PMC:7571312 / 54682-55728 JSONTXT

{"target":"https://pubannotation.org/docs/sourcedb/PMC/sourceid/7571312","sourcedb":"PMC","sourceid":"7571312","source_url":"https://www.ncbi.nlm.nih.gov/pmc/7571312","text":"Following 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-methylbenzoic 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 92 mg (44%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 11.59 (d, J = 1.8 Hz, 1H), 8.63 (d, J = 8.1 Hz, 1H), 8.46 (d, J = 7.6 Hz, 1H), 7.87 (d, J = 8.1 Hz, 2H), 7.65 (s, 1H), 7.37 (d, J = 1.8 Hz, 1H), 7.34 (d, J = 8.3 Hz, 2H), 7.08 (t, J = 8.0 Hz, 1H), 6.97–7.01 (m, 1H), 6.50 (d, J = 7.8 Hz, 1H), 5.09 (s, 1H), 5.03–5.20 (m, 1H), 4.43–4.52 (m, 2H), 3.87 (s, 3H), 3.04–3.17 (m, 2H), 2.38 (s, 3H), 2.28–2.34 (m, 1H), 2.06–2.14 (m, 1H), 1.96–2.06 (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 C32H38N4O7m/z 591.2 (M + H)+. Anal. calcd for C32H38N4O7·0.10 H2O·0.11 DCM: C, 64.08; H, 6.43; N, 9.31. Found: C, 64.36; H, 6.41; N, 8.92.","tracks":[{"project":"LitCovid-PD-CLO","denotations":[{"id":"T484","span":{"begin":250,"end":251},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T485","span":{"begin":894,"end":896},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T486","span":{"begin":929,"end":934},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"attributes":[{"subj":"T484","pred":"source","obj":"LitCovid-PD-CLO"},{"subj":"T485","pred":"source","obj":"LitCovid-PD-CLO"},{"subj":"T486","pred":"source","obj":"LitCovid-PD-CLO"}]},{"project":"LitCovid-PD-CHEBI","denotations":[{"id":"T44136","span":{"begin":72,"end":79},"obj":"Chemical"},{"id":"T72315","span":{"begin":80,"end":93},"obj":"Chemical"},{"id":"T80123","span":{"begin":80,"end":82},"obj":"Chemical"},{"id":"T38371","span":{"begin":94,"end":102},"obj":"Chemical"},{"id":"T84329","span":{"begin":106,"end":112},"obj":"Chemical"},{"id":"T18805","span":{"begin":113,"end":118},"obj":"Chemical"},{"id":"T29990","span":{"begin":122,"end":125},"obj":"Chemical"},{"id":"T16489","span":{"begin":155,"end":168},"obj":"Chemical"},{"id":"T52074","span":{"begin":155,"end":160},"obj":"Chemical"},{"id":"T82193","span":{"begin":161,"end":168},"obj":"Chemical"},{"id":"T58673","span":{"begin":186,"end":206},"obj":"Chemical"},{"id":"T4356","span":{"begin":188,"end":206},"obj":"Chemical"},{"id":"T58977","span":{"begin":202,"end":206},"obj":"Chemical"},{"id":"T76679","span":{"begin":326,"end":334},"obj":"Chemical"},{"id":"T88844","span":{"begin":335,"end":350},"obj":"Chemical"},{"id":"T43261","span":{"begin":397,"end":399},"obj":"Chemical"},{"id":"T87223","span":{"begin":414,"end":418},"obj":"Chemical"},{"id":"T97389","span":{"begin":447,"end":449},"obj":"Chemical"},{"id":"T63097","span":{"begin":473,"end":475},"obj":"Chemical"},{"id":"T52721","span":{"begin":499,"end":501},"obj":"Chemical"},{"id":"T20525","span":{"begin":539,"end":541},"obj":"Chemical"},{"id":"T70463","span":{"begin":565,"end":567},"obj":"Chemical"},{"id":"T48645","span":{"begin":617,"end":619},"obj":"Chemical"},{"id":"T85643","span":{"begin":636,"end":638},"obj":"Chemical"},{"id":"T81008","span":{"begin":662,"end":664},"obj":"Chemical"},{"id":"T19507","span":{"begin":676,"end":678},"obj":"Chemical"},{"id":"T59206","span":{"begin":695,"end":697},"obj":"Chemical"},{"id":"T17149","span":{"begin":780,"end":782},"obj":"Chemical"},{"id":"T6479","span":{"begin":799,"end":801},"obj":"Chemical"},{"id":"T95796","span":{"begin":818,"end":820},"obj":"Chemical"},{"id":"T96393","span":{"begin":894,"end":896},"obj":"Chemical"},{"id":"T60033","span":{"begin":970,"end":973},"obj":"Chemical"},{"id":"T82823","span":{"begin":979,"end":982},"obj":"Chemical"}],"attributes":[{"id":"A61150","pred":"chebi_id","subj":"T44136","obj":"http://purl.obolibrary.org/obo/CHEBI_32772"},{"id":"A73241","pred":"chebi_id","subj":"T44136","obj":"http://purl.obolibrary.org/obo/CHEBI_44520"},{"id":"A57398","pred":"chebi_id","subj":"T72315","obj":"http://purl.obolibrary.org/obo/CHEBI_51611"},{"id":"A14132","pred":"chebi_id","subj":"T80123","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A77368","pred":"chebi_id","subj":"T38371","obj":"http://purl.obolibrary.org/obo/CHEBI_23019"},{"id":"A54