 5.66 Hz) 4.58 (t, 2H, J = 5.67 Hz) 7.53 (t, 1H, J = 7.65 Hz) 7.69 (d, 1H, J = 8.14 Hz) 7.92 (t, 1H, J = 7.05 Hz) 8.13 (d, 1H, J = 7.75 Hz) 9.15 (br s, 4H) | 13C NMR: δ 29.73, 68.11, 90.48, 117.18, 121.72, 126.70, 129.48, 135.99, 136.56, 152.18, 158.35, 169.11 | DMSO-d6 | 3.65 (t, 2H, J = 5.66 Hz), 4.58 (t, 2H, J = 5.67 Hz), 7.53 (t, 1H, J = 7.65 Hz), 7.69 (d, 1H, J = 8.14 Hz), 7.92 (t, 1H, J = 7.05 Hz), 8.13 (d, 1H, J = 7.75 Hz), 9.15 (br s, 4H) | null | 29.73, 68.11, 90.48, 117.18, 121.72, 126.70, 129.48, 135.99, 136.56, 152.18, 158.35, 169.11 | 0.607368 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [3-(4-Chloro-1-oxo-1H-isochromen-3-yloxy)propyl]isothiourea hydrobromide (5d) (40% yield) Yellow solid: mp 159–163°C (lit. [24] 165–167°C);1H NMR: (DMSO-d6) 2.21 (m, 2H) 3.40 (t, 2H, J = 7.18 Hz) 4.55 (t, 2H, J = 6.11 Hz) 7.62 (td, 1H, J = 0.95, 7.60 Hz) 7.79 (d, 1H, J = 7.70 Hz) 8.02 (td, 1H, J = 1.23, 7.70 Hz) 8.2... | 2- [3-(4-Chloro-1-oxo-1H-isochromen-3-yloxy)propyl]isothiourea hydrobromide | N=C(N)SCCCOC(OC1=O)=C(Cl)C2=C1C=CC=C2.[H]Br | 1H NMR: (DMSO-d6) 2.21 (m, 2H) 3.40 (t, 2H, J = 7.18 Hz) 4.55 (t, 2H, J = 6.11 Hz) 7.62 (td, 1H, J = 0.95, 7.60 Hz) 7.79 (d, 1H, J = 7.70 Hz) 8.02 (td, 1H, J = 1.23, 7.70 Hz) 8.23 (dd, 1H, J = 1.25, 7.50 Hz) 10.09 (br s, 4H) | 13C NMR: δ 26.66, 28.53, 68.68, 90.43, 117.13, 121.66, 126.59, 129.47, 135.96, 136.66, 152.63, 158.53, 169.36 | DMSO-d6 | 2.21 (m, 2H), 3.40 (t, 2H, J = 7.18 Hz), 4.55 (t, 2H, J = 6.11 Hz), 7.62 (td, 1H, J = 0.95, 7.60 Hz), 7.79 (d, 1H, J = 7.70 Hz), 8.02 (td, 1H, J = 1.23, 7.70 Hz), 8.23 (dd, 1H, J = 1.25, 7.50 Hz), 10.09 (br s, 4H) | null | 26.66, 28.53, 68.68, 90.43, 117.13, 121.66, 126.59, 129.47, 135.96, 136.66, 152.63, 158.53, 169.36 | 0.599596 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [4-(4-Chloro-1-oxo-1H-isochromen-3-yloxy)butyl]isothiourea hydrobromide (5e) A solution of 4e (0.25 g, 0.75 mmol) and thiourea (0.075 g, 0.98 mmol) in dry tetrahydrofuran (25 mL) was refluxed for forty-eight hours. The resulting pale yellow solid was filtered and washed with hot tetrahydrofuran (3 × 10 mL) to give 0... | 2- [4-(4-Chloro-1-oxo-1H-isochromen-3-yloxy)butyl]isothiourea hydrobromide | N=C(N)SCCCCOC(OC1=O)=C(Cl)C2=C1C=CC=C2.[H]Br | 1H NMR: (DMSO-d6) δ 1.82 (br s, 4H) 3.24 (t, 2H, J = 6.45 Hz) 4.39 (t, 2H, J = 5.75 Hz) 7.50 (t, 1H, J = 7.45 Hz) 7.65 (d, 1H, 7.45 Hz) 7.89 (t, 1H, J = 7.25 Hz) 8.09 (d, 1H, J = 7.75 Hz) 9.07 (br s, 4H) | 13C NMR: δ 24.92, 27.35, 29.59, 69.96, 90.20, 116.95, 121.56, 126.48, 129.45, 135.94, 136.73, 152.80, 158.59, 169.56 | DMSO-d6 | 1.82 (br s, 4H), 3.24 (t, 2H, J = 6.45 Hz), 4.39 (t, 2H, J = 5.75 Hz), 7.50 (t, 1H, J = 7.45 Hz), 7.65 (d, 1H, 7.45 Hz), 7.89 (t, 1H, J = 7.25 Hz), 8.09 (d, 1H, J = 7.75 Hz), 9.07 (br s, 4H) | null | 24.92, 27.35, 29.59, 69.96, 90.20, 116.95, 121.56, 126.48, 129.45, 135.94, 136.73, 152.80, 158.59, 169.56 | 0.446285 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 7-Amino-3-(2-bromoethoxy)-4-chloro-1H-isochromen-1-one (6a) Compound 4a (2.2 g, 6.3 mmol) was reduced on a Parr apparatus with hydrogen over 10% palladium on charcoal (50 mg) in ethanol (25 mL) until the reaction stopped absorbing hydrogen. The solution was filtered through celite and the filtrate was evaporated. The r... | 7-Amino-3-(2-bromoethoxy)-4-chloro-1H-isochromen-1-one | O=C1C2=C(C=CC(N)=C2)C(Cl)=C(OCCBr)O1 | 1H NMR: δ 3.63 (t, 2H, J = 6.46 Hz) 3.95 (br s, 2H) 4.56 (t, 2H, J = 6.36 Hz) 7.10 (dd, 1H, J = 2.58 Hz, 8.54 Hz) 7.43 (d, 1H, J = 2.58 Hz) 7.54 (d, 1H, J = 8.74 Hz) | 13C NMR: δ 28.18, 69.87, 93.59, 113.09, 119.21, 123.54, 124.04, 128.24, 145.63, 149.90, 159.47 | null | 3.63 (t, 2H, J = 6.46 Hz), 3.95 (br s, 2H), 4.56 (t, 2H, J = 6.36 Hz), 7.10 (dd, 1H, J = 2.58 Hz, 8.54 Hz), 7.43 (d, 1H, J = 2.58 Hz), 7.54 (d, 1H, J = 8.74 Hz) | null | 28.18, 69.87, 93.59, 113.09, 119.21, 123.54, 124.04, 128.24, 145.63, 149.90, 159.47 | 0.637429 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 7-Amino-3-(3-bromopropoxy)-4-chloro-1H-isochromen-1-one (6b) (75% yield) Yellow crystals: mp 106–107°C (lit. [24,26] 98–100°C); 1H NMR (DMSO-d6) δ 2.29 (m, 2H) 3.60 (t, 2H, J = 6.36 Hz) 4.42 (t, 2H, J = 5.76 Hz) 7.09 (dd, 1H, J = 2.09 Hz, 8.44 Hz) 7.42 (d, 1H, J = 1.99 Hz) 7.51 (d, 1H, J = 8.54 Hz); 13C NMR: δ 29.11, 3... | 7-Amino-3-(3-bromopropoxy)-4-chloro-1H-isochromen-1-one | O=C1C2=C(C=CC(N)=C2)C(Cl)=C(OCCCBr)O1 | 1H NMR (DMSO-d6) δ 2.29 (m, 2H) 3.60 (t, 2H, J = 6.36 Hz) 4.42 (t, 2H, J = 5.76 Hz) 7.09 (dd, 1H, J = 2.09 Hz, 8.44 Hz) 7.42 (d, 1H, J = 1.99 Hz) 7.51 (d, 1H, J = 8.54 Hz) | 13C NMR: δ 29.11, 32.36, 68.71, 93.35, 113.11, 119.17, 123.58, 123.91, 128.42, 145.56, 150.49, 159.74 | DMSO-d6 | 2.29 (m, 2H), 3.60 (t, 2H, J = 6.36 Hz), 4.42 (t, 2H, J = 5.76 Hz), 7.09 (dd, 1H, J = 2.09 Hz, 8.44 Hz), 7.42 (d, 1H, J = 1.99 Hz), 7.51 (d, 1H, J = 8.54 Hz) | null | 29.11, 32.36, 68.71, 93.35, 113.11, 119.17, 123.58, 123.91, 128.42, 145.56, 150.49, 159.74 | 0.577329 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [2-(7-amino-4-chloro-1-oxo-1H-isochromen-3-yloxy)ethyl]isothiourea hydrobromide (7a) (40% yield) Pale yellow solid: mp d 150°C; 1H NMR: (DMSO-d6) δ 3.59 (br s, 2H) 4.47 (br s, 2H) 5.81 (br s, 2H) 7.21 (d, 1H, J = 8.94 Hz) 7.26 (s, 1H) 7.44 (br d, 1H) 9.11 (br s, 4H);13C NMR: δ 29.73, 68.11, 90.48, 117.18, 121.72, 12... | 2- [2-(7-amino-4-chloro-1-oxo-1H-isochromen-3-yloxy)ethyl]isothiourea hydrobromide | N=C(N)SCCOC(OC1=O)=C(Cl)C2=C1C=C(N)C=C2.[H]Br | 1H NMR: (DMSO-d6) δ 3.59 (br s, 2H) 4.47 (br s, 2H) 5.81 (br s, 2H) 7.21 (d, 1H, J = 8.94 Hz) 7.26 (s, 1H) 7.44 (br d, 1H) 9.11 (br s, 4H) | 13C NMR: δ 29.73, 68.11, 90.48, 117.18, 121.72, 126.70, 129.48, 135.99, 136.56, 152.18, 158.35, 169.11 | DMSO-d6 | 3.59 (br s, 2H), 4.47 (br s, 2H), 5.81 (br s, 2H), 7.21 (d, 1H, J = 8.94 Hz), 7.26 (s, 1H), 7.44 (br d, 1H), 9.11 (br s, 4H) | null | 29.73, 68.11, 90.48, 117.18, 121.72, 126.70, 129.48, 135.99, 136.56, 152.18, 158.35, 169.11 | 0.627578 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [3-(7-Amino-4-chloro-1-oxo-1H-isochromen-3-yloxy)propyl]isothiourea hydrobromide (7b) A solution of 6b (0.25 g, 0.75 mmol), thiourea (0.071 g, 0.94 mmol) and tetrahydrofuran (25 mL) was refluxed for forty-eight hours to give a yellow precipitate. The precipitate was filtered and washed with hot tetrahydrofuran (3 × ... | 2- [3-(7-Amino-4-chloro-1-oxo-1H-isochromen-3-yloxy)propyl]isothiourea hydrobromide | N=C(N)SCCCOC(OC1=O)=C(Cl)C2=C1C=C(N)C=C2.[H]Br | 1H NMR: (DMSO-d6) δ 2.07 (br s, 2H) 3.30 (br s, 2H) 4.32 (br s, 2H) 7.16 (d, 1H, J = 7.94 Hz) 7.26 (s, 1H) 7.41 (d, 1H, J = 7.95 Hz) 9.05 (br s, 4H) | 13C NMR: δ 26.73, 28.35, 69.26, 92.87, 110.88, 118.81, 122.84, 123.11, 124.66, 148.23, 149.41, 159.06, 169.37 | DMSO-d6 | 2.07 (br s, 2H), 3.30 (br s, 2H), 4.32 (br s, 2H), 7.16 (d, 1H, J = 7.94 Hz), 7.26 (s, 1H), 7.41 (d, 1H, J = 7.95 Hz), 9.05 (br s, 4H) | null | 26.73, 28.35, 69.26, 92.87, 110.88, 118.81, 122.84, 123.11, 124.66, 148.23, 149.41, 159.06, 169.37 | 0.628242 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | N- [3-(2-Bromoethoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]benzamide (8a) To a solution of 6a (0.75 g, 2.4 mmol) in dry tetrahydrofuran (20 mL) was added benzoyl chloride (0.35 mL, 2.8 mmol) and triethylamine (0.33 mL, 2.3 mmol). The solution was stirred at room temperature for fourteen hours after which time the triethyl... | N- [3-(2-Bromoethoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]benzamide | O=C(NC1=CC2=C(C=C1)C(Cl)=C(OCCBr)OC2=O)C3=CC=CC=C3 | 1H NMR: (DMSO-d6) δ 3.83 (t, 2H, J = 5.46 Hz) 4.65 (t, 2H, J = 5.46 Hz) 7.56 (m, 3H) 7.71 (d, 1H, J = 8.93 Hz) 7.99 (d, 2H, J = 8.15) 8.29 (dd, 1H, J = 2.39 Hz, 8.74 Hz) 8.68 (d, 1H, J = 2.18 Hz) 10.63 (s, 1H) | 13C NMR: δ 30.49, 69.98, 91.08, 117.64, 119.23, 122.38, 127.52, 127.86, 128.20, 131.62, 131.90, 134.12, 137.90, 151.40, 158.35, 165.43 | DMSO-d6 | 3.83 (t, 2H, J = 5.46 Hz), 4.65 (t, 2H, J = 5.46 Hz), 7.56 (m, 3H), 7.71 (d, 1H, J = 8.93 Hz), 7.99 (d, 2H, J = 8.15), 8.29 (dd, 1H, J = 2.39 Hz, 8.74 Hz), 8.68 (d, 1H, J = 2.18 Hz), 10.63 (s, 1H) | null | 30.49, 69.98, 91.08, 117.64, 119.23, 122.38, 127.52, 127.86, 128.20, 131.62, 131.90, 134.12, 137.90, 151.40, 158.35, 165.43 | 0.612545 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | N- [3-(3-Bromopropoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]benzamide (8b) (82% yield) Pale yellow solid: mp 193–194°C; 1H NMR: (DMSO-d6) δ 2.28 (m, 2H) 3.66 (t, 2H, J = 6.56 Hz) 4.44 (t, 2H, J = 5.96 Hz) 7.55 (m, 3H) 7.68 (d, 1H, J = 8.74 Hz) 7.98 (d, 6.56 Hz) 8.25 (dd, 1H, J = 1.99 Hz, 8.74 Hz) 8.66 (d, 1H, J = 1.98 Hz)... | N- [3-(3-Bromopropoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]benzamide | O=C(NC1=CC2=C(C=C1)C(Cl)=C(OCCCBr)OC2=O)C3=CC=CC=C3 | 1H NMR: (DMSO-d6) δ 2.28 (m, 2H) 3.66 (t, 2H, J = 6.56 Hz) 4.44 (t, 2H, J = 5.96 Hz) 7.55 (m, 3H) 7.68 (d, 1H, J = 8.74 Hz) 7.98 (d, 6.56 Hz) 8.25 (dd, 1H, J = 1.99 Hz, 8.74 Hz) 8.66 (d, 1H, J = 1.98 Hz) 10.62 (s, 1H) | 13C NMR: δ 30.74, 32.09, 69.13, 91.36, 118.01, 119.74, 122.80, 127.88, 128.43, 128.67, 133.10, 132.46, 134.47, 138.15, 152.20, 158.95, 165.96 | DMSO-d6 | 2.28 (m, 2H), 3.66 (t, 2H, J = 6.56 Hz), 4.44 (t, 2H, J = 5.96 Hz), 7.55 (m, 3H), 7.68 (d, 1H, J = 8.74 Hz), 7.98 (d, 6.56 Hz), 8.25 (dd, 1H, J = 1.99 Hz, 8.74 Hz), 8.66 (d, 1H, J = 1.98 Hz), 10.62 (s, 1H) | null | 30.74, 32.09, 69.13, 91.36, 118.01, 119.74, 122.80, 127.88, 128.43, 128.67, 133.10, 132.46, 134.47, 138.15, 152.20, 158.95, 165.96 | 0.558359 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [2-(7-Benzamido-4-chloro-1-oxo-1H-isochromen-3-yloxy)ethyl]isothiourea hydrobromide (9a) A solution of 8a (0.3 g, 0.71 mmol) and thiourea (0.06 g, 0.78 mmol) in dry tetrahydrofuran (25 mL) was refluxed for twelve hours. The resulting pale yellow solids were filtered and washed with hot tetrahydrofuran (3 × 10 mL) to... | 2- [2-(7-Benzamido-4-chloro-1-oxo-1H-isochromen-3-yloxy)ethyl]isothiourea hydrobromide | N=C(N)SCCOC(OC1=O)=C(Cl)C2=C1C=C(NC(C3=CC=CC=C3)=O)C=C2.