PMC:7291971 / 73940-75224 JSONTXT

{"project":"LitCovid-PMC-OGER-BB","denotations":[{"id":"T1471","span":{"begin":50,"end":65},"obj":"CHEBI:50488;CHEBI:50488"},{"id":"T1472","span":{"begin":66,"end":67},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1473","span":{"begin":68,"end":71},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1474","span":{"begin":71,"end":77},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T1475","span":{"begin":108,"end":118},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T1476","span":{"begin":120,"end":122},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T1477","span":{"begin":122,"end":129},"obj":"CHEBI:43176;CHEBI:43176"},{"id":"T1478","span":{"begin":130,"end":131},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T1479","span":{"begin":133,"end":146},"obj":"CHEBI:24712;CHEBI:24712"},{"id":"T1480","span":{"begin":147,"end":153},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T1481","span":{"begin":153,"end":154},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1482","span":{"begin":154,"end":155},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1483","span":{"begin":155,"end":158},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1484","span":{"begin":158,"end":159},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1485","span":{"begin":159,"end":162},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1486","span":{"begin":172,"end":178},"obj":"CHEBI:47853;CHEBI:47853"},{"id":"T1487","span":{"begin":178,"end":181},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T1488","span":{"begin":181,"end":193},"obj":"CHEBI:27798;CHEBI:27798"},{"id":"T1489","span":{"begin":193,"end":196},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T1490","span":{"begin":196,"end":207},"obj":"CHEBI:35358;CHEBI:35358"},{"id":"T1491","span":{"begin":296,"end":308},"obj":"CHEBI:38472;CHEBI:38472"},{"id":"T1492","span":{"begin":994,"end":997},"obj":"CHEBI:36927;CHEBI:36927"},{"id":"T40026","span":{"begin":50,"end":65},"obj":"CHEBI:50488;CHEBI:50488"},{"id":"T28765","span":{"begin":66,"end":67},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T9151","span":{"begin":68,"end":71},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T2628","span":{"begin":71,"end":77},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T10304","span":{"begin":108,"end":118},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T30594","span":{"begin":120,"end":122},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T33230","span":{"begin":122,"end":129},"obj":"CHEBI:43176;CHEBI:43176"},{"id":"T38807","span":{"begin":130,"end":131},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T78456","span":{"begin":133,"end":146},"obj":"CHEBI:24712;CHEBI:24712"},{"id":"T45407","span":{"begin":147,"end":153},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T96949","span":{"begin":153,"end":154},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T30771","span":{"begin":154,"end":155},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T52396","span":{"begin":155,"end":158},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T27861","span":{"begin":158,"end":159},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T30803","span":{"begin":159,"end":162},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T29803","span":{"begin":172,"end":178},"obj":"CHEBI:47853;CHEBI:47853"},{"id":"T18253","span":{"begin":178,"end":181},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T10920","span":{"begin":181,"end":193},"obj":"CHEBI:27798;CHEBI:27798"},{"id":"T29304","span":{"begin":193,"end":196},"obj":"CHEBI:86228;CHEBI:86228"},{"id":"T57790","span":{"begin":196,"end":207},"obj":"CHEBI:35358;CHEBI:35358"},{"id":"T31150","span":{"begin":296,"end":308},"obj":"CHEBI:38472;CHEBI:38472"},{"id":"T95477","span":{"begin":994,"end":997},"obj":"CHEBI:36927;CHEBI:36927"}],"text":"4.1.33 N-{[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-N-(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)-4-chloro-3-nitrobenzene-1-sulfonamide (13)\nUsing method C with 33 (121 mg, 0.12 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 13 (14 mg, 16%) was obtained as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (500 MHz, DMSO‑d 6) δ 8.42 (d, J = 2.2 Hz, 1H), 8.34 (s, 1H), 8.32 (s, 1H), 8.144 (s, 1H), 8.140 (s, 1H), 7.96 (dd, J = 8.5 Hz, J = 2.