045","pred":"chebi_id","subj":"T84329","obj":"http://purl.obolibrary.org/obo/CHEBI_32630"},{"id":"A59743","pred":"chebi_id","subj":"T84329","obj":"http://purl.obolibrary.org/obo/CHEBI_37904"},{"id":"A32917","pred":"chebi_id","subj":"T18805","obj":"http://purl.obolibrary.org/obo/CHEBI_46882"},{"id":"A83508","pred":"chebi_id","subj":"T29990","obj":"http://purl.obolibrary.org/obo/CHEBI_46629"},{"id":"A38123","pred":"chebi_id","subj":"T16489","obj":"http://purl.obolibrary.org/obo/CHEBI_31328"},{"id":"A31547","pred":"chebi_id","subj":"T52074","obj":"http://purl.obolibrary.org/obo/CHEBI_41264"},{"id":"A66310","pred":"chebi_id","subj":"T82193","obj":"http://purl.obolibrary.org/obo/CHEBI_30089"},{"id":"A55457","pred":"chebi_id","subj":"T82193","obj":"http://purl.obolibrary.org/obo/CHEBI_47622"},{"id":"A4621","pred":"chebi_id","subj":"T58673","obj":"http://purl.obolibrary.org/obo/CHEBI_36635"},{"id":"A81075","pred":"chebi_id","subj":"T4356","obj":"http://purl.obolibrary.org/obo/CHEBI_25280"},{"id":"A72622","pred":"chebi_id","subj":"T58977","obj":"http://purl.obolibrary.org/obo/CHEBI_37527"},{"id":"A22518","pred":"chebi_id","subj":"T76679","obj":"http://purl.obolibrary.org/obo/CHEBI_17790"},{"id":"A62533","pred":"chebi_id","subj":"T88844","obj":"http://purl.obolibrary.org/obo/CHEBI_15767"},{"id":"A13890","pred":"chebi_id","subj":"T43261","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A43010","pred":"chebi_id","subj":"T87223","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"},{"id":"A22739","pred":"chebi_id","subj":"T97389","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A99600","pred":"chebi_id","subj":"T63097","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A93932","pred":"chebi_id","subj":"T52721","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A87153","pred":"chebi_id","subj":"T20525","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A12269","pred":"chebi_id","subj":"T70463","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A80018","pred":"chebi_id","subj":"T48645","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A75776","pred":"chebi_id","subj":"T85643","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A47518","pred":"chebi_id","subj":"T81008","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A19426","pred":"chebi_id","subj":"T19507","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A57048","pred":"chebi_id","subj":"T59206","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A86022","pred":"chebi_id","subj":"T17149","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A38748","pred":"chebi_id","subj":"T6479","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A37913","pred":"chebi_id","subj":"T95796","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A83687","pred":"chebi_id","subj":"T96393","obj":"http://purl.obolibrary.org/obo/CHEBI_73613"},{"id":"A14028","pred":"chebi_id","subj":"T60033","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A93922","pred":"chebi_id","subj":"T82823","obj":"http://purl.obolibrary.org/obo/CHEBI_15767"},{"subj":"T44136","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T72315","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T80123","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T38371","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T84329","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T18805","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T29990","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T16489","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T52074","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T82193","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T58673","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T4356","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T58977","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T76679","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T88844","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T43261","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T87223","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T97389","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T63097