[H]Br | 1H NMR: (DMSO-d6) δ 3.68 (br s, 2H) 4.60 (br s, 2H) 7.59 (m, 3H) 7.74 (d, 1H, J = 8.54 Hz) 8.03 (d, 2H, J = 6.75 Hz) 8.32 (d, 1H, J = 8.14 Hz) 8.73 (s, 1H) 9.18 (br s, 4H) 10.69 (s, 1H) | 13C NMR: δ 29.85, 68.32, 91.00, 117.72, 119.47, 122.53, 127.60, 128.22, 128.33, 131.79, 132.06, 134.12, 137.96, 151.44, 158.43, 165.63, 169.18 | DMSO-d6 | 3.68 (br s, 2H), 4.60 (br s, 2H), 7.59 (m, 3H), 7.74 (d, 1H, J = 8.54 Hz), 8.03 (d, 2H, J = 6.75 Hz), 8.32 (d, 1H, J = 8.14 Hz), 8.73 (s, 1H), 9.18 (br s, 4H), 10.69 (s, 1H) | null | 29.85, 68.32, 91.00, 117.72, 119.47, 122.53, 127.60, 128.22, 128.33, 131.79, 132.06, 134.12, 137.96, 151.44, 158.43, 165.63, 169.18 | 0.596585 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 2- [3-(7-Benzamido-4-chloro-1-oxo-1H-isochromen-3-yloxy]propyl)isothiourea hydrobromide (9b) (25% yield) Pale yellow solid: mp 203–204°C;1H NMR: (DMSO-d6) δ 2.12 (m, 2H) 3.31 (br s, 2H) 4.44 (t, 2H, J = 5.66 Hz) 7.56 (m, 3H) 7.71 (d, 1H, J = 8.74 Hz) 8.00 (d, 2H, J = 6.95 Hz) 8.28 (d, 1H, J = 8.54 Hz) 8.70 (s, 1H) 9.07... | 2- [3-(7-Benzamido-4-chloro-1-oxo-1H-isochromen-3-yloxy]propyl)isothiourea hydrobromide | null | 1H NMR: (DMSO-d6) δ 2.12 (m, 2H) 3.31 (br s, 2H) 4.44 (t, 2H, J = 5.66 Hz) 7.56 (m, 3H) 7.71 (d, 1H, J = 8.74 Hz) 8.00 (d, 2H, J = 6.95 Hz) 8.28 (d, 1H, J = 8.54 Hz) 8.70 (s, 1H) 9.07 (br s, 4H) 10.65 (s, 1H) | 13C NMR: δ 27.21, 28.79, 69.37, 91.38, 118.13, 119.85, 122.92, 128.04, 128.60, 128.77, 132.21, 132.57, 134.61, 138.33, 152.36, 159.05, 166.02, 169.83 | DMSO-d6 | 2.12 (m, 2H), 3.31 (br s, 2H), 4.44 (t, 2H, J = 5.66 Hz), 7.56 (m, 3H), 7.71 (d, 1H, J = 8.74 Hz), 8.00 (d, 2H, J = 6.95 Hz), 8.28 (d, 1H, J = 8.54 Hz), 8.70 (s, 1H), 9.07 (br s, 4H), 10.65 (s, 1H) | null | 27.21, 28.79, 69.37, 91.38, 118.13, 119.85, 122.92, 128.04, 128.60, 128.77, 132.21, 132.57, 134.61, 138.33, 152.36, 159.05, 166.02, 169.83 | 0.514382 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(2-Bromoethoxy)-7-nitro-1H-isochromen-1-one (10a) A solution of 3a (1.5 g, 4.5 mmol) and trifluoroacetic anhydride (0.64 mL, 5.0 mmol) in dichloromethane (50 mL) was stirred at room temperature for sixteen hours. The solution was evaporated, washed with water (1 × 25 mL), saturated sodium bicarbonate solution (1 × 25... | 3-(2-Bromoethoxy)-7-nitro-1H-isochromen-1-one | O=C1C2=C(C=CC([N+]([O-])=O)=C2)C=C(OCCBr)O1 | 1H NMR: δ 3.65 (t, 2H, J = 5.96 Hz) 4.54 (t, 2H, J = 5.86 Hz) 5.77 (s, 1H) 7.42 (d, 1H, J = 8.74 Hz) 8.38 (d, 1H, J = 8.54 Hz) 8.96 (s, 1H) | 13C NMR: δ 27.51, 68.87, 81.12, 117.12, 125.70, 126.17, 129.28, 144.97, 145.11, 158.81, 160.02 | null | 3.65 (t, 2H, J = 5.96 Hz), 4.54 (t, 2H, J = 5.86 Hz), 5.77 (s, 1H), 7.42 (d, 1H, J = 8.74 Hz), 8.38 (d, 1H, J = 8.54 Hz), 8.96 (s, 1H) | null | 27.51, 68.87, 81.12, 117.12, 125.70, 126.17, 129.28, 144.97, 145.11, 158.81, 160.02 | 0.677589 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(3-Bromopropoxy)-7-nitro-1H-isochromen-1-one (10b) (55% yield) Yellow crystals: mp 117–118°C; 1H NMR: δ 2.37 (m, 2H) 3.59 (t, 2H, J = 6.26 Hz) 4.38 (t, 2H, J = 5.86 Hz) 5.72 (s, 1H) 7.43 (d, 1H, J = 8.74 Hz) 8.41 (dd, 1H, J = 2.48 Hz, 8.84 Hz) 9.02 (d, 1H, J = 2.19 Hz);13C NMR: δ 28.80, 31.46, 67.29, 80.02, 117.02, 1... | 3-(3-Bromopropoxy)-7-nitro-1H-isochromen-1-one | O=C1C2=C(C=CC([N+]([O-])=O)=C2)C=C(OCCCBr)O1 | 1H NMR: δ 2.37 (m, 2H) 3.59 (t, 2H, J = 6.26 Hz) 4.38 (t, 2H, J = 5.86 Hz) 5.72 (s, 1H) 7.43 (d, 1H, J = 8.74 Hz) 8.41 (dd, 1H, J = 2.48 Hz, 8.84 Hz) 9.02 (d, 1H, J = 2.19 Hz) | 13C NMR: δ 28.80, 31.46, 67.29, 80.02, 117.02, 125.55, 126.07, 129.15, 144.79, 145.21, 158.94, 160.89 | null | 2.37 (m, 2H), 3.59 (t, 2H, J = 6.26 Hz), 4.38 (t, 2H, J = 5.86 Hz), 5.72 (s, 1H), 7.43 (d, 1H, J = 8.74 Hz), 8.41 (dd, 1H, J = 2.48 Hz, 8.84 Hz), 9.02 (d, 1H, J = 2.19 Hz) | null | 28.80, 31.46, 67.29, 80.02, 117.02, 125.55, 126.07, 129.15, 144.79, 145.21, 158.94, 160.89 | 0.616135 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 3-(3-Bromopropoxy)-4-trifluoroacetyl-1H-isochromen-1-one (10c) A solution of 3d (0.60 g, 2.0 mmol) and trifluoroacetic anhydride (0.38 mL, 2.7 mmol) in dichloromethane (25 mL) was stirred at room temperature for fourteen hours. The solution was evaporated and the oil was chromatographed (chloroform) to afford 0.45 g (5... | 3-(3-Bromopropoxy)-4-trifluoroacetyl-1H-isochromen-1-one | O=C1C2=C(C=CC=C2)C(C(C(F)(F)F)=O)=C(OCCCBr)O1 | 1H NMR: δ 2.38 (m, 2H) 3.54 (t, 2H, J = 6.26 Hz) 4.70 (t, 2H, J = 5.96 Hz) 7.42 (m, 1H) 7.74 (m, 1H) 8.10 (d, 1H, J = 8.34 Hz) 8.22 (d, 1H, J = 7.95 Hz) | 13C NMR: δ 28.24, 31.37, 68.94, 90.90, 115.81, 116.01, 123.40, 126.75, 130.26, 135.87, 136.27, 157.73, 162.08, 179.97 | null | 2.38 (m, 2H), 3.54 (t, 2H, J = 6.26 Hz), 4.70 (t, 2H, J = 5.96 Hz), 7.42 (m, 1H), 7.74 (m, 1H), 8.10 (d, 1H, J = 8.34 Hz), 8.22 (d, 1H, J = 7.95 Hz) | null | 28.24, 31.37, 68.94, 90.90, 115.81, 116.01, 123.40, 126.75, 130.26, 135.87, 136.27, 157.73, 162.08, 179.97 | 0.617115 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1479381 | 7-Amino-3-(2-bromoethoxy)-1H-isochromen-1-one (11) A solution of 10a (1.5 g, 4.7 mmol) in methanol/ethyl acetate (1:1, 25 mL) was reduced on a Parr apparatus with hydrogen and 10% palladium on charcoal. After the reaction stopped absorbing hydrogen it was filtered through celite and the celite was washed with methylene... | 7-Amino-3-(2-bromoethoxy)-1H-isochromen-1-one | O=C1C2=C(C=CC(N)=C2)C=C(OCCBr)O1 | 1H NMR: (DMSO-d6) 3.79 (t, 2H, J = 5.17 Hz) 4.36 (t, 2H, J = 4.97 Hz) 5.50 (s, 2H) 5.82 (s, 1H) 7.03 (d, 1H, J = 8.54 Hz) 7.19 (m, 2H) | 13C NMR: δ 30.30, 68.71, 80.35, 110.20, 117.91, 123.17, 125.84, 128.03, 147.16, 154.71, 160.45 | DMSO-d6 | 3.79 (t, 2H, J = 5.17 Hz), 4.36 (t, 2H, J = 4.97 Hz), 5.50 (s, 2H), 5.82 (s, 1H), 7.03 (d, 1H, J = 8.54 Hz), 7.19 (m, 2H) | null | 30.30, 68.71, 80.35, 110.20, 117.91, 123.17, 125.84, 128.03, 147.16, 154.71, 160.45 | 0.665117 | 16,466,576 | BMC Chem Biol. 2006 Feb 8; 6:1 | BMC Chem Biol | 2,006 | CC BY | 2021-01-04 16:30:50 | no |
PMC1686302 | are presented in Table 5. The ligand H2L1 showed seven signals in the 13C-NMR spectra resonating at δ 131.91, 128.08, 126.70, 125.58, 123.92, 123.76, and 115.95 ppm for thirteen | H2L1 | null | null | The ligand H2L1 showed seven signals in the 13C-NMR spectra resonating at δ 131.91, 128.08, 126.70, 125.58, 123.92, 123.76, and 115.95 ppm for thirteen | null | null | null | 131.91, 128.08, 126.70, 125.58, 123.92, 123.76, 115.95 | 0.487334 | 17,497,005 | Bioinorg Chem Appl. 2006 Mar 20; 2006:25651 | Bioinorg Chem Appl | 2,006 | CC BY | 2021-01-05 10:03:05 | no |
PMC1698928 | 3-Butyl-11-cyclopentyl-6,7,8,9-tetrahydrodiazepino [1,2,3-cd]purine-2,4-dione (18) To a solution of 8-butyl-10-cyclopentanecarboxamido-1,2,3,4,5,7,8,9-octahydropyrimido [1,6-c][1,3]diazepine-7,9-dione (16) [6] (0.17 g, 0.5 mmol) in THF (1 ml) in a 10 ml pressure vial, HMDS (1 ml) was added. Microwave irradiation was ap... | 3-Butyl-11-cyclopentyl-6,7,8,9-tetrahydrodiazepino [1,2,3-cd]purine-2,4-dione | null | 1H-NMR (500 MHz, CDCl3) δ = 0.90 (t, 3H, J = 7.4 Hz, CH3), 1.35 (sex, J = 7.4 Hz, 2H), 1.61 (m, 4H), 1.81 (m, 2H), 1.99 (m, 4H), 2.16 (quint, 4H, J = 2.8 Hz), 3.04 (quint, 1H, J = 8.1 Hz), 3.99 (dd, 2H, J = 7.3 Hz, J = 7.4 Hz), 4.16 (m, 2H), 4.31 (m, 2H) | 13C-NMR (500 MHz, CDCl3) δ = 13.83, 20.14, 25.23, 25.54, 25.61, 30.07, 31.37, 37.12, 41.57, 42.82, 43.46, 115.57, 141.03, 151.17, 151.66, 157.24 | 500 MHz, CDCl3 | 0.90 (t, 3H, J = 7.4 Hz, CH3), 1.35 (sex, J = 7.4 Hz, 2H), 1.61 (m, 4H), 1.81 (m, 2H), 1.99 (m, 4H), 2.16 (quint, 4H, J = 2.8 Hz), 3.04 (quint, 1H, J = 8.1 Hz), 3.99 (dd, 2H, J = 7.3 Hz, J = 7.4 Hz), 4.16 (m, 2H), 4.31 (m, 2H) | 500 MHz, CDCl3 | 13.83, 20.14, 25.23, 25.54, 25.61, 30.07, 31.37, 37.12, 41.57, 42.82, 43.46, 115.57, 141.03, 151.17, 151.66, 157.24 | 0.921238 | 17,067,400 | Beilstein J Org Chem. 2006 Oct 27; 2:20 | Beilstein J Org Chem | 2,006 | CC BY | 2021-02-20 23:14:52 | no |
PMC1803790 | 2. Results and discussions Cimicifoetiside A (1) (see Figure 1) exhibited a molecular formula of C37H58O10 based on its 13C-NMR DEPT spectrum and negative HRFABMS in which a fragment ion was observed at m/z 619.3854 [M-H-OAc]- (calcd for C35H55O9, 619.3846) due to the facile loss of an acetyl group. The overall physica... | Cimicifoetiside A | null | In the 1H-NMR spectrum (Table 1), the characteristic cyclopropane methylene signals at δH 0.22 and 0.46 (each 1H, d, J = 3.0 Hz); eight methyl groups at δH 0.93, 1.05, 1.12, 1.18, 1.44, 1.47 (each 3H, s), 0.85 (d, J = 5.1 Hz), and an acetyl group at δ 2.09 (3H, s); and an anomeric proton at δH 4.75 (1H, d, J = 7.8 Hz) ... | The 13C-NMR and DEPT spectra (Table 1), showed a total of 37 carbon signals, among which, 30 were ascribable to the triterpene aglycone. A characteristic ketalic quaternary carbon signal was observed at δC 112.0 (s, C-16) together with two oxygen-bearing methine signals at δC 80.3 (d, C-15) and 90.2 (d, C-24). Two carb... | null | 0.22, 0.46 (each 1H, d, J = 3.0 Hz), 0.93, 1.05, 1.12, 1.18, 1.44, 1.47 (each 3H, s), 0.85 (d, J = 5.1 Hz), 2.09 (3H, s), 4.75 (1H, d, J = 7.8 Hz) | null | 112.0, 80.3, 90.2, 170.2, 21.4, 104.5, 74.4, 72.5, 69.8, 67.3 | 0.159153 | 17,266,751 | Beilstein J Org Chem. 2007 Jan 31; 3:3 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:54 | no |
