PMC:7571312 / 76301-77563 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T574","span":{"begin":152,"end":154},"obj":"http://purl.obolibrary.org/obo/CLO_0001302"},{"id":"T575","span":{"begin":550,"end":551},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T576","span":{"begin":1046,"end":1048},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T577","span":{"begin":1081,"end":1086},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"N-((1S)-1-{[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide (34)\nFollowing the procedure described for the preparation of N-[(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide but substituting N1-((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-4-methyl-l-leucinamide and making noncritical variations provided a golden syrup. This material was purified by Biotage MPLC (25 M column, 3% methanol/chloroform) to afford 173 mg (60%) of the title compound as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.43 (app t, J = 8 Hz, 2H), 7.62 (s, 1H), 7.32 (m, 6H), 7.08 (t, J = 8 Hz, 1H), 7.00 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.52 (m, 1H), 4.47–4.35 (m, 4H), 4.22 (d, J = 16 Hz, 1H), 3.87 (s, 3H), 3.05 (m, 2H), 2.28 (m, 1H), 2.06 (m, 1H), 1.93 (m, 1H), 1.64–1.57 (m, 3H), 0.92 (s, 9H); MS (ESI+) for C32H40N4O6m/z 577.2 (M + H)+; anal. calcd for C32H40N4O6·0.33 methanol·0.25 H2O: C, 65.62; H, 7.13; N, 9.47. Found: C, 65.65; H, 6.90; N, 9.58; HRMS (ESI+) calcd for C32H40N4O6 577.3021, found 577.3001."}

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(34)\nFollowing the procedure described for the preparation of N-[(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide but substituting N1-((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-4-methyl-l-leucinamide and making noncritical variations provided a golden syrup. This material was purified by Biotage MPLC (25 M column, 3% methanol/chloroform) to afford 173 mg (60%) of the title compound as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.43 (app t, J = 8 Hz, 2H), 7.62 (s, 1H), 7.32 (m, 6H), 7.08 (t, J = 8 Hz, 1H), 7.00 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.52 (m, 1H), 4.47–4.35 (m, 4H), 4.22 (d, J = 16 Hz, 1H), 3.87 (s, 3H), 3.05 (m, 2H), 2.28 (m, 1H), 2.06 (m, 1H), 1.93 (m, 1H), 1.64–1.57 (m, 3H), 0.92 (s, 9H); MS (ESI+) for C32H40N4O6m/z 577.2 (M + H)+; anal. calcd for C32H40N4O6·0.33 methanol·0.25 H2O: C, 65.62; H, 7.13; N, 9.47. Found: C, 65.65; H, 6.90; N, 9.58; HRMS (ESI+) calcd for C32H40N4O6 577.3021, found 577.3001."}

{"project":"LitCovid-sentences","denotations":[{"id":"T464","span":{"begin":0,"end":155},"obj":"Sentence"},{"id":"T465","span":{"begin":156,"end":565},"obj":"Sentence"},{"id":"T466","span":{"begin":566,"end":713},"obj":"Sentence"},{"id":"T467","span":{"begin":714,"end":1168},"obj":"Sentence"},{"id":"T468","span":{"begin":1169,"end":1262},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"N-((1S)-1-{[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide (34)\nFollowing the procedure described for the preparation of N-[(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide but substituting N1-((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-4-methyl-l-leucinamide and making noncritical variations provided a golden syrup. This material was purified by Biotage MPLC (25 M column, 3% methanol/chloroform) to afford 173 mg (60%) of the title compound as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.43 (app t, J = 8 Hz, 2H), 7.62 (s, 1H), 7.32 (m, 6H), 7.08 (t, J = 8 Hz, 1H), 7.00 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.52 (m, 1H), 4.47–4.35 (m, 4H), 4.22 (d, J = 16 Hz, 1H), 3.87 (s, 3H), 3.05 (m, 2H), 2.28 (m, 1H), 2.06 (m, 1H), 1.93 (m, 1H), 1.64–1.57 (m, 3H), 0.92 (s, 9H); MS (ESI+) for C32H40N4O6m/z 577.2 (M + H)+; anal. calcd for C32H40N4O6·0.33 methanol·0.25 H2O: C, 65.62; H, 7.13; N, 9.47. Found: C, 65.65; H, 6.90; N, 9.58; HRMS (ESI+) calcd for C32H40N4O6 577.3021, found 577.3001."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1623","span":{"begin":626,"end":634},"obj":"Chemical"},{"id":"1624","span":{"begin":635,"end":645},"obj":"Chemical"},{"id":"1625","span":{"begin":1106,"end":1116},"obj":"Chemical"},{"id":"1626","span":{"begin":1122,"end":1130},"obj":"Chemical"},{"id":"1627","span":{"begin":1136,"end":1139},"obj":"Chemical"},{"id":"1628","span":{"begin":1141,"end":1142},"obj":"Chemical"},{"id":"1629","span":{"begin":1160,"end":1161},"obj":"Chemical"},{"id":"1630","span":{"begin":1176,"end":1177},"obj":"Chemical"},{"id":"1631","span":{"begin":1195,"end":1196},"obj":"Chemical"},{"id":"1632","span":{"begin":1226,"end":1236},"obj":"Chemical"},{"id":"1633","span":{"begin":1204,"end":1208},"obj":"Disease"}],"attributes":[{"id":"A1623","pred":"tao:has_database_id","subj":"1623","obj":"MESH:D000432"},{"id":"A1624","pred":"tao:has_database_id","subj":"1624","obj":"MESH:D002725"},{"id":"A1626","pred":"tao:has_database_id","subj":"1626","obj":"MESH:D000432"},{"id":"A1628","pred":"tao:has_database_id","subj":"1628","obj":"MESH:D002244"},{"id":"A1629","pred":"tao:has_database_id","subj":"1629","obj":"MESH:D009584"},{"id":"A1630","pred":"tao:has_database_id","subj":"1630","obj":"MESH:D002244"},{"id":"A1631","pred":"tao:has_database_id","subj":"1631","obj":"MESH:D009584"}],"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":"N-((1S)-1-{[((1S)-3-(Benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3,3-dimethylbutyl)-4-methoxy-1H-indole-2-carboxamide (34)\nFollowing the procedure described for the preparation of N-[(1S)-2-[((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]-1-(cyclohexylmethyl)-2-oxoethyl]-4-methoxy-1H-indole-2-carboxamide but substituting N1-((1S)-3-(benzyloxy)-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)-N2-(tert-butoxycarbonyl)-4-methyl-l-leucinamide and making noncritical variations provided a golden syrup. This material was purified by Biotage MPLC (25 M column, 3% methanol/chloroform) to afford 173 mg (60%) of the title compound as an off-white foam. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (s, 1H), 8.43 (app t, J = 8 Hz, 2H), 7.62 (s, 1H), 7.32 (m, 6H), 7.08 (t, J = 8 Hz, 1H), 7.00 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.52 (m, 1H), 4.47–4.35 (m, 4H), 4.22 (d, J = 16 Hz, 1H), 3.87 (s, 3H), 3.05 (m, 2H), 2.28 (m, 1H), 2.06 (m, 1H), 1.93 (m, 1H), 1.64–1.57 (m, 3H), 0.92 (s, 9H); MS (ESI+) for C32H40N4O6m/z 577.2 (M + H)+; anal. calcd for C32H40N4O6·0.33 methanol·0.25 H2O: C, 65.62; H, 7.13; N, 9.47. Found: C, 65.65; H, 6.90; N, 9.58; HRMS (ESI+) calcd for C32H40N4O6 577.3021, found 577.3001."}