","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T52721","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T20525","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T70463","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T48645","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T85643","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T81008","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T19507","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T59206","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T17149","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T6479","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T95796","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T96393","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T60033","pred":"source","obj":"LitCovid-PD-CHEBI"},{"subj":"T82823","pred":"source","obj":"LitCovid-PD-CHEBI"}]},{"project":"LitCovid-sentences","denotations":[{"id":"T354","span":{"begin":0,"end":266},"obj":"Sentence"},{"id":"T355","span":{"begin":267,"end":396},"obj":"Sentence"},{"id":"T356","span":{"begin":397,"end":937},"obj":"Sentence"},{"id":"T357","span":{"begin":938,"end":1011},"obj":"Sentence"},{"id":"T358","span":{"begin":1012,"end":1046},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"attributes":[{"subj":"T354","pred":"source","obj":"LitCovid-sentences"},{"subj":"T355","pred":"source","obj":"LitCovid-sentences"},{"subj":"T356","pred":"source","obj":"LitCovid-sentences"},{"subj":"T357","pred":"source","obj":"LitCovid-sentences"},{"subj":"T358","pred":"source","obj":"LitCovid-sentences"}]},{"project":"LitCovid-PD-HP","denotations":[{"id":"T8","span":{"begin":979,"end":982},"obj":"Phenotype"}],"attributes":[{"id":"A8","pred":"hp_id","subj":"T8","obj":"http://purl.obolibrary.org/obo/HP_0001644"},{"subj":"T8","pred":"source","obj":"LitCovid-PD-HP"}]},{"project":"LitCovid-PubTator","denotations":[{"id":"1238","span":{"begin":186,"end":206},"obj":"Chemical"},{"id":"1239","span":{"begin":326,"end":334},"obj":"Chemical"},{"id":"1240","span":{"begin":335,"end":350},"obj":"Chemical"},{"id":"1241","span":{"begin":954,"end":964},"obj":"Chemical"},{"id":"1242","span":{"begin":970,"end":973},"obj":"Chemical"},{"id":"1243","span":{"begin":979,"end":982},"obj":"Chemical"},{"id":"1244","span":{"begin":984,"end":985},"obj":"Chemical"},{"id":"1245","span":{"begin":1003,"end":1004},"obj":"Chemical"},{"id":"1246","span":{"begin":1019,"end":1020},"obj":"Chemical"},{"id":"1247","span":{"begin":1038,"end":1039},"obj":"Chemical"}],"attributes":[{"id":"A1238","pred":"tao:has_database_id","subj":"1238","obj":"MESH:C009504"},{"id":"A1239","pred":"tao:has_database_id","subj":"1239","obj":"MESH:D000432"},{"id":"A1240","pred":"tao:has_database_id","subj":"1240","obj":"MESH:D008752"},{"id":"A1243","pred":"tao:has_database_id","subj":"1243","obj":"MESH:D008752"},{"id":"A1244","pred":"tao:has_database_id","subj":"1244","obj":"MESH:D002244"},{"id":"A1245","pred":"tao:has_database_id","subj":"1245","obj":"MESH:D009584"},{"id":"A1246","pred":"tao:has_database_id","subj":"1246","obj":"MESH:D002244"},{"id":"A1247","pred":"tao:has_database_id","subj":"1247","obj":"MESH:D009584"},{"subj":"1238","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1239","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1240","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1241","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1242","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1243","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1244","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1245","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1246","pred":"source","obj":"LitCovid-PubTator"},{"subj":"1247","pred":"source","obj":"LitCovid-PubTator"}],"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_"}]}],"config":{"attribute types":[{"pred":"source","value type":"selection","values":[{"id":"LitCovid-PD-CLO","color":"#ccec93","default":true},{"id":"LitCovid-PD-CHEBI","color":"#ec93e6"},{"id":"LitCovid-sentences","color":"#93ecd7"},{"id":"LitCovid-PD-HP","color":"#ecbd93"},{"id":"LitCovid-PubTator","color":"#a393ec"}]}]}}