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.41 (br. s, 2H) 7.35 (br. s, 2H), 5.90 (d, J = 5.2 Hz, 1H), 5.83 (d, J = 5.8 Hz, 1H), 5.59 (d, J = 6.0 Hz, 1H), 5.48–5.31 (m, 2H), 5.25 (d, J = 5.3 Hz, 1H), 4.72 (q, J = 5.5 Hz, 1H), 4.36 (t, J = 5.0 Hz, 1H), 4.29 (q, J = 4.6 Hz, 1H), 4.22–4.08 (m, 2H), 3.87 (q, J = 3.6 Hz, 1H), 3.78–3.70 (m, 2H), 3.67 (dd, J = 12.2 Hz, J = 3.4 Hz, 1H), 3.56–3.29 (m, 5H). 13C NMR (125 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.6, 152.5, 149.3, 148.9, 147.4, 140.1, 139.5, 139.5, 132.7, 131.6, 129.6, 124.3, 119.3, 119.3, 87.6, 86.2, 85.8, 81.8, 81.5, 72.3, 71.3, 68.8, 68.1, 61.4, 50.8, 48.1. HRMS (ESI+): m/z calcd for C28H32N12O11SCl [M+H]+: 779.1723, Found 779.1730."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1374","span":{"begin":296,"end":308},"obj":"Chemical"},{"id":"1375","span":{"begin":312,"end":317},"obj":"Chemical"},{"id":"1376","span":{"begin":457,"end":459},"obj":"Chemical"},{"id":"1377","span":{"begin":474,"end":480},"obj":"Chemical"},{"id":"1378","span":{"begin":507,"end":509},"obj":"Chemical"},{"id":"1379","span":{"begin":521,"end":523},"obj":"Chemical"},{"id":"1380","span":{"begin":535,"end":537},"obj":"Chemical"},{"id":"1381","span":{"begin":550,"end":552},"obj":"Chemical"},{"id":"1382","span":{"begin":565,"end":567},"obj":"Chemical"},{"id":"1383","span":{"begin":604,"end":606},"obj":"Chemical"},{"id":"1384","span":{"begin":630,"end":632},"obj":"Chemical"},{"id":"1385","span":{"begin":648,"end":650},"obj":"Chemical"},{"id":"1386","span":{"begin":1235,"end":1250},"obj":"Chemical"},{"id":"1387","span":{"begin":1208,"end":1212},"obj":"Disease"}],"attributes":[{"id":"A1374","pred":"tao:has_database_id","subj":"1374","obj":"MESH:C032159"},{"id":"A1385","pred":"tao:has_database_id","subj":"1385","obj":"MESH:D003903"}],"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":"4.1.33 N-{[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-N-(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)-4-chloro-3-nitrobenzene-1-sulfonamide (13)\nUsing method C with 33 (121 mg, 0.12 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 13 (14 mg, 16%) was obtained as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (500 MHz, DMSO‑d 6) δ 8.42 (d, J = 2.2 Hz, 1H), 8.34 (s, 1H), 8.32 (s, 1H), 8.144 (s, 1H), 8.140 (s, 1H), 7.96 (dd, J = 8.5 Hz, J = 2.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.41 (br. s, 2H) 7.35 (br. s, 2H), 5.90 (d, J = 5.2 Hz, 1H), 5.83 (d, J = 5.8 Hz, 1H), 5.59 (d, J = 6.0 Hz, 1H), 5.48–5.31 (m, 2H), 5.25 (d, J = 5.3 Hz, 1H), 4.72 (q, J = 5.5 Hz, 1H), 4.36 (t, J = 5.0 Hz, 1H), 4.29 (q, J = 4.6 Hz, 1H), 4.22–4.08 (m, 2H), 3.87 (q, J = 3.6 Hz, 1H), 3.78–3.70 (m, 2H), 3.67 (dd, J = 12.2 Hz, J = 3.4 Hz, 1H), 3.56–3.29 (m, 5H). 13C NMR (125 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.6, 152.5, 149.3, 148.9, 147.4, 140.1, 139.5, 139.5, 132.7, 131.6, 129.6, 124.3, 119.3, 119.3, 87.6, 86.2, 85.8, 81.8, 81.5, 72.3, 71.3, 68.8, 68.1, 61.4, 50.8, 48.1. HRMS (ESI+): m/z calcd for C28H32N12O11SCl [M+H]+: 779.1723, Found 779.1730."}

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T400","span":{"begin":237,"end":240},"obj":"http://purl.obolibrary.org/obo/CLO_0001053"},{"id":"T401","span":{"begin":269,"end":270},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T402","span":{"begin":387,"end":388},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T403","span":{"begin":1252,"end":1255},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"4.1.33 N-{[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-N-(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)-4-chloro-3-nitrobenzene-1-sulfonamide (13)\nUsing method C with 33 (121 mg, 0.12 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 13 (14 mg, 16%) was obtained as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (500 MHz, DMSO‑d 6) δ 8.42 (d, J = 2.2 Hz, 1H), 8.34 (s, 1H), 8.32 (s, 1H), 8.144 (s, 1H), 8.140 (s, 1H), 7.96 (dd, J = 8.5 Hz, J = 2.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.41 (br. s, 2H) 7.35 (br. s, 2H), 5.90 (d, J = 5.2 Hz, 1H), 5.83 (d, J = 5.8 Hz, 1H), 5.59 (d, J = 6.0 Hz, 1H), 5.48–5.31 (m, 2H), 5.25 (d, J = 5.3 Hz, 1H), 4.72 (q, J = 5.5 Hz, 1H), 4.36 (t, J = 5.0 Hz, 1H), 4.29 (q, J = 4.6 Hz, 1H), 4.22–4.08 (m, 2H), 3.87 (q, J = 3.6 Hz, 1H), 3.78–3.70 (m, 2H), 3.67 (dd, J = 12.2 Hz, J = 3.4 Hz, 1H), 3.56–3.29 (m, 5H). 13C NMR (125 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.6, 152.5, 149.3, 148.9, 147.4, 140.1, 139.5, 139.5, 132.7, 131.6, 129.6, 124.3, 119.3, 119.3, 87.6, 86.2, 85.8, 81.8, 81.5, 72.3, 71.3, 68.8, 68.1, 61.4, 50.8, 48.1. HRMS (ESI+): m/z calcd for C28H32N12O11SCl [M+H]+: 779.1723, Found 779.1730."}

