PMC:7291971 / 47113-48711 JSON TXT

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LitCovid-PMC-OGER-BB

LitCovid-PubTator

{"project":"LitCovid-PubTator","denotations":[{"id":"830","span":{"begin":279,"end":282},"obj":"Chemical"},{"id":"831","span":{"begin":296,"end":301},"obj":"Chemical"},{"id":"832","span":{"begin":415,"end":418},"obj":"Chemical"},{"id":"833","span":{"begin":422,"end":426},"obj":"Chemical"},{"id":"834","span":{"begin":572,"end":582},"obj":"Chemical"},{"id":"835","span":{"begin":639,"end":651},"obj":"Chemical"},{"id":"836","span":{"begin":655,"end":660},"obj":"Chemical"},{"id":"837","span":{"begin":771,"end":776},"obj":"Chemical"},{"id":"838","span":{"begin":1336,"end":1339},"obj":"Chemical"},{"id":"839","span":{"begin":1354,"end":1357},"obj":"Chemical"},{"id":"840","span":{"begin":1552,"end":1563},"obj":"Chemical"},{"id":"841","span":{"begin":1525,"end":1529},"obj":"Disease"}],"attributes":[{"id":"A830","pred":"tao:has_database_id","subj":"830","obj":"MESH:D014269"},{"id":"A831","pred":"tao:has_database_id","subj":"831","obj":"MESH:D014867"},{"id":"A834","pred":"tao:has_database_id","subj":"834","obj":"MESH:D058428"},{"id":"A835","pred":"tao:has_database_id","subj":"835","obj":"MESH:C032159"},{"id":"A837","pred":"tao:has_database_id","subj":"837","obj":"MESH:D014867"},{"id":"A838","pred":"tao:has_database_id","subj":"838","obj":"MESH:C000615229"}],"namespaces":[{"prefix":"Tax","uri":"https://www.ncbi.nlm.nih.gov/taxonomy/"},{"prefix":"MESH","uri":"https://id.nlm.nih.gov/mesh/"},{"prefix":"Gene","uri":"https://www.ncbi.nlm.nih.gov/gene/"},{"prefix":"CVCL","uri":"https://web.expasy.org/cellosaurus/CVCL_"}],"text":"4.1.12 (2S)-2-amino-4-({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)amino)butanamide (4)\nCompound 22 (116 mg, 0.10 mmol, 1.00 eq) was treated at room temperature with TFA (1.44 mL) in water (360 μL) and stirred for 3 h at room temperature. The solvents were removed and the residue was treated with 7 M NH3 in MeOH (10 mL). After stirring for 24 h at 30 °C, solvents were removed and the residue was purified by flash column chromatography on a reversed-phase silica gel column C18 (4 g, 40 μm) with a 0–15% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7. The fractions containing the pure compound were pooled, concentrated and lyophilized with water to give 4 (23 mg, 38%) as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, D2O) δ 8.12 (s, 1H), 8.08 (s, 1H), 7.99 (s, 1H), 7.90 (s, 1H), 5.90 (d, J = 2.7 Hz, 1H), 5.79 (d, J = 3.5 Hz, 1H), 4.53 (dd, J = 5.2 Hz, J = 2.7 Hz, 1H), 4.52–4.48 (m, 1H), 4.38 (dd, J = 5.0 Hz, J = 3.6 Hz, 1H), 4.35–4.28 (m, 1H), 4.18–4.07 (m, 3H), 3.98 (td, J = 10.7 Hz, J = 2.6 Hz, 1H), 3.88–3.80 (m, 2H), 3.72 (dd, J = 12.9 Hz, J = 3.5 Hz, 1H), 3.16–2.98 (m, 3H), 2.88–2.76 (m, 2H), 2.62 (dt, J = 14.0 Hz, J = 2.7 Hz, 1H), 2.17–1.98 (m, 2H). 13C NMR (150 MHz, D2O) δ 173.0, 155.0 (2C) 152.5, 152.3, 147.8, 147.6, 139.4, 138.7, 118.6, 118.3, 88.9, 86.8, 84.9, 81.8, 79.8, 73.8, 71.1, 69.0, 67.6, 60.4, 55.3, 53.9, 52.6, 52.4, 27.0. HRMS (ESI+): m/z calcd for C26H38N13O8 [M+H]+: 660.2961, found: 660.2966."}