PMC1803790 | Figure 2 Key long-range 13C-1H correlations of 1 observed by HMBC. In the HMBC spectrum (See Figure 2), an informative correlation was also observed between the anomeric proton signal at δH 4.73 (H-1', 1H, J = 6.7 Hz) and a methine carbon signal at δC 88.7 (C-3), implying that the sugar moiety was linked at the C-3 pos... | cimicifoetiside A | null | In the HMBC spectrum (See Figure 2), an informative correlation was also observed between the anomeric proton signal at δH 4.73 (H-1', 1H, J = 6.7 Hz) and a methine carbon signal at δC 88.7 (C-3), implying that the sugar moiety was linked at the C-3 position. The typical large coupling constants between H-1' and H-2' (... | Furthermore, the location of the acetyl group could be unambiguously assigned to C-2' of the arabinose unit by HMBC, as a correlation was observed between H-2' (δH 5.90, t, J = 6.7 Hz) and the carbonyl signal at δ 170.2. On mild alkali hydrolysis with saturated Na2CO3-MeOH solution, 1 afforded a deacetyl derivative whi... | null | 4.73 (H-1', 1H, J = 6.7 Hz), 88.7 (C-3), 5.90, t, J = 6.7 Hz (H-2'), 170.2 (carbonyl signal) | null | 170.2 | 0.000048 | 17,266,751 | Beilstein J Org Chem. 2007 Jan 31; 3:3 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:54 | no |
PMC1803790 | Cimicifoetiside B (2) was determined to have a molecular formula of C39H60O11 based on its 13C-NMR (DEPT) spectral data and HRFABMS, in which a fragment ion was detected at m/z 661.3944 [M-H-OAc]- (calcd for C37H57O10, 661.3951) due to the loss of an acetyl group, indicating a 42 a.m.u. increase compared to that of 1, ... | 25-O-acetylcimigenol 3-O-α-L-(2'-O-acetyl) arabinopyranoside | null | The second acetyl group could be readily attributed to the hydroxyl group at C-25, as a significant downfield shift (12.1 ppm) of C-25, and up-field shifts of C-24 (3.2 ppm), C-26 (3.2 ppm), and C-27 (3.9 ppm) were observed in its 13C-NMR spectrum compared with those of 1, obeying the 'acylation effect' [13] with respe... | The second acetyl group could be readily attributed to the hydroxyl group at C-25, as a significant downfield shift (12.1 ppm) of C-25, and up-field shifts of C-24 (3.2 ppm), C-26 (3.2 ppm), and C-27 (3.9 ppm) were observed in its 13C-NMR spectrum compared with those of 1, obeying the 'acylation effect' [13] with respe... | null | 12.1, 3.2, 3.2, 3.9 | null | 12.1, 3.2, 3.2, 3.9 | 0.02004 | 17,266,751 | Beilstein J Org Chem. 2007 Jan 31; 3:3 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:54 | no |
PMC1810298 | Reaction of benzoxasilocines with aromatic aldehydes in the presence of BF3·Et2O We had previously observed [4] that the treatment of the seven membered cyclic allylsiloxane 2,3-dihydro-2,2-dimethylbenzo[f][1,2]oxasilepine with boron trifluoride yielded a ring-opened fluorinated derivative. This derivative was able to ... | 6 | null | 1H NMR is very similar to that of the starting material, but for the methyl groups on silicon, which appear now as doublets due to their coupling with the 19F (3JH-F = 7.3 Hz). This coupling is also observed for the methylene on silicon H4', which exhibits now an additional splitting (3JH-F = 6.5 Hz) | 13C NMR also reveals the presence of the fluorine on the silicon, because the signal due to the methyl groups appears as a doublet (2JC-F = 14.8 Hz) as well as the signal due to C4' (2JC-F = 13.5 Hz) | null | 7.3, 6.5 | null | 14.8, 13.5 | 0.08211 | 17,288,601 | Beilstein J Org Chem. 2007 Feb 8; 3:5 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:55 | no |
PMC1847824 | Results and Discussion The synthesis of 9-aryl-dimethyl-5,6,7,9-tetrahydro-1,2,4-triazolo-[5,1-b]quinazolin-8(4H)-ones by refluxing equimolar amounts of aromatic aldehydes (1, C6H5-, 4-OCH3-C6H4-, 4-NMe2-C6H4-, 4-Cl-C6H4- and 4-NO2C6H4-), 5-amino-1(H)-1,2,4-triazole (2) and dimedone (3) in DMF or methanol has been repo... | 9-aryl-dimethyl-5,6,7,9-tetrahydro-1,2,4-triazolo-[5,1-b]quinazolin-8(4H)-ones | O=C1C2=C(NC3=NC=NN3[C@H]2CCCCC)CC(C)C1C | The δ values of the most carbon signals could be determined and assigned to the corresponding carbon atoms | The 13C NMR spectrum of compound 4b revealed fourteen distinctive carbon signals at δC 192.0, 156.6, 150.1, 148.90, 133.8, 130.0, 128.8, 128.0, 127.6, 126.8, 113.0, 57.2, 98.8 and 49.8 corresponding to C-8, Ar-C-4a, CH-3, Ar-C-2', Ar-C-1', Ar-CH-6', Ar-CH-3', Ar-CH-4', C-5a, Ar-CH-5', C-8a, OCH3, CH-9, and C-7 respecti... | null | null | null | 192.0, 156.6, 150.1, 148.90, 133.8, 130.0, 128.8, 128.0, 127.6, 126.8, 113.0, 57.2, 98.8, 49.8 | 0.019771 | 17,338,816 | Beilstein J Org Chem. 2007 Mar 5; 3:11 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:57 | no |
PMC1847824 | via microwave irradiation. To test the reactivity of compounds 4a-c towards oxidation, we refluxed a mixture of 2,3,5,6-tetrachloro-1,4-benzoquinone (5) and 4a-c in cholorobenzene (Scheme 2). The reaction proceeded after long time of refluxing to give compounds 6a-c in good yields. The structure feature of the products... | 6a-c | null | The IR spectra did not show any absorption due to the presence of NH group and this was also noted in the 1H NMR spectra. The disappearance of 9-H in the 1H NMR spectra and the appearance of C-5a in the 13C NMR spectra as an azomethine carbon signal at δ = 154.8–155.2 indicated that only the NH and 9-H protons were rem... | The IR spectra did not show any absorption due to the presence of NH group and this was also noted in the 1H NMR spectra. The disappearance of 9-H in the 1H NMR spectra and the appearance of C-5a in the 13C NMR spectra as an azomethine carbon signal at δ = 154.8–155.2 indicated that only the NH and 9-H protons were rem... | null | 9-H | null | 154.8–155.2 | 0.044731 | 17,338,816 | Beilstein J Org Chem. 2007 Mar 5; 3:11 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:57 | no |
PMC1930152 | Supporting Information Figure S1 13C-NMR analysis of the CFE from Pseudomonas fluorescens grown in a defined medium containing Ga-citrate. 2 mg/ml protein equivalent of CFE was incubated for 1h in a phosphate reaction buffer containing 5 mM Ga-13C2-2,4-citrate, 5 mM malonate, and NAD. The reaction was stopped by boilin... | CFE | null | null | 13C-NMR analysis of the CFE from Pseudomonas fluorescens grown in a defined medium containing Ga-citrate | null | null | null | 5 mM Ga-13C2-2,4-citrate, 5 mM malonate, and NAD | 0.067071 | 17,668,068 | PLoS One. 2007 Aug 1; 2(8):e690 | PLoS One | 2,007 | CC BY | 2021-01-05 15:30:39 | no |
PMC1942119 | To a stirred solution of methyl (2-bromothiophen-3-yl)acetate (120 mg, 0.51 mmol) and 4-iodo-3-nitrobenzoyl chloride (150 mg, 0.48 mmol) in anhydrous CH2Cl2 (10 mL) was added AlCl3 (260 mg, 1.95 mmol) in four portions at 10-minute intervals at room temperature. The resulting mixture was stirred overnight. The reaction ... | 7 | null | 1H NMR (400 MHz, CDCl3) δ 8.27 (d, 1H, J = 2.0 Hz), 8.22 (d, 1H, J = 8.0 Hz), 7.70 (dd, 1H, J = 2.0, 8.2 Hz), 7.48 (s, 1H), 3.74 (s, 3H) and 3.68 (s, 2H) | 13C NMR (100 MHz, CDCl3) δ 183.8, 170.0, 153.2, 142.9, 141.9, 138.3, 136.5, 135.8, 133.1, 125.7, 124.5, 91.8, 52.6 and 35.0 | 400 MHz, CDCl3 | 8.27 (d, 1H, J = 2.0 Hz), 8.22 (d, 1H, J = 8.0 Hz), 7.70 (dd, 1H, J = 2.0, 8.2 Hz), 7.48 (s, 1H), 3.74 (s, 3H), 3.68 (s, 2H) | 100 MHz, CDCl3 | 183.8, 170.0, 153.2, 142.9, 141.9, 138.3, 136.5, 135.8, 133.1, 125.7, 124.5, 91.8, 52.6, 35.0 | 0.787554 | 17,712,409 | PLoS One. 2007 Aug 22; 2(8):e761 | PLoS One | 2,007 | CC0 | 2021-01-05 15:30:42 | no |
PMC1942119 | A solution of 7 (150 mg, 0.29 mmol), phenylacetylene (32 µL, 0.29 mmol), Pd(PPh3)2Cl2 (21 mg, 0.03 mmol), K2CO3 (42 mg, 0.29 mmol), and Et3N (40 µL, 0.29 mmol) in DMF (3 mL) was stirred for 24 hours at room temperature. Water (5 mL) was added to the mixture and then extracted with EtOAc (3×10 mL). The combined organic ... | 8 | null | 1H NMR (400 MHz, CDCl3) δ 8.54 (d, 1H, J = 1.6 Hz,); 8.06 (dd, 1H, J = 1.6, 8.0 Hz), 7.86 (d, 1H, J = 8.4 Hz), 7.64 (m, 2H), 7.52 (s, 1H), 7.42 (m, 3H), 3.75 (s, 3H) and 3.70 (s, 2H) | 13C NMR (100 MHz, CDCl3) δ 183.9, 170.1, 149.5, 142.2, 137.0, 136.3, 135.7, 135.3, 132.9, 132.5, 130.1, 128.8, 125.6, 124.3, 122.8, 122.1, 101.1, 84.7, 52.7 and 35.0 | 400 MHz, CDCl3 | 8.54 (d, 1H, J = 1.6 Hz,), 8.06 (dd, 1H, J = 1.6, 8.0 Hz), 7.86 (d, 1H, J = 8.4 Hz), 7.64 (m, 2H), 7.52 (s, 1H), 7.42 (m, 3H), 3.75 (s, 3H), 3.70 (s, 2H) | 100 MHz, CDCl3 | 183.9, 170.1, 149.5, 142.2, 137.0, 136.3, 135.7, 135.3, 132.9, 132.5, 130.1, 128.8, 125.6, 124.3, 122.8, 122.1, 101.1, 84.7, 52.7, 35.0 | 0.613109 | 17,712,409 | PLoS One. 2007 Aug 22; 2(8):e761 | PLoS One | 2,007 | CC0 | 2021-01-05 15:30:42 | no |
PMC1942119 | To a solution of 8 (25 mg, 0.05 mmol) in EtOAc (5 mL) was added stannous chloride dihydrate (58 mg, 0.26 mmol). The resulting mixture was refluxed for one hour under N2. The reaction mixture was poured onto ice (5 g), and basified with saturated NaHCO3 solution to pH 8. The white milky mixture was filtered through a Ce... | methyl (2-bromo-5-(3-amino-4-(phenylethynyl)benzoyl)thiophen-3-yl)acetate | O=C(OC)CC1=C(Br)SC(C(C2=CC=C(C#CC3=CC=CC=C3)C(N)=C2)=O)=C1 | 1H NMR (400 MHz, CDCl3) δ 7.55 (m, 2H), 7.50 (s, 1H), 7.48 (d, 1H, J = 1.6 Hz), 7.38 (m, 3H), 7.17 (m, 2H), 4.40 (br, 2H), 3.73 (s, 3H) and 3.66 (s, 2H) | 13C NMR (100 MHz, CDCl3) δ 186.7, 170.3, 148.1, 143.4, 138.1, 135.9, 135.1, 132.4, 131.8, 129.0, 128.7, 122.9, 122.8, 118.8, 114.5, 112.3, 97.6, 85.3, 52.6 and 35.0 | 400 MHz, CDCl3 | 7.55 (m, 2H), 7.50 (s, 1H), 7.48 (d, 1H, J = 1.6 Hz), 7.38 (m, 3H), 7.17 (m, 2H), 4.40 (br, 2H), 3.73 (s, 3H), 3.66 (s, 2H) | 100 MHz, CDCl3 | 186.7, 170.3, 148.1, 143.4, 138.1, 135.9, 135.1, 132.4, 131.8, 129.0, 128.7, 122.9, 122.8, 118.8, 114.5, 112.3, 97.6, 85.3, 52.6, 35.0 | 0.773683 | 17,712,409 | PLoS One. 2007 Aug 22; 2(8):e761 | PLoS One | 2,007 | CC0 | 2021-01-05 15:30:42 | no |