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","subj":"T77813","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A85935","pred":"chebi_id","subj":"T77672","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A36366","pred":"chebi_id","subj":"T56894","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A50956","pred":"chebi_id","subj":"T4703","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A63877","pred":"chebi_id","subj":"T20231","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A50254","pred":"chebi_id","subj":"T2314","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A56480","pred":"chebi_id","subj":"T51379","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"}],"text":"4.1.33 N-{[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-N-(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)-4-chloro-3-nitrobenzene-1-sulfonamide (13)\nUsing method C with 33 (121 mg, 0.12 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 13 (14 mg, 16%) was obtained as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (500 MHz, DMSO‑d 6) δ 8.42 (d, J = 2.2 Hz, 1H), 8.34 (s, 1H), 8.32 (s, 1H), 8.144 (s, 1H), 8.140 (s, 1H), 7.96 (dd, J = 8.5 Hz, J = 2.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.41 (br. s, 2H) 7.35 (br. s, 2H), 5.90 (d, J = 5.2 Hz, 1H), 5.83 (d, J = 5.8 Hz, 1H), 5.59 (d, J = 6.0 Hz, 1H), 5.48–5.31 (m, 2H), 5.25 (d, J = 5.3 Hz, 1H), 4.72 (q, J = 5.5 Hz, 1H), 4.36 (t, J = 5.0 Hz, 1H), 4.29 (q, J = 4.6 Hz, 1H), 4.22–4.08 (m, 2H), 3.87 (q, J = 3.6 Hz, 1H), 3.78–3.70 (m, 2H), 3.67 (dd, J = 12.2 Hz, J = 3.4 Hz, 1H), 3.56–3.29 (m, 5H). 13C NMR (125 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.6, 152.5, 149.3, 148.9, 147.4, 140.1, 139.5, 139.5, 132.7, 131.6, 129.6, 124.3, 119.3, 119.3, 87.6, 86.2, 85.8, 81.8, 81.5, 72.3, 71.3, 68.8, 68.1, 61.4, 50.8, 48.1. HRMS (ESI+): m/z calcd for C28H32N12O11SCl [M+H]+: 779.1723, Found 779.1730."}

{"project":"LitCovid-sentences","denotations":[{"id":"T498","span":{"begin":0,"end":212},"obj":"Sentence"},{"id":"T499","span":{"begin":213,"end":456},"obj":"Sentence"},{"id":"T500","span":{"begin":457,"end":993},"obj":"Sentence"},{"id":"T501","span":{"begin":994,"end":1207},"obj":"Sentence"},{"id":"T502","span":{"begin":1208,"end":1258},"obj":"Sentence"},{"id":"T503","span":{"begin":1259,"end":1284},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"4.1.33 N-{[(2R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-N-(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}ethyl)-4-chloro-3-nitrobenzene-1-sulfonamide (13)\nUsing method C with 33 (121 mg, 0.12 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 13 (14 mg, 16%) was obtained as a white powder with 98% purity determined by HPLC analysis at 260 nm. 1H NMR (500 MHz, DMSO‑d 6) δ 8.42 (d, J = 2.2 Hz, 1H), 8.34 (s, 1H), 8.32 (s, 1H), 8.144 (s, 1H), 8.140 (s, 1H), 7.96 (dd, J = 8.5 Hz, J = 2.2 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.41 (br. s, 2H) 7.35 (br. s, 2H), 5.90 (d, J = 5.2 Hz, 1H), 5.83 (d, J = 5.8 Hz, 1H), 5.59 (d, J = 6.0 Hz, 1H), 5.48–5.31 (m, 2H), 5.25 (d, J = 5.3 Hz, 1H), 4.72 (q, J = 5.5 Hz, 1H), 4.36 (t, J = 5.0 Hz, 1H), 4.29 (q, J = 4.6 Hz, 1H), 4.22–4.08 (m, 2H), 3.87 (q, J = 3.6 Hz, 1H), 3.78–3.70 (m, 2H), 3.67 (dd, J = 12.2 Hz, J = 3.4 Hz, 1H), 3.56–3.29 (m, 5H). 13C NMR (125 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.6, 152.5, 149.3, 148.9, 147.4, 140.1, 139.5, 139.5, 132.7, 131.6, 129.6, 124.3, 119.3, 119.3, 87.6, 86.2, 85.8, 81.8, 81.5, 72.3, 71.3, 68.8, 68.1, 61.4, 50.8, 48.1. HRMS (ESI+): m/z calcd for C28H32N12O11SCl [M+H]+: 779.1723, Found 779.1730."}