PMC:7291971 / 81149-82394 JSONTXT

{"project":"LitCovid-PMC-OGER-BB","denotations":[{"id":"T1619","span":{"begin":50,"end":65},"obj":"CHEBI:50488;CHEBI:50488"},{"id":"T1620","span":{"begin":66,"end":67},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1621","span":{"begin":68,"end":71},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1622","span":{"begin":71,"end":77},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T1623","span":{"begin":108,"end":118},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T1624","span":{"begin":120,"end":122},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T1625","span":{"begin":122,"end":129},"obj":"CHEBI:43176;CHEBI:43176"},{"id":"T1626","span":{"begin":130,"end":131},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T1627","span":{"begin":133,"end":146},"obj":"CHEBI:24712;CHEBI:24712"},{"id":"T1628","span":{"begin":147,"end":153},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T1629","span":{"begin":153,"end":154},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1630","span":{"begin":154,"end":155},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1631","span":{"begin":155,"end":158},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1632","span":{"begin":158,"end":159},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1633","span":{"begin":159,"end":162},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1634","span":{"begin":172,"end":185},"obj":"CHEBI:23132;CHEBI:23132"},{"id":"T1635","span":{"begin":185,"end":186},"obj":"CHEBI:34674;CHEBI:34674"},{"id":"T1636","span":{"begin":186,"end":188},"obj":"CHEBI:28714;CHEBI:28714"},{"id":"T1637","span":{"begin":188,"end":199},"obj":"CHEBI:35358;CHEBI:35358"},{"id":"T1638","span":{"begin":288,"end":300},"obj":"CHEBI:38472;CHEBI:38472"},{"id":"T1639","span":{"begin":970,"end":973},"obj":"CHEBI:36927;CHEBI:36927"},{"id":"T17925","span":{"begin":50,"end":65},"obj":"CHEBI:50488;CHEBI:50488"},{"id":"T82388","span":{"begin":66,"end":67},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T10723","span":{"begin":68,"end":71},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T18753","span":{"begin":71,"end":77},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T64138","span":{"begin":108,"end":118},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T73883","span":{"begin":120,"end":122},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T72492","span":{"begin":122,"end":129},"obj":"CHEBI:43176;CHEBI:43176"},{"id":"T63934","span":{"begin":130,"end":131},"obj":"CHEBI:34018;CHEBI:34018"},{"id":"T56249","span":{"begin":133,"end":146},"obj":"CHEBI:24712;CHEBI:24712"},{"id":"T30756","span":{"begin":147,"end":153},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T28674","span":{"begin":153,"end":154},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T56815","span":{"begin":154,"end":155},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T26876","span":{"begin":155,"end":158},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T17690","span":{"begin":158,"end":159},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T8379","span":{"begin":159,"end":162},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T16867","span":{"begin":172,"end":185},"obj":"CHEBI:23132;CHEBI:23132"},{"id":"T31770","span":{"begin":185,"end":186},"obj":"CHEBI:34674;CHEBI:34674"},{"id":"T99552","span":{"begin":186,"end":188},"obj":"CHEBI:28714;CHEBI:28714"},{"id":"T7605","span":{"begin":188,"end":199},"obj":"CHEBI:35358;CHEBI:35358"},{"id":"T88840","span":{"begin":288,"end":300},"obj":"CHEBI:38472;CHEBI:38472"},{"id":"T96112","span":{"begin":970,"end":973},"obj":"CHEBI:36927;CHEBI:36927"}],"text":"4.1.37 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-chlorobenzene-1-sulfonamide (14)\nUsing method C with 34 (150 mg, 0.15 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 