PMC:7571312 / 58042-59224 JSON TXT

Annnotations TAB JSON ListView MergeView

LitCovid-PD-CLO

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T493","span":{"begin":376,"end":377},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T494","span":{"begin":1026,"end":1028},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T495","span":{"begin":1063,"end":1068},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Chlorobenzoate (21)\nFollowing the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}

LitCovid-PD-CHEBI

LitCovid-sentences

{"project":"LitCovid-sentences","denotations":[{"id":"T371","span":{"begin":0,"end":125},"obj":"Sentence"},{"id":"T372","span":{"begin":126,"end":392},"obj":"Sentence"},{"id":"T373","span":{"begin":393,"end":523},"obj":"Sentence"},{"id":"T374","span":{"begin":524,"end":1071},"obj":"Sentence"},{"id":"T375","span":{"begin":1072,"end":1147},"obj":"Sentence"},{"id":"T376","span":{"begin":1148,"end":1182},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Chlorobenzoate (21)\nFollowing the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}

LitCovid-PD-HP

{"project":"LitCovid-PD-HP","denotations":[{"id":"T10","span":{"begin":1115,"end":1118},"obj":"Phenotype"}],"attributes":[{"id":"A10","pred":"hp_id","subj":"T10","obj":"http://purl.obolibrary.org/obo/HP_0001644"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Chlorobenzoate (21)\nFollowing the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}

LitCovid-PubTator

{"project":"LitCovid-PubTator","denotations":[{"id":"1296","span":{"begin":312,"end":332},"obj":"Chemical"},{"id":"1297","span":{"begin":452,"end":460},"obj":"Chemical"},{"id":"1298","span":{"begin":461,"end":476},"obj":"Chemical"},{"id":"1299","span":{"begin":1088,"end":1100},"obj":"Chemical"},{"id":"1300","span":{"begin":1106,"end":1109},"obj":"Chemical"},{"id":"1301","span":{"begin":1115,"end":1118},"obj":"Chemical"},{"id":"1302","span":{"begin":1120,"end":1121},"obj":"Chemical"},{"id":"1303","span":{"begin":1139,"end":1140},"obj":"Chemical"},{"id":"1304","span":{"begin":1155,"end":1156},"obj":"Chemical"},{"id":"1305","span":{"begin":1174,"end":1175},"obj":"Chemical"}],"attributes":[{"id":"A1296","pred":"tao:has_database_id","subj":"1296","obj":"MESH:C040768"},{"id":"A1297","pred":"tao:has_database_id","subj":"1297","obj":"MESH:D000432"},{"id":"A1298","pred":"tao:has_database_id","subj":"1298","obj":"MESH:D008752"},{"id":"A1301","pred":"tao:has_database_id","subj":"1301","obj":"MESH:D008752"},{"id":"A1302","pred":"tao:has_database_id","subj":"1302","obj":"MESH:D002244"},{"id":"A1303","pred":"tao:has_database_id","subj":"1303","obj":"MESH:D009584"},{"id":"A1304","pred":"tao:has_database_id","subj":"1304","obj":"MESH:D002244"},{"id":"A1305","pred":"tao:has_database_id","subj":"1305","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":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 4-Chlorobenzoate (21)\nFollowing the procedure described for the preparation of (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl acetate but substituting 4-chlorobenzoic acid and making noncritical variations provided a crude product. This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 172 mg (80%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.58 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 7.8 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.98 (d, J = 8.6 Hz, 2H), 7.65 (s, 1H), 7.62 (d, J = 8.6 Hz, 2H), 7.37 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.3 Hz, 1H), 6.50 (d, J = 7.6 Hz, 1H), 5.13 (d, J = 1.5 Hz, 1H), 5.07–5.23 (m, 1H), 4.44–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.14 (m, 2H), 2.28–2.38 (m, 1H), 2.06–2.26 (m, 1H), 1.97–2.06 (m, 1H), 1.51–1.78 (m, 5H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C31H35ClN4O7m/z 611.1 (M + H)+. Anal. calcd for C31H35ClN4O7·0.72 H2O·0.05 DCM: C, 59.36; H, 5.86; N, 8.92. Found: C, 59.31; H, 5.99; N, 9.23."}