PMC1942119 | To a 250 mL flask containing freshly distilled toluene (50 mL) were added methyl (2-bromo-5-(3-amino-4-(phenylethynyl)benzoyl)thiophen-3-yl)acetate (2.93 g, 6.45 mmol) and indium tribromide (1.14 g, 3.22 mmol) under N2. The resulting mixture was refluxed for one hour. The solvent was removed in vacuo. MPLC purification... | 9 | null | 1H NMR (400 MHz, CDCl3) δ 9.38 (br, 1H), 7.98 (s, 1H), 7.69 (d, 2H, J = 7.8 Hz), 7.58 (m, 2H), 7.47 (s, 1H), 7.40 (t, 2H, J = 7.5 Hz), 7.30 (m, 1 H), 6.80 (s, 1H), 3.65 (s, 3H) and 3.59 (s, 2H) | 13C NMR (100 MHz, CDCl3) δ 187.4, 170.5, 144.2, 142.3, 136.5, 135.7, 134.9, 133.3, 131.8, 130.9, 129.4, 128.8, 125.9, 121.9, 120.4, 113.5, 100.3, 52.6 and 35.2 | 400 MHz, CDCl3 | 9.38 (br, 1H), 7.98 (s, 1H), 7.69 (d, 2H, J = 7.8 Hz), 7.58 (m, 2H), 7.47 (s, 1H), 7.40 (t, 2H, J = 7.5 Hz), 7.30 (m, 1 H), 6.80 (s, 1H), 3.65 (s, 3H), 3.59 (s, 2H) | 100 MHz, CDCl3 | 187.4, 170.5, 144.2, 142.3, 136.5, 135.7, 134.9, 133.3, 131.8, 130.9, 129.4, 128.8, 125.9, 121.9, 120.4, 113.5, 100.3, 52.6, 35.2 | 0.538649 | 17,712,409 | PLoS One. 2007 Aug 22; 2(8):e761 | PLoS One | 2,007 | CC0 | 2021-01-05 15:30:42 | no |
PMC1942119 | To a stirred solution of 9 (45 mg, 0.10 mmol) in anhydrous CH3CN (5 mL) was added CsF-Celite (125 mg) under N2, followed by adding N-(4-bromobutyl)-phthalimide (28 mg, 0.10 mmol). The resulting mixture was refluxed for five hours, cooled to room temperature, and filtered. The filtrate was evaporated in vacuo. MPLC puri... | 10 | null | 1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.74 (m, 6H), 7.59 (s, 1H), 7.47 (m, 5H), 6.60 (s, 1H), 4.32 (t, 2H, J = 7.2 Hz), 3.73 (s, 3H), 3.71 (s, 2H), 3.52 (t, 2H, J = 6.8 Hz), 1.72 (m, 2H) and 1.51 (m, 2H) | 13C NMR (100 MHz, CDCl3) δ 187.3, 170.4, 168.5, 145.2, 144.3, 136.8, 135.6, 134.9, 134.2, 134.1, 132.5, 132.1, 130.7, 129.5, 129.0, 128.8, 123.5, 123.4, 121.5, 120.6, 112.5, 103.1, 52.5, 43.7, 37.3, 35.1, 27.4 and 25.8 | 400 MHz, CDCl3 | 7.98 (s, 1H), 7.74 (m, 6H), 7.59 (s, 1H), 7.47 (m, 5H), 6.60 (s, 1H), 4.32 (t, 2H, J = 7.2 Hz), 3.73 (s, 3H), 3.71 (s, 2H), 3.52 (t, 2H, J = 6.8 Hz), 1.72 (m, 2H), 1.51 (m, 2H) | 100 MHz, CDCl3 | 187.3, 170.4, 168.5, 145.2, 144.3, 136.8, 135.6, 134.9, 134.2, 134.1, 132.5, 132.1, 130.7, 129.5, 129.0, 128.8, 123.5, 123.4, 121.5, 120.6, 112.5, 103.1, 52.5, 43.7, 37.3, 35.1, 27.4, 25.8 | 0.807789 | 17,712,409 | PLoS One. 2007 Aug 22; 2(8):e761 | PLoS One | 2,007 | CC0 | 2021-01-05 15:30:42 | no |
PMC1942119 | To a solution of 3-hydroxyphenylboronic acid (32 mg, 0.23 mmol) in EtOH (1 mL, degassed with N2), was added a solution of 10 (153 mg, 0.23 mmol) in toluene (5 mL), followed by adding Pd(PPh3)2Cl2 (16.3 mg, 0.023 mmol) and Na2CO3 (50 mg, 0.46 mmol). The reaction mixture was refluxed for three hours under N2, and then th... | 11 | null | 1H NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.70 (m, 2H), 7.64–7.59 (m, 4H), 7.42–7.33 (m, 6H), 7.24 (t, 1H, J = 7.9 Hz), 7.07 (t, 1H, J = 2.0 Hz), 6.97 (d, 1H, J = 7.6 Hz), 6.85 (dd, 1H, J = 2.0, 7.9 Hz), 6.52 (s, 1H), 4.23 (t, 2H, J = 7.0 Hz), 3.67 (s, 3H), 3.62 (s, 2H), 3.45 (t, 2H, J = 6.8 Hz), 1.67 (m, 2H) and 1.42 (m... | 13C NMR (100 MHz, CDCl3) δ 188.6, 171.9, 168.8, 157.0, 149.2, 145.2, 141.6, 137.8, 136.7, 134.3, 132.6, 132.1, 131.3, 130.5, 130.4, 129.5, 129.0, 128.8, 123.5, 121.7, 121.3, 120.7, 116.5, 112.8, 103.2, 52.6, 43.7, 37.5, 34.6, 27.5 and 25.9 | 400 MHz, CDCl3 | 7.98 (s, 1H), 7.70 (m, 2H), 7.64–7.59 (m, 4H), 7.42–7.33 (m, 6H), 7.24 (t, 1H, J = 7.9 Hz), 7.07 (t, 1H, J = 2.0 Hz), 6.97 (d, 1H, J = 7.6 Hz), 6.85 (dd, 1H, J = 2.0, 7.9 Hz), 6.52 (s, 1H), 4.23 (t, 2H, J = 7.0 Hz), 3.67 (s, 3H), 3.62 (s, 2H), 3.45 (t, 2H, J = 6.8 Hz), 1.67 (m, 2H), 1.42 (m, 2H) | 100 MHz, CDCl3 | 188.6, 171.9, 168.8, 157.0, 149.2, 145.2, 141.6, 137.8, 136.7, 134.3, 132.6, 132.1, 131.3, 130.5, 130.4, 129.5, 129.0, 128.8, 123.5, 121.7, 121.3, 120.7, 116.5, 112.8, 103.2, 52.6, 43.7, 37.5, 34.6, 27.5, 25.9 | 0.809587 | 17,712,409 | PLoS One. 2007 Aug 22; 2(8):e761 | PLoS One | 2,007 | CC0 | 2021-01-05 15:30:42 | no |
PMC1991597 | Chemoenzymatic synthesis of coniferyl acetate ((E)-4-hydroxy-3-methoxycinnamylacetate) Coniferyl alcohol (180.2 mg, 1.0 mmol), Candida antarctica lipase B (CAL-B, 25 mg, Aldrich, ≥10,000 U/g), vinyl acetate (401 µL, 5.0 mmol), and dry diethyl ether (Et2O, 50 mL, 0.2 M) were stirred in a 125-mL Erlenmeyer flask at room ... | (E)-4-hydroxy-3-methoxycinnamylacetate | O=C([O-])CC/C=C/C1=CC=C(O)C(OC)=C1 | 1H NMR (500 MHz, CDCl3) δ 6.91 (m, 3H), 6.59 (d, J = 15.92 Hz, 1H), 6.15 (dt, J = 6.62, 15.92 Hz, 1H), 4.72 (d, J = 6.62 Hz, 2H), 3.92 (s, 3H), 2.11 (s, 3H) | 13C NMR (125 MHz, CDCl3) δ 171.2, 146.8, 146.1, 134.7, 129.0, 121.0, 120.9, 114.7, 108.6, 65.5, 56.1, 21.3 | 500 MHz, CDCl3 | 6.91 (m, 3H), 6.59 (d, J = 15.92 Hz, 1H), 6.15 (dt, J = 6.62, 15.92 Hz, 1H), 4.72 (d, J = 6.62 Hz, 2H), 3.92 (s, 3H), 2.11 (s, 3H) | 125 MHz, CDCl3 | 171.2, 146.8, 146.1, 134.7, 129.0, 121.0, 120.9, 114.7, 108.6, 65.5, 56.1, 21.3 | 0.54054 | 17,912,370 | PLoS One. 2007 Oct 3; 2(10):e993 | PLoS One | 2,007 | CC BY | 2021-01-05 15:29:41 | no |
PMC1991597 | 4-((2-methoxyethoxy)methoxy)-3-methoxy benzaldehyde (step 1). K2CO3 (1.38 g, 10.0 mmol, 1.0 eq.) was added to solution of vanillin (1.52 g, 10.0 mmol, 1.0 eq.) in dry acetone (70 mL, 0.15 M), and the mixture was stirred under argon at 0°C for 30 min. Then MeOCH2CH2OCH2Cl (MEM-Cl, 1.49 g, 12.0 mmol, 1.2 eq.) was added d... | 4-((2-methoxyethoxy)methoxy)-3-methoxy benzaldehyde | O=CC1=CC=C(OCOCCOC)C(OC)=C1 | 1H NMR (500 MHz, CDCl3) δ 9.86 (s, 1H), 7.43 (s, 1H), 7.42 (d, J = 8.5 Hz, 2H), 7.32 (d, J = 8.5 Hz, 2H), 5.41 (s, 2H), 3.93 (s, 3H), 3.86 (t, J = 4.7 Hz, 2H), 3.54 (t, J = 4.7 Hz, 2H), 3.35 (s, 3H) | 13C NMR (125 MHz, CDCl3) δ 191.0, 152.0, 150.0, 131.1, 126.5, 114.8, 109.4, 94.0, 71.4, 68.2, 59.0, 56.0 | 500 MHz, CDCl3 | 9.86 (s, 1H), 7.43 (s, 1H), 7.42 (d, J = 8.5 Hz, 2H), 7.32 (d, J = 8.5 Hz, 2H), 5.41 (s, 2H), 3.93 (s, 3H), 3.86 (t, J = 4.7 Hz, 2H), 3.54 (t, J = 4.7 Hz, 2H), 3.35 (s, 3H) | 125 MHz, CDCl3 | 191.0, 152.0, 150.0, 131.1, 126.5, 114.8, 109.4, 94.0, 71.4, 68.2, 59.0, 56.0 | 0.95673 | 17,912,370 | PLoS One. 2007 Oct 3; 2(10):e993 | PLoS One | 2,007 | CC BY | 2021-01-05 15:29:41 | no |
PMC1991597 | 1-((2-methoxyethoxy)methoxy)-2-methoxy-4-vinylbenzene (step 2). To a suspension of methyltriphenylphosphonium bromide (MeP(Ph)3Br, 3.57 g, 10.0 mmol, 2.0 eq.) in anhydrous tetrahydrofuran (THF, 30 mL, 0.33 M), under argon at room temperature, was added potassium bis-trimethylsilylamide (KN(TMS)2, 4.5 mL, 9.0 mmol, 1.8 ... | 1-((2-methoxyethoxy)methoxy)-2-methoxy-4-vinylbenzene | C=CC1=CC=C(OCOCCOC)C(OC)=C1 | 1H NMR (500 MHz, CDCl3) δ 7.15 (d, J = 8.3 Hz, 1H), 6.96 (s, 1H), 6.93 (d, J = 8.3 Hz, 1H), 6.65 (dd, J = 10.9, 17.5 Hz, 1H), 5.63 (d, J = 17.4 Hz, 1H), 5.32 (s, 2H), 5.17 (d, J = 10.9 Hz, 1H), 3.90 (s, 3H), 3.87 (t, J = 4.7 Hz, 2H), 3.56 (t, J = 4.7 Hz, 2H), 3.37 (s, 3H) | 13C NMR (125 MHz, CDCl3) δ 149.7, 146.4, 136.4, 132.3, 119.4, 116.2, 112.4, 109.1, 94.4, 71.5, 67.8, 59.0, 55.8 | 500 MHz, CDCl3 | 7.15 (d, J = 8.3 Hz, 1H), 6.96 (s, 1H), 6.93 (d, J = 8.3 Hz, 1H), 6.65 (dd, J = 10.9, 17.5 Hz, 1H), 5.63 (d, J = 17.4 Hz, 1H), 5.32 (s, 2H), 5.17 (d, J = 10.9 Hz, 1H), 3.90 (s, 3H), 3.87 (t, J = 4.7 Hz, 2H), 3.56 (t, J = 4.7 Hz, 2H), 3.37 (s, 3H) | 125 MHz, CDCl3 | 149.7, 146.4, 136.4, 132.3, 119.4, 116.2, 112.4, 109.1, 94.4, 71.5, 67.8, 59.0, 55.8 | 0.906277 | 17,912,370 | PLoS One. 2007 Oct 3; 2(10):e993 | PLoS One | 2,007 | CC BY | 2021-01-05 15:29:41 | no |
PMC1991597 | (1S,2S)-ethyl 2-(4-hydroxy-3-methoxyphenyl) cyclo-propanecarboxylate (step 3). To a solution of copper-ligand complex prepared from CuIOTf (toluene)0.5 (129.3 mg, 0.25 mmol, 2.0 mol%) and ligand (A) (75.3 mg, 0.25 mmol, 2.0 mol%) in 50 mL of dry dichloromethane (DCM) was added 1-((2-methoxyethoxy)methoxy)-2-methoxy-4-v... | (1S,2S)-ethyl 2-(4-hydroxy-3-methoxyphenyl) cyclo-propanecarboxylate | O=C([C@@H]1[C@@H](C2=CC=C(O)C(OC)=C2)C1)OCC | 1H NMR (500 MHz, CDCl3) δ 6.82 (d, J = 8.2 Hz, 1H), 6.64 (s, 1H), 6.59 (d, J = 8.2 Hz, 1H), 5.56, ( br s, Ar-OH, 1H), 4.17 (q, J = 7.0 Hz, 2H), 3.87 (s, 3H), 2.47 (ddd, J = 4.6, 6.4, 9.6 Hz, 1H), 1.82 (ddd, J = 4.6, 5.6, 8.8 Hz, 1H), 1.54 (ddd, J = 4.8, 5.6, 9.2 Hz, 1H), 1.28 (t, J = 7.1 Hz, 3H)1.25 (ddd, buried, 1H) | 13C NMR (125 MHz, CDCl3) δ 173.6, 146.5, 144.3, 131.9, 118.8, 114.3, 109.4, 60.7, 55.9, 26.1, 23.8, 16.7, 14.3 | 500 MHz, CDCl3 | 6.82 (d, J = 8.2 Hz, 1H), 6.64 (s, 1H), 6.59 (d, J = 8.2 Hz, 1H), 5.56, ( br s, Ar-OH, 1H), 4.17 (q, J = 7.0 Hz, 2H), 3.87 (s, 3H), 2.47 (ddd, J = 4.6, 6.4, 9.6 Hz, 1H), 1.82 (ddd, J = 4.6, 5.6, 8.8 Hz, 1H), 1.54 (ddd, J = 4.8, 5.6, 9.2 Hz, 1H), 1.28 (t, J = 7.1 Hz, 3H)1.25 (ddd, buried, 1H) | 125 MHz, CDCl3 | 173.6, 146.5, 144.3, 131.9, 118.8, 114.3, 109.4, 60.7, 55.9, 26.1, 23.8, 16.7, 14.3 | 0.352902 | 17,912,370 | PLoS One. 2007 Oct 3; 2(10):e993 | PLoS One | 2,007 | CC BY | 2021-01-05 15:29:41 | no |