14 (55 mg, 48%) was obtained as a white powder with 96% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.33 (s, 1H), 8.32 (s, 1H), 8.150 (s, 1H), 8.147 (s, 1H), 7.75–7.68 (m, 2H), 7.53–7.49 (m, 2H), 7.35 (br. s, 2H), 7.28 (br. s, 2H), 5.95 (d, J = 5.5 Hz, 1H), 5.84 (d, J = 5.9 Hz, 1H), 5.52 (d, J = 6.1 Hz, 1H), 5.36 (m, 2H), 5.20 (d, J = 5.2 Hz, 1H), 4.74 (q, J = 5.6 Hz, 1H), 4.39 (t, J = 5.2 Hz, 1H), 4.29 (q, J = 4.7 Hz, 1H), 4.16 (q, J = 4.6 Hz, 1H), 4.11–4.05 (m, 1H), 3.93 (q, J = 3.6 Hz, 1H), 3.73–3.64 (m, 3H), 3.56–3.46 (m, 2H), 3.37–3.29 (m, 3H), 3.22 (dt, J = 14.7 Hz, 6.4 Hz, 1H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5, 152.5, 149.3, 148.9, 140.1, 139.5, 138.0, 137.7, 129.2, 128.7, 119.3, 119.3, 87.7, 86.2, 85.9, 82.1, 81.4, 72.2, 71.3, 69.9, 68.3, 61.1, 50.8, 47.7. HRMS (ESI+): m/z calcd for C28H33N11O9SCl [M+H]+: 734.1868, Found 734.1866."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1523","span":{"begin":288,"end":300},"obj":"Chemical"},{"id":"1524","span":{"begin":304,"end":309},"obj":"Chemical"},{"id":"1525","span":{"begin":449,"end":451},"obj":"Chemical"},{"id":"1526","span":{"begin":466,"end":472},"obj":"Chemical"},{"id":"1527","span":{"begin":487,"end":489},"obj":"Chemical"},{"id":"1528","span":{"begin":501,"end":503},"obj":"Chemical"},{"id":"1529","span":{"begin":516,"end":518},"obj":"Chemical"},{"id":"1530","span":{"begin":531,"end":533},"obj":"Chemical"},{"id":"1531","span":{"begin":550,"end":552},"obj":"Chemical"},{"id":"1532","span":{"begin":569,"end":571},"obj":"Chemical"},{"id":"1533","span":{"begin":587,"end":589},"obj":"Chemical"},{"id":"1534","span":{"begin":970,"end":973},"obj":"Chemical"},{"id":"1535","span":{"begin":988,"end":996},"obj":"Chemical"},{"id":"1536","span":{"begin":1197,"end":1211},"obj":"Chemical"},{"id":"1537","span":{"begin":1170,"end":1174},"obj":"Disease"}],"attributes":[{"id":"A1523","pred":"tao:has_database_id","subj":"1523","obj":"MESH:C032159"},{"id":"A1531","pred":"tao:has_database_id","subj":"1531","obj":"MESH:D003903"},{"id":"A1532","pred":"tao:has_database_id","subj":"1532","obj":"MESH:D003903"},{"id":"A1533","pred":"tao:has_database_id","subj":"1533","obj":"MESH:D003903"},{"id":"A1534","pred":"tao:has_database_id","subj":"1534","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":"4.1.37 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-chlorobenzene-1-sulfonamide (14)\nUsing method C with 34 (150 mg, 0.15 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 14 (55 mg, 48%) was obtained as a white powder with 96% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.33 (s, 1H), 8.32 (s, 1H), 8.150 (s, 1H), 8.147 (s, 1H), 7.75–7.68 (m, 2H), 7.53–7.49 (m, 2H), 7.35 (br. s, 2H), 7.28 (br. s, 2H), 5.95 (d, J = 5.5 Hz, 1H), 5.84 (d, J = 5.9 Hz, 1H), 5.52 (d, J = 6.1 Hz, 1H), 5.36 (m, 2H), 5.20 (d, J = 5.2 Hz, 1H), 4.74 (q, J = 5.6 Hz, 1H), 4.39 (t, J = 5.2 Hz, 1H), 4.29 (q, J = 4.7 Hz, 1H), 4.16 (q, J = 4.6 Hz, 1H), 4.11–4.05 (m, 1H), 3.93 (q, J = 3.6 Hz, 1H), 3.73–3.64 (m, 3H), 3.56–3.46 (m, 2H), 3.37–3.29 (m, 3H), 3.22 (dt, J = 14.7 Hz, 6.4 Hz, 1H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5, 152.5, 149.3, 148.9, 140.1, 139.5, 138.0, 137.7, 129.2, 128.7, 119.3, 119.3, 87.7, 86.2, 85.9, 82.1, 81.4, 72.2, 71.3, 69.9, 68.3, 61.1, 50.8, 47.7. HRMS (ESI+): m/z calcd for C28H33N11O9SCl [M+H]+: 734.1868, Found 734.1866."}