LitCovid-PD-CLO

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T318","span":{"begin":210,"end":212},"obj":"http://purl.obolibrary.org/obo/CLO_0050507"},{"id":"T319","span":{"begin":214,"end":217},"obj":"http://purl.obolibrary.org/obo/CLO_0001046"},{"id":"T320","span":{"begin":555,"end":556},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T321","span":{"begin":612,"end":613},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T322","span":{"begin":791,"end":797},"obj":"http://purl.obolibrary.org/obo/CLO_0007698"},{"id":"T323","span":{"begin":803,"end":804},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T324","span":{"begin":1565,"end":1568},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"4.1.12 (2S)-2-amino-4-({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)amino)butanamide (4)\nCompound 22 (116 mg, 0.10 mmol, 1.00 eq) was treated at room temperature with TFA (1.44 mL) in water (360 μL) and stirred for 3 h at room temperature. The solvents were removed and the residue was treated with 7 M NH3 in MeOH (10 mL). After stirring for 24 h at 30 °C, solvents were removed and the residue was purified by flash column chromatography on a reversed-phase silica gel column C18 (4 g, 40 μm) with a 0–15% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7. The fractions containing the pure compound were pooled, concentrated and lyophilized with water to give 4 (23 mg, 38%) as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, D2O) δ 8.12 (s, 1H), 8.08 (s, 1H), 7.99 (s, 1H), 7.90 (s, 1H), 5.90 (d, J = 2.7 Hz, 1H), 5.79 (d, J = 3.5 Hz, 1H), 4.53 (dd, J = 5.2 Hz, J = 2.7 Hz, 1H), 4.52–4.48 (m, 1H), 4.38 (dd, J = 5.0 Hz, J = 3.6 Hz, 1H), 4.35–4.28 (m, 1H), 4.18–4.07 (m, 3H), 3.98 (td, J = 10.7 Hz, J = 2.6 Hz, 1H), 3.88–3.80 (m, 2H), 3.72 (dd, J = 12.9 Hz, J = 3.5 Hz, 1H), 3.16–2.98 (m, 3H), 2.88–2.76 (m, 2H), 2.62 (dt, J = 14.0 Hz, J = 2.7 Hz, 1H), 2.17–1.98 (m, 2H). 13C NMR (150 MHz, D2O) δ 173.0, 155.0 (2C) 152.5, 152.3, 147.8, 147.6, 139.4, 138.7, 118.6, 118.3, 88.9, 86.8, 84.9, 81.8, 79.8, 73.8, 71.1, 69.0, 67.6, 60.4, 55.3, 53.9, 52.6, 52.4, 27.0. HRMS (ESI+): m/z calcd for C26H38N13O8 [M+H]+: 660.2961, found: 660.2966."}

LitCovid-PD-CHEBI

LitCovid-sentences

{"project":"LitCovid-sentences","denotations":[{"id":"T342","span":{"begin":0,"end":200},"obj":"Sentence"},{"id":"T343","span":{"begin":201,"end":351},"obj":"Sentence"},{"id":"T344","span":{"begin":352,"end":435},"obj":"Sentence"},{"id":"T345","span":{"begin":436,"end":680},"obj":"Sentence"},{"id":"T346","span":{"begin":681,"end":872},"obj":"Sentence"},{"id":"T347","span":{"begin":873,"end":1335},"obj":"Sentence"},{"id":"T348","span":{"begin":1336,"end":1524},"obj":"Sentence"},{"id":"T349","span":{"begin":1525,"end":1571},"obj":"Sentence"},{"id":"T350","span":{"begin":1572,"end":1588},"obj":"Sentence"},{"id":"T351","span":{"begin":1589,"end":1598},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"4.1.12 (2S)-2-amino-4-({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)amino)butanamide (4)\nCompound 22 (116 mg, 0.10 mmol, 1.00 eq) was treated at room temperature with TFA (1.44 mL) in water (360 μL) and stirred for 3 h at room temperature. The solvents were removed and the residue was treated with 7 M NH3 in MeOH (10 mL). After stirring for 24 h at 30 °C, solvents were removed and the residue was purified by flash column chromatography on a reversed-phase silica gel column C18 (4 g, 40 μm) with a 0–15% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7. The fractions containing the pure compound were pooled, concentrated and lyophilized with water to give 4 (23 mg, 38%) as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, D2O) δ 8.12 (s, 1H), 8.08 (s, 1H), 7.99 (s, 1H), 7.90 (s, 1H), 5.90 (d, J = 2.7 Hz, 1H), 5.79 (d, J = 3.5 Hz, 1H), 4.53 (dd, J = 5.2 Hz, J = 2.7 Hz, 1H), 4.52–4.48 (m, 1H), 4.38 (dd, J = 5.0 Hz, J = 3.6 Hz, 1H), 4.35–4.28 (m, 1H), 4.18–4.07 (m, 3H), 3.98 (td, J = 10.7 Hz, J = 2.6 Hz, 1H), 3.88–3.80 (m, 2H), 3.72 (dd, J = 12.9 Hz, J = 3.5 Hz, 1H), 3.16–2.98 (m, 3H), 2.88–2.76 (m, 2H), 2.62 (dt, J = 14.0 Hz, J = 2.7 Hz, 1H), 2.17–1.98 (m, 2H). 13C NMR (150 MHz, D2O) δ 173.0, 155.0 (2C) 152.5, 152.3, 147.8, 147.6, 139.4, 138.7, 118.6, 118.3, 88.9, 86.8, 84.9, 81.8, 79.8, 73.8, 71.1, 69.0, 67.6, 60.4, 55.3, 53.9, 52.6, 52.4, 27.0. HRMS (ESI+): m/z calcd for C26H38N13O8 [M+H]+: 660.2961, found: 660.2966."}