PMC1994063 | Xylosylfructoside The 1D 1H and 13C NMR spectra of xylosylfructoside showed anomeric proton (δH 5.34 ppm, d, 3.7 Hz) and carbon (δC 93.17 ppm) signals for the xylopyranosyl residue. The 1H-1H coupling constant value between H-1-Xyl (δH 5.34 ppm, d, J = 3.7 Hz) and H-2-Xyl (δH 3.53 ppm, dd, J = 10.0 and 3.7 Hz) determin... | xylosylfructoside | OCC1([C@H]([C@@H]([C@@H](CO)O1)O)O)OC2[C@@H]([C@H]([C@@H](CO)O2)O)O | The 1D 1H and 13C NMR spectra of xylosylfructoside showed anomeric proton (δH 5.34 ppm, d, 3.7 Hz) and carbon (δC 93.17 ppm) signals for the xylopyranosyl residue. The 1H-1H coupling constant value between H-1-Xyl (δH 5.34 ppm, d, J = 3.7 Hz) and H-2-Xyl (δH 3.53 ppm, dd, J = 10.0 and 3.7 Hz) determined the α-form of t... | The 1D 1H and 13C NMR spectra of xylosylfructoside showed anomeric proton (δH 5.34 ppm, d, 3.7 Hz) and carbon (δC 93.17 ppm) signals for the xylopyranosyl residue. The 1H-1H coupling constant value between H-1-Xyl (δH 5.34 ppm, d, J = 3.7 Hz) and H-2-Xyl (δH 3.53 ppm, dd, J = 10.0 and 3.7 Hz) determined the α-form of t... | null | 5.34, 3.53, 10.0, 3.7, 5.34, 104.55 | null | 93.17, 104.55 | 0.05955 | 17,880,747 | Chem Cent J. 2007 Jun 28; 1:18 | Chem Cent J | 2,007 | CC BY | 2021-01-04 23:56:43 | no |
PMC1994063 | Saccharide 1 The 1D 1H and 13C NMR spectra of saccharide 1 showed two anomeric proton (δH 5.11 ppm, d, 3.8 Hz and δH 5.59 ppm, d, 3.5 Hz) and carbon (δC 97.52 ppm and δC 90.84 ppm) signals for the xylopyranosyl and glucopyranosyl residues. The 1H-1H coupling constant between H-1 (δH 5.59 ppm, d, J = 3.5) and H-2 (δH 3.... | saccharide 1 | null | The 1D 1H and 13C NMR spectra of saccharide 1 showed two anomeric proton (δH 5.11 ppm, d, 3.8 Hz and δH 5.59 ppm, d, 3.5 Hz) and carbon (δC 97.52 ppm and δC 90.84 ppm) signals for the xylopyranosyl and glucopyranosyl residues. The 1H-1H coupling constant between H-1 (δH 5.59 ppm, d, J = 3.5) and H-2 (δH 3.65 ppm, d, J ... | The 1D 1H and 13C NMR spectra of saccharide 1 showed two anomeric proton (δH 5.11 ppm, d, 3.8 Hz and δH 5.59 ppm, d, 3.5 Hz) and carbon (δC 97.52 ppm and δC 90.84 ppm) signals for the xylopyranosyl and glucopyranosyl residues | null | 5.11, 5.59 | null | 97.52, 90.84 | 0.079301 | 17,880,747 | Chem Cent J. 2007 Jun 28; 1:18 | Chem Cent J | 2,007 | CC BY | 2021-01-04 23:56:43 | no |
PMC2071920 | Synthesis of Bio-ITC [4-(4-Isothiocyanato-butyl)-tetrahydro-thieno[3,4-d]imidazol-2-one] A solution of norbiotinamine hydrochloride (10 mg, 0.040 mmol) dissolved in acetonitrile (2 mL) and chloroform (0.40 mL) was prepared in a flame dried flask under Ar(g). A solution of TCDP (10 mg, 0.040 mmol) in chloroform (0.40 mL... | Bio-ITC | null | 1H NMR (300 MHz, CD3OD, 23°C, δ): 4.50 (dd, J = 7.9, 5.1 Hz, 1 H), 4.33 (dd, J = 7.1, 4.5 Hz, 1 H), 3.58 (t, J = 6.5 Hz, 2 H), 2.95 (dd, J = 12.8, 5.1 Hz, 1 H), 2.72 (d, J = 12.8 Hz, 1 H), 1.83–1.52 (m, 6 H) ppm | 13C NMR (300 MHz, CD3OD, 23°C, δ): 168.30, 125.85, 63.41, 61.63, 56.90, 41.05, 31.00, 29.08, 27.33 ppm | 300 MHz, CD3OD, 23°C, δ | 4.50 (dd, J = 7.9, 5.1 Hz, 1 H), 4.33 (dd, J = 7.1, 4.5 Hz, 1 H), 3.58 (t, J = 6.5 Hz, 2 H), 2.95 (dd, J = 12.8, 5.1 Hz, 1 H), 2.72 (d, J = 12.8 Hz, 1 H), 1.83–1.52 (m, 6 H) | 300 MHz, CD3OD, 23°C, δ | 168.30, 125.85, 63.41, 61.63, 56.90, 41.05, 31.00, 29.08, 27.33 | 0.336089 | 17,894,894 | BMC Cancer. 2007 Sep 25; 7:183 | BMC Cancer | 2,007 | CC BY | 2021-01-04 16:46:16 | no |
PMC2157549 | Fig. 4 Glycosyl linkage analysis of LM from C. glutamicum and Cg-t-LM from C. glutamicumΔmptA. Per-O-methylated samples were hydrolysed using 2 M trifluoroacetic acid, reduced and per-O-acetylated. The resulting partially per-O-methylated, per-O-acetylated alditol acetates from C. glutamicum LM (A) and C. glutamicumΔmp... | Cg-t-LM | null | The Cg-t-LM from C. glutamicumΔmptA possessed the same spin systems (Fig. 6C and D) as Cg-LM (Fig. 6A and B) and their anomeric resonances were attributed as follows: δH1C1 5.12/101.2 (I1) to 2,6-Manp, 5.05/105.2 (II1) to t-Manp, 5.00/104.9 (III1) to 2-Manp and 4.92/102.6 (VII1) to 6-Manp units respectively. The intens... | The Cg-t-LM from C. glutamicumΔmptA possessed the same spin systems (Fig. 6C and D) as Cg-LM (Fig. 6A and B) and their anomeric resonances were attributed as follows: δH1C1 5.12/101.2 (I1) to 2,6-Manp, 5.05/105.2 (II1) to t-Manp, 5.00/104.9 (III1) to 2-Manp and 4.92/102.6 (VII1) to 6-Manp units respectively. The intens... | null | 5.12/101.2 (I1) to 2,6-Manp, 5.05/105.2 (II1) to t-Manp, 5.00/104.9 (III1) to 2-Manp, 4.92/102.6 (VII1) to 6-Manp | null | 5.12/101.2, 5.05/105.2, 5.00/104.9, 4.92/102.6 | 0.00105 | 17,714,444 | Mol Microbiol. 2007 Sep; 65(6):1503-1517 | Mol Microbiol | 2,007 | CC BY | 2021-03-16 23:20:14 | no |
PMC2174954 | Godschalk PC Heikema AP Gilbert M Komagamine T Ang CW Glerum J Brochu D Li J Yuki N Jacobs BC van BA Endtz HP The crucial role of Campylobacter jejuni genes in anti-ganglioside antibody induction in Guillain-Barré syndrome J Clin Invest 2004 114 1659 1665 15578098 10.1172/JCI200415707 Koga M Gilbert M Takahashi M Li J... | nanomole amounts | null | nanomole amounts by 600-mhz 1H and 13C NMR analysis | nanomole amounts by 600-mhz 1H and 13C NMR analysis | 600-mhz | nanomole amounts | nanomole amounts by 600-mhz 1H and 13C NMR analysis | nanomole amounts | 0.023428 | 17,919,333 | BMC Genomics. 2007 Oct 5; 8:359 | BMC Genomics | 2,007 | CC BY | 2021-01-04 16:49:06 | no |
PMC2176056 | Results and Discussion The cycloaddition of TosMIC 2 to 3,3-di(methylsulfanyl)-1-phenyl-2-propen-1-one 1a was taken as a test case to evaluate the cycloaddition and to arrive at the optimal reaction conditions. The cycloaddition of 2 to 1a took place smoothly in the presence of NaH in THF at rt to furnish [5-[(4-methyl... | [5-[(4-methylphenyl)sulfonyl]-4-(methylsulfanyl)-1H-3-pyrrolyl](phenyl)methanone | O=C(C1=CNC(S(=O)(C2=CC=C(C)C=C2)=O)=C1SC)C3=CC=CC=C3 | The cycloaddition of TosMIC 2 to 3,3-di(methylsulfanyl)-1-phenyl-2-propen-1-one 1a was taken as a test case to evaluate the cycloaddition and to arrive at the optimal reaction conditions. The cycloaddition of 2 to 1a took place smoothly in the presence of NaH in THF at rt to furnish [5-[(4-methylphenyl)sulfonyl]-4-(met... | As anticipated the 13C NMR spectrum of 3a displayed fifteen signals, with a diagnostic signal at δ 127.9 ppm assignable to pyrrole C-5 | null | 2.23, 2.42 | null | 127.9 | 0.045717 | 17,903,258 | Beilstein J Org Chem. 2007 Sep 28; 3:31 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:55 | no |
PMC2213660 | Scheme 6 Alkylation of ketal-ester 12. Surprisingly, alkylation of ketal-ester 12 using NaH in dry DMF proceeded smoothly even at room temperature, however it resulted in an unusual cleavage of ethylene ketal under basic conditions, leading to hydroxy vinylether 13 in 70% yield. The formation of hydroxy vinylether 13 i... | hydroxy vinylether | C=CO(O)C=C | The presence of a sharp singlet at δH 5.66 (s,1H) in 1H NMR and signals corresponding to vinyl carbons (δc 104.28, 164.39) in 13C NMR, as well as an absorption at 3513 cm-1 in IR spectrum, clearly indicate the presence of a vinylether and a free hydroxyl group in compound 13 | The presence of a sharp singlet at δH 5.66 (s,1H) in 1H NMR and signals corresponding to vinyl carbons (δc 104.28, 164.39) in 13C NMR, as well as an absorption at 3513 cm-1 in IR spectrum, clearly indicate the presence of a vinylether and a free hydroxyl group in compound 13 | null | 5.66 (s,1H) | null | 104.28, 164.39 | 0.310544 | 18,088,442 | Beilstein J Org Chem. 2007 Dec 19; 3:49 | Beilstein J Org Chem | 2,007 | CC BY | 2021-02-20 23:14:55 | no |
PMC2225588 | the resulting residue was purified by chromatography on silica gel (4% MeOH in CH2Cl2 eluant) to yield the tosylate 3 (63 g, 87%) as a colorless viscous oil: 1H NMR (500 MHz, CDCl3) δ 2.43 (s, 3H, ArCH3), 3.35 (s, 3H, OCH3), 3.52 (t, 2H, CH2), 3.50−3.60 (m, 10H, CH2), 3.67 (t, 2H, CH2), 4.14 (t, 2H, CH2), 7.33 (d, 2H, ... | tosylate | OS(=O)(C1=CC=C(C)C=C1)=O | 1H NMR (500 MHz, CDCl3) δ 2.43 (s, 3H, ArCH3), 3.35 (s, 3H, OCH3), 3.52 (t, 2H, CH2), 3.50−3.60 (m, 10H, CH2), 3.67 (t, 2H, CH2), 4.14 (t, 2H, CH2), 7.33 (d, 2H, ArH), 7.78 (d, 2H, ArH) | 13C NMR (125 MHz, CDCl3) 21.8, 59.1, 68.8, 69.4, 70.6, 70.8, 71.2, 71.6, 71.9, 72.2, 128.1, 130.0, 133.1, 145.0 | 500 MHz, CDCl3 | 2.43 (s, 3H, ArCH3), 3.35 (s, 3H, OCH3), 3.52 (t, 2H, CH2), 3.50−3.60 (m, 10H, CH2), 3.67 (t, 2H, CH2), 4.14 (t, 2H, CH2), 7.33 (d, 2H, ArH), 7.78 (d, 2H, ArH) | 125 MHz, CDCl3 | 21.8, 59.1, 68.8, 69.4, 70.6, 70.8, 71.2, 71.6, 71.9, 72.2, 128.1, 130.0, 133.1, 145.0 | 0.710702 | 18,274,661 | Met Based Drugs. 2008 Oct 1; 2008:391418 | Met Based Drugs | 2,008 | CC BY | 2021-01-05 11:32:13 | no |
PMC2225588 | (80 mL) at reflux under a nitrogen atmosphere for 12 hours. The solvent was then removed under reduced pressure, and the resulting residue was purified by chromatography on silica gel (4% MeOH in CH2Cl2 eluant) to yield 4 (13.40 g, 64%) as a viscous yellow oil: 1H NMR (500 MHz, CDCl3) δ 3.30 (t, 4H, CH2), 3.56 (s, 6H, ... | 4 | null | 1H NMR (500 MHz, CDCl3) δ 3.30 (t, 4H, CH2), 3.56 (s, 6H, OCH3), 3.50 (t, 4H, CH2), 3.53 (t, 4H, CH2), 3.58 (t, 4H, CH2), 3.62 ∼ 3.64 (m, 8H, CH2), 3.65 (t, 4H, CH2), 3.74 (t, 4H, CH2) | 13C NMR (125 MHz, CDCl3) 21.8, 59.1, 68.8, 69.4, 70.7, 70.8, 71.3, 71.7, 72.0, 73.2, 128.1 | 500 MHz, CDCl3 | 3.30 (t, 4H, CH2), 3.56 (s, 6H, OCH3), 3.50 (t, 4H, CH2), 3.53 (t, 4H, CH2), 3.58 (t, 4H, CH2), 3.62 ∼ 3.64 (m, 8H, CH2), 3.65 (t, 4H, CH2), 3.74 (t, 4H, CH2) | 125 MHz, CDCl3 | 21.8, 59.1, 68.8, 69.4, 70.7, 70.8, 71.3, 71.7, 72.0, 73.2, 128.1 | 0.886505 | 18,274,661 | Met Based Drugs. 2008 Oct 1; 2008:391418 | Met Based Drugs | 2,008 | CC BY | 2021-01-05 11:32:13 | no |