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T428","span":{"begin":225,"end":227},"obj":"http://purl.obolibrary.org/obo/CLO_0001302"},{"id":"T429","span":{"begin":261,"end":262},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T430","span":{"begin":358,"end":360},"obj":"http://purl.obolibrary.org/obo/CLO_0001382"},{"id":"T431","span":{"begin":379,"end":380},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T432","span":{"begin":1213,"end":1216},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"4.1.37 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-chlorobenzene-1-sulfonamide (14)\nUsing method C with 34 (150 mg, 0.15 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 14 (55 mg, 48%) was obtained as a white powder with 96% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.33 (s, 1H), 8.32 (s, 1H), 8.150 (s, 1H), 8.147 (s, 1H), 7.75–7.68 (m, 2H), 7.53–7.49 (m, 2H), 7.35 (br. s, 2H), 7.28 (br. s, 2H), 5.95 (d, J = 5.5 Hz, 1H), 5.84 (d, J = 5.9 Hz, 1H), 5.52 (d, J = 6.1 Hz, 1H), 5.36 (m, 2H), 5.20 (d, J = 5.2 Hz, 1H), 4.74 (q, J = 5.6 Hz, 1H), 4.39 (t, J = 5.2 Hz, 1H), 4.29 (q, J = 4.7 Hz, 1H), 4.16 (q, J = 4.6 Hz, 1H), 4.11–4.05 (m, 1H), 3.93 (q, J = 3.6 Hz, 1H), 3.73–3.64 (m, 3H), 3.56–3.46 (m, 2H), 3.37–3.29 (m, 3H), 3.22 (dt, J = 14.7 Hz, 6.4 Hz, 1H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5, 152.5, 149.3, 148.9, 140.1, 139.5, 138.0, 137.7, 129.2, 128.7, 119.3, 119.3, 87.7, 86.2, 85.9, 82.1, 81.4, 72.2, 71.3, 69.9, 68.3, 61.1, 50.8, 47.7. HRMS (ESI+): m/z calcd for C28H33N11O9SCl [M+H]+: 734.1868, Found 734.1866."}

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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-chlorobenzene-1-sulfonamide (14)\nUsing method C with 34 (150 mg, 0.15 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 14 (55 mg, 48%) was obtained as a white powder with 96% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.33 (s, 1H), 8.32 (s, 1H), 8.150 (s, 1H), 8.147 (s, 1H), 7.75–7.68 (m, 2H), 7.53–7.49 (m, 2H), 7.35 (br. s, 2H), 7.28 (br. s, 2H), 5.95 (d, J = 5.5 Hz, 1H), 5.84 (d, J = 5.9 Hz, 1H), 5.52 (d, J = 6.1 Hz, 1H), 5.36 (m, 2H), 5.20 (d, J = 5.2 Hz, 1H), 4.74 (q, J = 5.6 Hz, 1H), 4.39 (t, J = 5.2 Hz, 1H), 4.29 (q, J = 4.7 Hz, 1H), 4.16 (q, J = 4.6 Hz, 1H), 4.11–4.05 (m, 1H), 3.93 (q, J = 3.6 Hz, 1H), 3.73–3.64 (m, 3H), 3.56–3.46 (m, 2H), 3.37–3.29 (m, 3H), 3.22 (dt, J = 14.7 Hz, 6.4 Hz, 1H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5, 152.5, 149.3, 148.9, 140.1, 139.5, 138.0, 137.7, 129.2, 128.7, 119.3, 119.3, 87.7, 86.2, 85.9, 82.1, 81.4, 72.2, 71.3, 69.9, 68.3, 61.1, 50.8, 47.7. HRMS (ESI+): m/z calcd for C28H33N11O9SCl [M+H]+: 734.1868, Found 734.1866."}

{"project":"LitCovid-sentences","denotations":[{"id":"T540","span":{"begin":0,"end":204},"obj":"Sentence"},{"id":"T541","span":{"begin":205,"end":448},"obj":"Sentence"},{"id":"T542","span":{"begin":449,"end":969},"obj":"Sentence"},{"id":"T543","span":{"begin":970,"end":1169},"obj":"Sentence"},{"id":"T544","span":{"begin":1170,"end":1219},"obj":"Sentence"},{"id":"T545","span":{"begin":1220,"end":1245},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"4.1.37 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-chlorobenzene-1-sulfonamide (14)\nUsing method C with 34 (150 mg, 0.15 mmol, 1.00 eq) and a 0–40% linear gradient of acetonitrile in TEAAc buffer 50 mM, pH 7 for purification, 14 (55 mg, 48%) was obtained as a white powder with 96% purity determined by HPLC analysis at 260 nm. 1H NMR (600 MHz, DMSO‑d 6) δ 8.33 (s, 1H), 8.32 (s, 1H), 8.150 (s, 1H), 8.147 (s, 1H), 7.75–7.68 (m, 2H), 7.53–7.49 (m, 2H), 7.35 (br. s, 2H), 7.28 (br. s, 2H), 5.95 (d, J = 5.5 Hz, 1H), 5.84 (d, J = 5.9 Hz, 1H), 5.52 (d, J = 6.1 Hz, 1H), 5.36 (m, 2H), 5.20 (d, J = 5.2 Hz, 1H), 4.74 (q, J = 5.6 Hz, 1H), 4.39 (t, J = 5.2 Hz, 1H), 4.29 (q, J = 4.7 Hz, 1H), 4.16 (q, J = 4.6 Hz, 1H), 4.11–4.05 (m, 1H), 3.93 (q, J = 3.6 Hz, 1H), 3.73–3.64 (m, 3H), 3.56–3.46 (m, 2H), 3.37–3.29 (m, 3H), 3.22 (dt, J = 14.7 Hz, 6.4 Hz, 1H). 13C NMR (150 MHz, DMSO‑d 6) δ 156.1, 156.0, 152.5, 152.5, 149.3, 148.9, 140.1, 139.5, 138.0, 137.7, 129.2, 128.7, 119.3, 119.3, 87.7, 86.2, 85.9, 82.1, 81.4, 72.2, 71.3, 69.9, 68.3, 61.1, 50.8, 47.7. HRMS (ESI+): m/z calcd for C28H33N11O9SCl [M+H]+: 734.1868, Found 734.1866."}