PMC2225588 | green. After 2 hours, the reaction mixture was a deep blue color. Heating and stirring were continued for a total 7 hours after which the solvent was removed under reduced pressure. The resulting residue was dissolved in CH2Cl2 (20 mL). TFA (2 mL) was slowly added, and the solution was stirred for 1 hour. After dilutio... | 5 | null | 1H NMR (500 MHz, CDCl3) δ-1.13 (br s, 2H, NH), 3.32 (s, 24H, –OCH3), 3.40 (t, 16H, CH2), 3.55 ∼ 3.59 (m, 64H, CH2), 3.65 (t, 16H, CH2), 3.99 (t, 16H, CH2), 4.28 (t, 16H, CH2) | 13C NMR (125 MHz, CDCl3) 34.76, 59.23, 70.68, 70.72, 70.74, 70.77, 71.11, 72.09, 140.56 | 500 MHz, CDCl3 | 1.13 (br s, 2H, NH), 3.32 (s, 24H, –OCH3), 3.40 (t, 16H, CH2), 3.55 ∼ 3.59 (m, 64H, CH2), 3.65 (t, 16H, CH2), 3.99 (t, 16H, CH2), 4.28 (t, 16H, CH2) | 125 MHz, CDCl3 | 34.76, 59.23, 70.68, 70.72, 70.74, 70.77, 71.11, 72.09, 140.56 | 0.595604 | 18,274,661 | Met Based Drugs. 2008 Oct 1; 2008:391418 | Met Based Drugs | 2,008 | CC BY | 2021-01-05 11:32:13 | no |
PMC2225588 | 2.7. 19,22-bis(1-Methylethoxy)-4,5,9,10,14,15-hexakis{2-{2-[2-(2-methoxyethoxy)ethoxy]-ethoxy}ethylthio}-23H,25H-porphyrazine (6) UV-vis (CH2Cl2) λmax (log ɛ) 350 (4.61), 658 (3.82), 702 (4.35), 744 (sh) nm; 1H NMR (500 MHz, CDCl3) δ-0.20 (br s, 2H, NH), 2.02 (d, 12H, –CHMe3), 3.69 (s, 18H, OCH3), 3.76 ∼ 3.79 (m, 48H,... | 19,22-bis(1-Methylethoxy)-4,5,9,10,14,15-hexakis{2-{2-[2-(2-methoxyethoxy)ethoxy]-ethoxy}ethylthio}-23H,25H-porphyrazine | null | 1H NMR (500 MHz, CDCl3) δ-0.20 (br s, 2H, NH), 2.02 (d, 12H, –CHMe3), 3.69 (s, 18H, OCH3), 3.76 ∼ 3.79 (m, 48H, CH2), 3.84 ∼ 3.87 (m, 24H, CH2), 4.02 (t, 4H, CH2), 4.17 (t, 4H, CH2), 4.19 (t, 4H, CH2), 4.39 (t, 4H, CH2), 4.46 (t, 4H, CH2), 4.51 (t, 4H, CH2), 5.49 (sept, 2H, –CHMe2), 7.87 (s, 2H, ArH) | 13C NMR (125 MHz, CDCl3) 22.3, 22.4, 22.7, 22.9, 29.9, 34.7, 34.8, 34.9, 36.5, 59.2, 70.6, 70.7, 70.8, 71.1, 71.2, 72.1, 72.7, 119.6, 126.5, 138.4, 138.8, 141.9, 150.5 | 500 MHz, CDCl3 | -0.20 (br s, 2H, NH), 2.02 (d, 12H, –CHMe3), 3.69 (s, 18H, OCH3), 3.76 ∼ 3.79 (m, 48H, CH2), 3.84 ∼ 3.87 (m, 24H, CH2), 4.02 (t, 4H, CH2), 4.17 (t, 4H, CH2), 4.19 (t, 4H, CH2), 4.39 (t, 4H, CH2), 4.46 (t, 4H, CH2), 4.51 (t, 4H, CH2), 5.49 (sept, 2H, –CHMe2), 7.87 (s, 2H, ArH) | 125 MHz, CDCl3 | 22.3, 22.4, 22.7, 22.9, 29.9, 34.7, 34.8, 34.9, 36.5, 59.2, 70.6, 70.7, 70.8, 71.1, 71.2, 72.1, 72.7, 119.6, 126.5, 138.4, 138.8, 141.9, 150.5 | 0.620624 | 18,274,661 | Met Based Drugs. 2008 Oct 1; 2008:391418 | Met Based Drugs | 2,008 | CC BY | 2021-01-05 11:32:13 | no |
PMC2225981 | 3)2)2N(CH3)). 13C NMR (δ ppm CDCl3, 125 MHz, proton decoupled): 138, 135, 132, 126, 121, 119, 108 [C 5H4 and C 4H(CH2–N(CH3)2)2N(CH3)]; 52 [C5H4–CH–(N(CH3)2)(C4H(CH2–N(CH3)2)2N(CH3)]; 34, 32 [N(CH3)2 and C4H(CH2–N(CH3)2)2N(CH3)]. | 2)2N(CH3) | null | null | 13C NMR (δ ppm CDCl3, 125 MHz, proton decoupled): 138, 135, 132, 126, 121, 119, 108 [C 5H4 and C 4H(CH2–N(CH3)2)2N(CH3)]; 52 [C5H4–CH–(N(CH3)2)(C4H(CH2–N(CH3)2)2N(CH3)]; 34, 32 [N(CH3)2 and C4H(CH2–N(CH3)2)2N(CH3)] | null | null | CDCl3, 125 MHz, proton decoupled | 138, 135, 132, 126, 121, 119, 108, 52, 34, 32 | 0.273824 | 18,274,663 | Met Based Drugs. 2008 Oct 1; 2008:754358 | Met Based Drugs | 2,008 | CC BY | 2021-01-05 11:32:14 | no |
PMC2225981 | 3)2)]. 13C NMR (δ ppm CDCl3, 125 MHz, proton decoupled): 146, 138, 136, 132, 131, 129, 127, 124, 120 [(C 6H4 CH2N(CH3)2) and (C 5H4)]; 61 [C5H4–CH–(N(CH3)2 (C6H4CH2N(CH3)2))]; 60 [(C6H4 CH2N(CH3)2)]; 42 [C5H4–CH–(N(CH3)2(C6H4CH2N(CH3)2))]. | (C 5H4) and (C 6H4 CH2N(CH3)2) | null | null | 146, 138, 136, 132, 131, 129, 127, 124, 120 [(C 6H4 CH2N(CH3)2) and (C 5H4)]; 61 [C5H4–CH–(N(CH3)2 (C6H4CH2N(CH3)2)]; 60 [(C6H4 CH2N(CH3)2)]; 42 [C5H4–CH–(N(CH3)2(C6H4CH2N(CH3)2)] | null | null | CDCl3, 125 MHz, proton decoupled | 146, 138, 136, 132, 131, 129, 127, 124, 120 [(C 6H4 CH2N(CH3)2) and (C 5H4)]; 61 [C5H4–CH–(N(CH3)2 (C6H4CH2N(CH3)2)]; 60 [(C6H4 CH2N(CH3)2)]; 42 [C5H4–CH–(N(CH3)2(C6H4CH2N(CH3)2)] | 0.001789 | 18,274,663 | Met Based Drugs. 2008 Oct 1; 2008:754358 | Met Based Drugs | 2,008 | CC BY | 2021-01-05 11:32:14 | no |
PMC2248282 | O-(2,4-Dimethoxybenzyl)hydroxylamine (11b). N-(2,4-dimethoxybenzyloxy)phthalamide 10b (1.83 g, 5,84 mmol) was stirred as a suspension in 60 mL of refluxing ethanol. N-methylhydrazine (0.34 mL, 6.4 mmol) was added, and the mixture was stirred at reflux for 1 h. The solution was concentrated to remove the ethanol. Ether ... | O-(2,4-Dimethoxybenzyl)hydroxylamine | NOCC1=CC=C(OC)C=C1OC | 1H NMR (500 MHz, CDCI3): δ=3.77 (3H, s, OCH3), 3.78 (3H, s, OCH3), 4.64 (2H, s, CH2), 5.41 (2H, bs, NH2), 6.43–6.44 (2H, m, Ar-H), 7.19–7.22 ppm (1H, m, Ar-H) | 13C NMR (125 MHz, CDCl3): δ=24.3 (C(CH3)2), 26.6 (C(CH3)2), 55.46 (OCH3), 55.58 (OCH3), 61.4 (CHCH2OH), 73.6 (ArCH2), 76.5 (CHCH2OH), 77.6 (COCHCH), 98.6 (CH-Ar), 104.2 (CH-Ar), 110.2 (C(CH3)2), 115.5 (C-Ar), 132.9 (CH-Ar), 159.5 (CH3OC-Ar), 161.9 (CH3OC-Ar), 167.1 ppm (NHCOCH) | 500 MHz, CDCI3 | 3.77 (3H, s, OCH3), 3.78 (3H, s, OCH3), 4.64 (2H, s, CH2), 5.41 (2H, bs, NH2), 6.43–6.44 (2H, m, Ar-H), 7.19–7.22 (1H, m, Ar-H) | 125 MHz, CDCl3 | 24.3, 26.6, 55.46, 55.58, 61.4, 73.6, 76.5, 77.6, 98.6, 104.2, 110.2, 115.5, 132.9, 159.5, 161.9, 167.1 | 0.252276 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-thiopropionic acid S-(2-hydroxy-ethyl) ester (13). Pivaloyl chloride (3.2 mL, 26 mmol) was added to a stirred solution of 2-mercaptoethanol (1.8 mL, 26 mmol) and triethylamine (3.6 mL, 26 mmol) in CH2Cl2, cooled at −78°C. The mixture was stirred at −78°C for 1 h, then allowed to warm to room temperature an... | 2,2-Dimethyl-thiopropionic acid S-(2-hydroxy-ethyl) ester | CC(C)(C)C(SCCO)=O | 1H NMR (500 MHz, CDCl3): δ=1.23 (9H, s, C(CH3)3), 2.62 (1H, bs, OH), 3.04 (2H, t, J=6.1 Hz SCH2), 3.72 ppm (2H, t, J=6.1, OCH2) | 13C NMR (125 MHz, CDCl3): δ=27.8 (CH3), 31.9 (SCH2), 47.0 (CMe3), 63.2 (OCH2), 207.7 ppm (SCO) | 500 MHz, CDCl3 | 1.23 (9H, s, C(CH3)3), 2.62 (1H, bs, OH), 3.04 (2H, t, J=6.1 Hz SCH2), 3.72 ppm (2H, t, J=6.1, OCH2) | 125 MHz, CDCl3 | 27.8, 31.9, 47.0, 63.2, 207.7 | 0.416134 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-thiopropionic acid S-[2-(chloro-phenoxy-phosphoryloxy)-ethyl] ester (5a). Dichloro phenyl phosphonate (1.06 g, 5 mmol) was added dropwise into a cooled solution (−78°C) of 13 (0.81 g, 5 mmol) and TEA (0.70 mL, 5 mmol) in THF (20 mL). The reaction was left to warm to room temperature and stirred overnight. ... | 2,2-Dimethyl-thiopropionic acid S-[2-(chloro-phenoxy-phosphoryloxy)-ethyl] ester | CC(C)(C)C(SCCOP(OC1=CC=CC=C1)(Cl)=O)=O | 1H NMR (500 MHz, CDCl3): δ=1.25 (9H, s, C(CH3)3), 3.24 (2H, t, J=6.4 Hz, CH2CH2S), 4.34–4.41 (2H, m, CH2CH2OP), 7.25–7.28 (3H, m, Ph-H), 7.39 ppm (2H, t, J=7.9 Hz, Ph-H) | 13C NMR (125 MHz, CDCl3): δ=27.3 (C(CH3)3), 28.2, 28.1 (CH2S), 46.5 (C(CH3)3), 68.2 (d, J=7.20 Hz, CH2O), 120.3 (d, J=5.3 Hz, orto-CH-Ar), 126.3 (meta-CH-Ar), 130.0 (para-CH-Ar), 149.7 (d, J=8.9 Hz, C-Ar), 205.6 ppm (SCO) | 500 MHz, CDCl3 | 1.25 (9H, s, C(CH3)3), 3.24 (2H, t, J=6.4 Hz, CH2CH2S), 4.34–4.41 (2H, m, CH2CH2OP), 7.25–7.28 (3H, m, Ph-H), 7.39 ppm (2H, t, J=7.9 Hz, Ph-H) | 125 MHz, CDCl3 | 27.3, 28.2, 28.1, 46.5, 68.2, 120.3, 126.3, 130.0, 149.7, 205.6 | 0.664738 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-thiopropionic acid S-(2-{[5-(4-methoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphoryloxy}-ethyl) ester (26a). Compound 4a (100 mg, 0.32 mmol) was dissolved in dry DCM (4.5 mL) and was added into a solution of 13 (151 mg, 0.45 mmol) in dry DCM (2.5 mL). The mixture was cooled... | 2,2-Dimethyl-thiopropionic acid S-(2-{[5-(4-methoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphoryloxy}-ethyl) ester | CC(C)(C)C(OCCOP(OC1=CC=CC=C1)(OCC2OC(C)(C)O[C@@H]2C(NOCC3=CC=C(OC)C=C3)=O)=O)=S | 1H NMR (500 MHz, CDCl3): δ=1.14, 1.15 (9H, 2 s, C(CH3)3), 1.25, 1.26 (3H, 2 s, C(CH3)2), 1.34, 1,36 (3H, 2 s, C(CH3)2), 3.06 (2H, d, J=6.7 Hz, CH2S), 3.73 (3H, s, OCH3), 4.06–4.16 (3H, m, CHHOP+OCH2CH2S), 4.42–4.56 (3H, m, CHCH+CHCH+CHCHHOP), 4.74–4.83 (2H, m, ArCH2), 6.82 (2H, dd, J1=1.6 Hz, J2=8.7 Hz, Ar-H), 7.09 (1H... | 13C NMR (125 MHz, CDCl3): δ=24.5, 25.5 (CCH3), 26.5, 26.6 (CCH3), 27.0, 27.3 (C(CH3)3), 28.4, 28.5 (CH2S), 55.3 (OCH3), 66.66, 66.69, 66.71, 66.76 (CHCH2OP + POCH2CH2S), 74.9, 75.0 (CHCH2OP), 75.8, 75.9 (COCHCH), 78.2 (ArCH2O), 110.7 (C(CH3)2), 113.9, 114.0 (Ph-CH), 120.1, 120.2 (Ph-CH), 125.2 (Ar-C), 126.78, 126.86 (P... | 500 MHz, CDCl3 | 1.14, 1.15 (9H, 2 s, C(CH3)3), 1.25, 1.26 (3H, 2 s, C(CH3)2), 1.34, 1,36 (3H, 2 s, C(CH3)2), 3.06 (2H, d, J=6.7 Hz, CH2S), 3.73 (3H, s, OCH3), 4.06–4.16 (3H, m, CHHOP+OCH2CH2S), 4.42–4.56 (3H, m, CHCH+CHCH+CHCHHOP), 4.74–4.83 (2H, m, ArCH2), 6.82 (2H, dd, J1=1.6 Hz, J2=8.7 Hz, Ar-H), 7.09 (1H, t, J=7.3 Hz, Ph-H), 7.15–... | 125 MHz, CDCl3 | 24.5, 25.5, 26.5, 26.6, 27.0, 27.3, 28.4, 28.5, 55.3, 66.66, 66.69, 66.71, 66.76, 74.9, 75.0, 75.8, 75.9, 78.2, 110.7, 113.9, 114.0, 120.1, 120.2, 125.2, 126.78, 126.86, 129.70, 131.1, 150.44, 150.50, 160.1, 165.5, 205.7 | 0.734953 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-thiopropionic acid S-(2-{[5-(2,4-dimethoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphoryloxy}-ethyl) ester (26b). NMI (0.07 mL, 0.87 mmol) was added into a cooled solution (−78°C) of 4b (100 mg, 0.29 mmol) and 13 (140 mg, 0.41 mmol) in anhydrous DCM (7 mL). The reaction was ... | 2,2-Dimethyl-thiopropionic acid S-(2-{[5-(2,4-dimethoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphoryloxy}-ethyl) ester | CC(C)(C)C(OCCOP(OC1=CC=CC=C1)(OCC2OC(C)(C)O[C@@H]2C(NOCC3=CC=C(OC)C=C3OC)=O)=O)=S | 1H NMR (500 MHz, CDCl3): δ=1.14, 1.145 (9H, 2 s, C(CH3)3), 1.26, 1.27 (3H, 2 s, C(CH3)2), 1.37, 1.39 (3H, 2 s, C(CH3)2), 3.05 (2H, t, J=6.7 Hz, CH2S), 3.73 (3H, s, OCH3), 3.75 (3H, s, OCH3), 4.10–4.15 (3H, m, OCH2CH2S + CHCHHOP), 4.43–4.57 (3H, m, COCH + CHCHCH2OP + CHCHHOP), 4.80–4.87 (2, m, ArCH2), 6.39–6.43 (2H, m, ... | 13C NMR (125 MHz, CDCl3): δ=24.5 (C(CH3)2), 26.68, 26.71 (C(CH3)2), 27.3 (C(CH3)3), 28.43, 28.48 (CH2S), 55.4, 55.5 (OCH3), 66.6, 66.7, 66.8, 66.9 (CHCH2OP + POCH2CH2S), 73.5, 73.6 (ArCH2), 74.95, 74.98 (CHCH2OP), 75.89, 75.94 (COCHCH), 98.6 (Ar-CH), 104.1 (Ar-CH), 110.4 (C(CH3)2), 120.1, 120.2 (Ph-CH), 125.1 (Ph-CH), ... | 500 MHz, CDCl3 | 1.14, 1.145 (9H, 2 s, C(CH3)3), 1.26, 1.27 (3H, 2 s, C(CH3)2), 1.37, 1.39 (3H, 2 s, C(CH3)2), 3.05 (2H, t, J=6.7 Hz, CH2S), 3.73 (3H, s, OCH3), 3.75 (3H, s, OCH3), 4.10–4.15 (3H, m, OCH2CH2S + CHCHHOP), 4.43–4.57 (3H, m, COCH + CHCHCH2OP + CHCHHOP), 4.80–4.87 (2, m, ArCH2), 6.39–6.43 (2H, m, Ph-H), 7.13–7.26 (5H, m, Ph... | 125 MHz, CDCl3 | 24.5, 26.68, 26.71, 27.3, 28.43, 28.48, 55.4, 55.5, 66.6, 66.7, 66.8, 66.9, 73.5, 73.6, 74.95, 74.98, 75.89, 75.94, 98.6, 104.1, 110.4, 120.1, 120.2, 125.1, 129.7, 132.9 | 0.267631 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-thiopropionic acid S-(2-{[5-(2,4-dimethoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphoryloxy}-ethyl) ester (3d). 26b (115 mg, 0.18 mmol) was dissolved in a solution of 5% TFA in DCM (2 mL) and stirred at room temperature. After 15 min the colourless solution became deep purp... | 2,2-Dimethyl-thiopropionic acid S-(2-{[5-(2,4-dimethoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphoryloxy}-ethyl) ester | CC(C)(C)C(OCCOP(OC1=CC=CC=C1)(OCC2OC(C)(C)O[C@@H]2C(NOCC3=CC=C(OC)C=C3OC)=O)=O)=S | 1H NMR (500 MHz, CDCl3): δ=1.15 (9H, s, C(CH3)3), 1.28 (3H, s, C(CH3)2),1.44, 1.45 (3H, 2 s, C(CH3)2), 3.07 (2H, dd, J=12.4, 6.4 Hz, CH2S), 4.09–4.22 (3H, m, CH2CH2S + CHCHHOP), 4.29–4.34 (1H, m, CHHOP), 4.52 (1H, bs, CHCH2OP), 4.66 (1H, d, J=7.6 Hz, COCHCH), 7.09–7.16 (3H, m, Ph-H), 7.27 (2H, t, J=7.9 Hz, Ph-H), 9.00,... | 13C NMR (125 MHz, CDCl3): δ=24.55, 24.57 (C(CH3)2), 26.63, 26.68 (C(CH3)2), 27.3 (C(CH3)3), 28.33, 28.41 (CH2S), 66.53, 66.58, 66.69, 66.74, 66.87, 66.92, 67.13, 67.17 (CH2OP + CH2CH2S), 74.68, 74.79 (CHCH2OP), 75.75, 75.80 (COCHCH), 111.5 (C(CH3)2), 120.10, 120.17 (Ph-CH), 125.36, 125.41 (Ph-CH), 129.79 (Ph-CH), 150.4... | 500 MHz, CDCl3 | 1.15 (9H, s, C(CH3)3), 1.28 (3H, s, C(CH3)2),1.44, 1.45 (3H, 2 s, C(CH3)2), 3.07 (2H, dd, J=12.4, 6.4 Hz, CH2S), 4.09–4.22 (3H, m, CH2CH2S + CHCHHOP), 4.29–4.34 (1H, m, CHHOP), 4.52 (1H, bs, CHCH2OP), 4.66 (1H, d, J=7.6 Hz, COCHCH), 7.09–7.16 (3H, m, Ph-H), 7.27 (2H, t, J=7.9 Hz, Ph-H), 9.00, 9.09 ppm (1H, 2 s, NH) | 125 MHz, CDCl3 | 24.55, 24.57, 26.63, 26.68, 27.3, 28.33, 28.41, 66.53, 66.58, 66.69, 66.74, 66.87, 66.92, 67.13, 67.17, 74.68, 74.79, 75.75, 75.80, 111.5, 120.10, 120.17, 125.36, 125.41, 129.79, 150.4, 165.2, 205.9 | 0.661252 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-thiopropionic acid S-(2-{diisopropylamino-[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-phosphanyloxy}-ethyl) ester (6a). A solution of S-pivaloyl thioethanol 13 (1.62 g, 10 mmol) and triethylamine (3.06 mL, 22 mmol) in THF (35 mL) was added dropwise over 1.5 h at −78°C into a solution of diisopropylamino di... | 2,2-Dimethyl-thiopropionic acid S-(2-{diisopropylamino-[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-phosphanyloxy}-ethyl) ester | CC(C)(C)C(OCCO[P@](N(C(C)C)C(C)C)OCCSC(C(C)(C)C)=O)=S | 1H NMR (500 MHz, CDCl3): δ=1.09, 1.10 (12H, 2 s, 2×CH(CH3)2), 1.16, 1.17 (18H, 2 s, 2×C(CH3)3), 3.00–3.06 (4H, m, 2×CH2S), 3.46–3.71 ppm (6H, m, 2×(CH2O) + 2×(CH(CH3)2) | 13C NMR (125 MHz, CDCl3): δ=24.6 (C(CH3)2), 26.7 (C(CH3)2), 27.3 (C(CH3)3), 28.5, 28.55 (CH2S), 46.5 (C(CH3)3), 55.4, 55.6 (OCH3), 66.1, 66.2, 66.3 (POCH2 + CHCH2OP), 73.5 (ArCH2), 75.0 (CHCH2OP), 75.96, 76.02 (COCH), 98.6 (Ar-CH). 104.2 (Ar-CH), 110.7 (C(CH3)2), 115.7 (Ar-CH), 132.9 (Ar-C), 159.4 (Ar-C), 161.8 (Ar-C),... | 500 MHz, CDCl3 | 1.09, 1.10 (12H, 2 s, 2×CH(CH3)2), 1.16, 1.17 (18H, 2 s, 2×C(CH3)3), 3.00–3.06 (4H, m, 2×CH2S), 3.46–3.71 (6H, m, 2×(CH2O) + 2×(CH(CH3)2) | 125 MHz, CDCl3 | 24.6, 26.7, 27.3, 28.5, 28.55, 46.5, 55.4, 55.6, 66.1, 66.2, 66.3, 73.5, 75.0, 75.96, 76.02, 98.6, 104.2, 110.7, 115.7, 132.9, 159.4, 161.8, 165.2, 205.7 | 0.191137 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-thiopropionic acid S-{2-[[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-(5-hydroxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phosphoryloxy]-ethyl} ester (3a). TFA (0.040 mL) was added into a solution of 27 (157 mg, 0.22 mmol) in DCM (4 mL). The reaction was stirred at room temperature until the complet... | 2,2-Dimethyl-thiopropionic acid S-{2-[[2-(2,2-dimethyl-propionylsulfanyl)-ethoxy]-(5-hydroxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phosphoryloxy]-ethyl} ester | CC(C)(C)C(OCCOP(OCC1OC(C)(C)O[C@@H]1C(NO)=O)(OCCSC(C(C)(C)C)=O)=O)=S | 1H NMR (500 MHz, CDCl3): δ=1.17, 1.17 (18H, 2 s, C(CH3)3), 1.30 (3H, s, C(CH3)2), 1.47 (3H, s, C(CH3)2), 3.06 (2H, t, J=6.8 Hz, CH2S), 3.09 (2H, t, J=6.7 Hz, CH2S), 4.00–4.05 (2H, m, CHCH2OP), 4.06–4.20 (4H, m, 2×POCH2CHS), 4.49–4.53 (1H, m, CHCH2OP), 4.68 (1H, d, J=7.5 Hz, COCH), 7.72 (1H, bs, OH), 8.90 ppm (1H, s, NH... | 13C NMR (125 MHz, CDCl3): δ=24.6 (C(CH3)2), 26.7 (C(CH3)2), 27.32, 27.33 (C(CH3)3), 28.4 (CH2S), 46.6 (C(CH3)3), 65.6, 66.36, 66.40, 66.75, 66.79 (CHCH2OP + POCH2), 74.96 (CHCH2OP), 75.85 (COCH), 110.7 (C(CH3)2), 165.25 ppm (HNCO) | 500 MHz, CDCl3 | 1.17, 1.17 (18H, 2 s, C(CH3)3), 1.30 (3H, s, C(CH3)2), 1.47 (3H, s, C(CH3)2), 3.06 (2H, t, J=6.8 Hz, CH2S), 3.09 (2H, t, J=6.7 Hz, CH2S), 4.00–4.05 (2H, m, CHCH2OP), 4.06–4.20 (4H, m, 2×POCH2CHS), 4.49–4.53 (1H, m, CHCH2OP), 4.68 (1H, d, J=7.5 Hz, COCH), 7.72 (1H, bs, OH), 8.90 ppm (1H, s, NH) | 125 MHz, CDCl3 | 24.6, 26.7, 27.32, 27.33, 28.4, 46.6, 65.6, 66.36, 66.40, 66.75, 66.79, 74.96, 75.85, 110.7, 165.25 | 0.835064 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2-{[5-(4-Methoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid methyl ester (25a). To a cooled (−78°C) solution of 4a (31 mg, 0.1 mmol) and 5c (111 mg, 0.4 mmol) in dry THF (2 mL), NMI (0.048 mL, 0.6 mmol) was added dropwise with a syringe over 1 min. The reaction w... | 2-{[5-(4-Methoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-phenoxy-phosphorylamino}-propionic acid methyl ester | CC(NP(OC1=CC=CC=C1)(OCC2OC(C)(C)OC2C(NOCC3=CC=C(OC)C=C3)=O)=O)C(OC)=O | 1H NMR (500 MHz, CDCl3): δ=1.28–1.41 (9H, m, CHCH3 + C(CH3)2), 3.69, 3.70 (3H, 2 s, CO2CH3), 3.81, 3.83 (3H, 2 s, PhOCH3), 4.05–4.20 (2H, m, CHCH3 + CHCHHOP), 4.41–4.50 (1H, m, CHCHHOP), 4.57–4.69 (2H, m, COCH + CHCH2OP), 4.88 (2H, s, ArCH2), 6.90 (2H, t, J=8.4 Hz, Ph-H), 7.12–7.16 (1H, m, Ph-H), 7.20–7.22 (2H, m, Ph-H... | 13C NMR (125 MHz, CDCl3): δ=20.9, 21.0, 21.1 (C(CH3)3), 24.5, 24.6 (C(CH3)2), 26.5, 26.7 (C(CH3)2), 49.9, 50.1 (CHCH3), 52.3, 52.4 (CO2CH3), 55.4, 55.5 (PhOCH3), 64.9, 65.0, 65.2, 65.24 (CH2OP), 73.5 (ArCH2), 74.9, 75.3 (CHCHCH2) 76.0, 76.11, (COCHCH), 98.5 (Ar-CH), 104.1 (Ar-CH), 120.27, 120.32, 120.36, 120.4 (Ph-CH),... | 500 MHz, CDCl3 | 1.28–1.41 (9H, m, CHCH3 + C(CH3)2), 3.69, 3.70 (3H, 2 s, CO2CH3), 3.81, 3.83 (3H, 2 s, PhOCH3), 4.05–4.20 (2H, m, CHCH3 + CHCHHOP), 4.41–4.50 (1H, m, CHCHHOP), 4.57–4.69 (2H, m, COCH + CHCH2OP), 4.88 (2H, s, ArCH2), 6.90 (2H, t, J=8.4 Hz, Ph-H), 7.12–7.16 (1H, m, Ph-H), 7.20–7.22 (2H, m, Ph-H), 7.27–7.38 (4H, m, Ar-H),... | 125 MHz, CDCl3 | 20.9, 21.0, 21.1, 24.5, 24.6, 26.5, 26.7, 49.9, 50.1, 52.3, 52.4, 55.4, 55.5, 64.9, 65.0, 65.2, 65.24, 73.5, 74.9, 75.3, 76.0, 76.11, 98.5, 104.1, 120.27, 120.32, 120.36, 120.4, 124.5, 124.7, 129.5, 129.6, 132.8 | 0.457481 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2-[(5-Hydroxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenoxy-phosphorylamino]-propionic acid methyl ester (3b). 25b (84 mg, 0.14 mmol) was dissolved in a solution of TFA 2% in DCM (2 mL). The reaction was stirred 15 min at room temperature; until the complete disappearance of the starting material was observe... | 2-[(5-Hydroxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenoxy-phosphorylamino]-propionic acid methyl ester | CC(NP(OC1=CC=CC=C1)(OCC2OC(C)(C)OC2C(NO)=O)=O)C(OC)=O | 1H NMR (500 MHz, CDCl3): δ=1.26–1.30 (6H, m, C(CH3)2), 1.42, 1.44 (3H, 2 s, CHCH3), 3.64, 3.65 (3H, 2 s, OCH3), 3.92–4.22 (4H, m, CHCH3 + CH2OP + OH), 4.49–4.54 (1H, m, CHCH2OP), 4.68 (1H, t, J=7.4 Hz, COCHCH), 7.07–7.10 (1H, m, Ph-H), 7.13–7.16 (2H, m, Ph-H), 7.23–7.26 (2H, m, Ph-H), 8.32 (1H, bs, NH), 8.96 ppm (1H, b... | 13C NMR (125 MHz, CDCl3): δ=20.87, 20.93 (CHCH3), 24.57, 24.59 (C(CH3)2), 26.39, 26.68 (C(CH3)2), 50.0, 50.2 (CHCH3), 52.6 (OCH3), 64.9, 65.4 (CH2OP), 74.8, 75.4 (CHCH2OP), 75.79, 75.87, 75.96, 76.05 (COCHCH), 109.7 (C(CH3)2), 120.2, 120.3 (Ph-CH), 124.9, 125.0 (Ph-CH), 129.7 (Ph-CH), 149.5 (Ph-C), 165.1 ppm (HNCOCH), ... | 500 MHz, CDCl3 | 1.26–1.30 (6H, m, C(CH3)2), 1.42, 1.44 (3H, 2 s, CHCH3), 3.64, 3.65 (3H, 2 s, OCH3), 3.92–4.22 (4H, m, CHCH3 + CH2OP + OH), 4.49–4.54 (1H, m, CHCH2OP), 4.68 (1H, t, J=7.4 Hz, COCHCH), 7.07–7.10 (1H, m, Ph-H), 7.13–7.16 (2H, m, Ph-H), 7.23–7.26 (2H, m, Ph-H), 8.32 (1H, bs, NH), 8.96 ppm (1H, bs, NH) | 125 MHz, CDCl3 | 20.87, 20.93, 24.57, 24.59, 26.39, 26.68, 50.0, 50.2, 52.6, 64.9, 65.4, 74.8, 75.4, 75.79, 75.87, 75.96, 76.05, 109.7, 120.2, 120.3, 124.9, 125.0, 129.7, 149.5, 165.1, 173.8 | 0.424432 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2-[[5-(2,4-Dimethoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-(4-nitro-phenoxy)-phosphorylamino]-propionic acid methyl ester (25c). NMI (0.210 mL, 2.64 mmol) was added dropwise into a solution of 4b (150 mg, 0.44 mmol), 5d (425 mg, 1.32 mmol) in dry DCM (10 mL) at −78°C under Argon. The reaction was ... | 2-[[5-(2,4-Dimethoxy-benzyloxycarbamoyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-(4-nitro-phenoxy)-phosphorylamino]-propionic acid methyl ester | CC(NP(OC1=CC=C([N+]([O-])=O)C=C1)(OCC2OC(C)(C)OC2C(NOCC3=CC=C(OC)C=C3OC)=O)=O)C(OC)=O | 1H NMR (500 MHz, CDCl3): δ=1.30, 1.32 (6H, 2 s, C(CH3)2), 1.42, 1.46 (3H, 2 s, CHCH3), 3.68 (3H, s, OCH3), 4.04–4.09 (1H, m, CHCH3), 4.15–4.23 (2H, m, CH2OP), 4.53 (1H, bs, CHCH2OP), 4.70 (1H, d, J=7.5 Hz, COCHCH), 6.42 (2H, m, Ar-CH2), 7.31 (2H, m, Ar-H), 8.16 (2H, m, Ar-H), 8.93 ppm (1H, bs, NH) | 13C NMR (125 MHz, CDCl3): δ=20.0 (CHCH3), 24.25 (C(CH3)2), 26.67 (C(CH3)2), 50.0, 50.2 (CHCH3), 53.5 (OCH3), 65.1, 65.2 (CH2OP), 75.5, 75.6 (CHCH2OP), 77.6 (COCHCH), 110.5 (C(CH3)2), 120.8, 120.9 (Ph-CH), 125.6, (Ph-CH), 130.7 (Ph-C-NO2), 142.6 (Ph-C), 166.0 (HNCOCH), 173.8 ppm (CO2CH3) | 500 MHz, CDCl3 | 1.30, 1.32 (6H, 2 s, C(CH3)2), 1.42, 1.46 (3H, 2 s, CHCH3), 3.68 (3H, s, OCH3), 4.04–4.09 (1H, m, CHCH3), 4.15–4.23 (2H, m, CH2OP), 4.53 (1H, bs, CHCH2OP), 4.70 (1H, d, J=7.5 Hz, COCHCH), 6.42 (2H, m, Ar-CH2), 7.31 (2H, m, Ar-H), 8.16 (2H, m, Ar-H), 8.93 ppm (1H, bs, NH) | 125 MHz, CDCl3 | 20.0, 24.25, 26.67, 50.0, 50.2, 53.5, 65.1, 65.2, 75.5, 75.6, 77.6, 110.5, 120.8, 120.9, 125.6, 130.7, 142.6, 166.0, 173.8 | 0.246721 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2-Chloro-4H-benzo[1,3,2]dioxaphosphinine (6b). A solution of triethylamine (11.8 mL, 84.6 mmol) in dry ether (70 mL) was added dropwise over 1.5 h into a solution of PCl3 (6.2 mL, 44.3 mmol) and 2-hydroxy benzyl alcohol (5 g, 40.3 mmol) in dry ether (100 mL) at −78°C. The white suspension was vigorously stirred at room... | 2-Chloro-4H-benzo[1,3,2]dioxaphosphinine | ClP1OC2=CC=CC=C2CO1 | 1H NMR (500 MHz, CDCl3): δ=5.07 (1H, dd, J1=14.2, J2=9.6 Hz, Ar-CHHO), 5.49 (1H, dd, J1=14.4, J2=1.9 Hz, Ar-CHHO), 7.01–7.03 (2H, m, Ar-H), 7.15 (1H, t, J=7.5 Hz, Ar-H), 7.31 ppm (1H, t, J=7.5 Hz, Ar-H) | 13C NMR (125 MHz, CDCl3): δ=61.13, 61.14 (ArCH2O), 119.47, 119.49 (Ar-CH), 121.44, 121.54 (Ar-C), 124.04 (Ar-CH), 125.84 (Ar-CH), 129.30 (Ar-CH), 146.13, 146.17 (Ar-C) | 500 MHz, CDCl3 | 5.07 (1H, dd, J1=14.2, J2=9.6 Hz, Ar-CHHO), 5.49 (1H, dd, J1=14.4, J2=1.9 Hz, Ar-CHHO), 7.01–7.03 (2H, m, Ar-H), 7.15 (1H, t, J=7.5 Hz, Ar-H), 7.31 ppm (1H, t, J=7.5 Hz, Ar-H) | 125 MHz, CDCl3 | 61.13, 61.14, 119.47, 119.49, 121.44, 121.54, 124.04, 125.84, 129.30, 146.13, 146.17 | 0.727531 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | 2,2-Dimethyl-5-(2-oxo-2,3-dihydro-2,5-benzo[1,4,2]dioxaphosphinin-2-yloxymethyl)-[1,3]dioxolane-4-carboxylic acid (2,4-dimethoxy-benzyloxy)-amide (28). 6b (166 mg, 0.88 mmol) was added over 5 min to a solution of 4b (150 mg, 0.44 mmol) and DIPEA (0.152 mL, 0.88 mmol) in dry CH3CN (10 mL) cooled with an ice bath. The re... | 2,2-Dimethyl-5-(2-oxo-2,3-dihydro-2,5-benzo[1,4,2]dioxaphosphinin-2-yloxymethyl)-[1,3]dioxolane-4-carboxylic acid (2,4-dimethoxy-benzyloxy)-amide | null | 1H NMR (500 MHz, CDCl3): δ=1.27 (3H, s, C(CH3)2), 1.38, 1.41 (3H, 2 s, C(CH3)2), 3.75 (6H, 2 s, OCH3), 4.04–4.16 (1H, m, CHCHHOP), 4.46–4.57 (3H, m, COCHCHCHHOP), 4.75 (1H, AB syst., J1=11.0, J2=28.4 Hz, ArCHHO), 4.80 (1H, AB syst., J1=11.0, J2=32.9 Hz, ArCHHO), 5.16–5.27 (1H, m, POCHHAr), 5.33–5.39 (1H, m, POCHHAr), 6... | 13C NMR (125 MHz, CDCl3): δ=24.55, 24.58 (C(CH3)2), 26.66, 26.73 (C(CH3)2), 55.44, 55.55, 55.58 (OCH3), 66.60, 66.66, 66.70 (CHCH2OP), 68.54, 68.60, 68.72 (POCH2Ar), 73.53, 73.57 (ArCH2O), 74.90, 75.02 (CHCH2OP), 75.81, 75.87 (COCH), 98.55, 98.57 (Ar-CH), 104.16, 104.19 (Ar-CH), 110.75 (C(CH3)2), 115.63 (Ar-CH), 118.61... | 500 MHz, CDCl3 | 1.27 (3H, s, C(CH3)2), 1.38, 1.41 (3H, 2 s, C(CH3)2), 3.75 (6H, 2 s, OCH3), 4.04–4.16 (1H, m, CHCHHOP), 4.46–4.57 (3H, m, COCHCHCHHOP), 4.75 (1H, AB syst., J1=11.0, J2=28.4 Hz, ArCHHO), 4.80 (1H, AB syst., J1=11.0, J2=32.9 Hz, ArCHHO), 5.16–5.27 (1H, m, POCHHAr), 5.33–5.39 (1H, m, POCHHAr), 6.38–6.42 (2H, m, Ar-H), 6.9... | 125 MHz, CDCl3 | 24.55, 24.58, 26.66, 26.73, 55.44, 55.55, 55.58, 66.60, 66.66, 66.70, 68.54, 68.60, 68.72, 73.53, 73.57, 74.90, 75.02, 75.81, 75.87, 98.55, 98.57, 104.16, 104.19, 110.75, 115.63, 118.61, 118.68, 118.77, 118.84, 120.66, 124.13, 124.18, 125.23, 125.33, 129.60, 129.70, 132.80, 132.88, 150.20, 159.39, 159.43, 161.83, 161.8... | 0.667728 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | Cyclo(saligenyl)-(5-(hydroxycarbamoyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl phosphate ester (3f). Compound 28 (79 mg, 0.155 mmol) was stirred in a solution of TFA 2% in DCM (2 mL). The reaction was monitored by TLC (5% MeOH/DCM). The solution was concentrated under reduced pressure, suspended in MeOH (2 mL), and filtr... | Cyclo(saligenyl)-(5-(hydroxycarbamoyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl phosphate ester | null | 1H NMR (500 MHz, CDCl3): δ=1.38 (3H, s, C(CH3)2), 1.52, 1.55 (3H, 2 s, C(CH3)2), 4.41–4.46 (2H, m, CHCH2OP), 4.60–4.64 (1H, m, CHCH2OP), 4.76–4.78 (1H, m, COCH), 5.31–5.46 (2H, m, OCH2Ar), 7.09–7.11 (2H m, Ar-H), 7.17 (1H, t, J=7.5 Hz, Ar-H), 7.35 (1H, t, J=7.6 Hz, Ar-H), 8.93–9.02 ppm (1H, bs, NH) | 13C NMR (125 MHz, CDCl3): δ=24.45, 24.58 (C(CH3)2), 26.47, 26.63 (C(CH3)2), 66.67, 66.72, 66.77 (CHCH2OP), 68.83, 68.88, 68.94 (POCH2Ar), 74.45, 74.67 (CHCH2OP), 75.66, 75.72 (COCHCH), 110.87, 110.95 (C(CH3)2), 118.66, 118.73, 118.75, 118.83 (Ar-CH), 120.57, 120.65, 120.72 (Ar-C), 124.40 (Ar-CH), 125.33, 125.41 (Ar-CH)... | 500 MHz, CDCl3 | 1.38 (3H, s, C(CH3)2), 1.52, 1.55 (3H, 2 s, C(CH3)2), 4.41–4.46 (2H, m, CHCH2OP), 4.60–4.64 (1H, m, CHCH2OP), 4.76–4.78 (1H, m, COCH), 5.31–5.46 (2H, m, OCH2Ar), 7.09–7.11 (2H m, Ar-H), 7.17 (1H, t, J=7.5 Hz, Ar-H), 7.35 (1H, t, J=7.6 Hz, Ar-H), 8.93–9.02 ppm (1H, bs, NH) | 125 MHz, CDCl3 | 24.45, 24.58, 26.47, 26.63, 66.67, 66.72, 66.77, 68.83, 68.88, 68.94, 74.45, 74.67, 75.66, 75.72, 110.87, 110.95, 118.66, 118.73, 118.75, 118.83, 120.57, 120.65, 120.72, 124.40, 125.33, 125.41, 129.75, 129.78, 149.92, 149.94, 149.97, 150.0, 165.7, 166.0 | 0.75146 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
PMC2248282 | Tris((pivaloyloxy)methyl) phosphate (18). Chloromethyl pivalate (6.05 mL, 41.7 mmol) and NaI (4.84 g, 32.1 mmol) were added into a solution of trimethyl phosphate (1.24 mL, 10.7 mmol) in CH3CN (9 mL). The solution was refluxed (80°C) for 3 days, cooled to room temperature and diluted with diethyl ether (100 mL). The or... | Tris((pivaloyloxy)methyl) phosphate | O=P(OCOC(C(C)(C)C)=O)(OCOC(C(C)(C)C)=O)OCOC(C(C)(C)C)=O | 1H NMR (500 MHz, CDCl3): δ=1.25 (27H, d, J=1.53 Hz, 3×C(CH3)3), 5.68 ppm (6H, dd, J=1.4, 13.8 Hz, 3×OCH2O) | 13C NMR (125 MHz, CDCl3): δ=26.8 (C(CH3)3), 38.8 (C(CH3)3), 82.77 (d, J=5.2 Hz, OCH2O), 176.6 ppm (COC(CH3)3) | 500 MHz, CDCl3 | 1.25 (27H, d, J=1.53 Hz, 3×C(CH3)3), 5.68 ppm (6H, dd, J=1.4, 13.8 Hz, 3×OCH2O) | 125 MHz, CDCl3 | 26.8, 38.8, 82.77, 176.6 | 0.903314 | 17,615,587 | ChemMedChem. 2007 Aug 13; 2(8):1169-1180 | ChemMedChem | 2,007 | CC BY | 2021-01-04 20:13:23 | no |
End of preview.
1. NMRBank data (225809)
We batch processed 380,220 NMR segments using NMRExtractor. After removing entries with empty 13C NMR chemical shifts, we obtained about 260,000 entries. Further filtering out entries with empty IUPAC names and NMR chemical shifts resulted in 225,809 entries.
NMRBank_data_225809.zip
2. NMRBank data with SMILES (156621)
To normalize these data, we converted IUPAC names to SMILES using ChemDraw and OPSIN, successfully converting 156,621 entries. We then normalized SMILES using RDKit.
NMRBank_data_with_SMILES_156621_in_225809.zip
We have normalized the dataset based on standardized SMILES strings. The total number of unique SMILES strings is 149,135.
NMRBank_data_with_unique_SMILES_149135_in_156621.zip
For the highest confidence interval (0.6–1), the number of unique SMILES records is 123,174.
NMRBank_data_with_unique_SMILES_and_confidence_greater_than_0.6_123174_in_149135.zip
For the highest confidence interval (0.8–1), the number of unique SMILES records is 91,707.
NMRBank_data_with_unique_SMILES_and_confidence_greater_than_0.8_91707_in_149135.zip
3. NMRBank dataset in json format
We also provide the NMRBank dataset in JSON format for convenient access and easy viewing.
NMRBank_json_format\NMRBank_data_225809_json_format.zipNMRBank_json_format\NMRBank_json_format\NMRBank_data_with_SMILES_156621_in_225809_json_format.zipNMRBank_json_format\NMRBank_data_with_unique_SMILES_149135_in_156621_json_format.zipNMRBank_json_format\NMRBank_data_with_unique_SMILES_and_confidence_greater_than_0.6_123174_in_149135_json_format.zipNMRBank_json_format\NMRBank_data_with_unique_SMILES_and_confidence_greater_than_0.8_91707_in_149135_json_format.zip
4. NMRBank dataset reading and viewing
Read csv file
import pandas as pd
# Reading csv Files
df = pd.read_csv(r"NMRBank_data_225809.csv", encoding="utf-8")
df
Read json file
import pandas as pd
# Reading json Files
df = pd.read_json(r"NMRBank_data_225809.json", orient="records", lines=True)
df
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