PMC:7571312 / 66078-67185 JSONTXT

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T524","span":{"begin":374,"end":375},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T525","span":{"begin":472,"end":483},"obj":"http://purl.obolibrary.org/obo/CLO_0007698"},{"id":"T526","span":{"begin":506,"end":507},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T527","span":{"begin":901,"end":903},"obj":"http://purl.obolibrary.org/obo/CLO_0007874"},{"id":"T528","span":{"begin":936,"end":941},"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 2-Cyanobenzoate (28)\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 2-cyanobenzoic acid and making noncritical variations provided a crude brown oily solid. This material was triturated with chloroform/ethyl acetate to afford 91 mg (38%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.65 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 8.17 (m, 1H), 8.04 (m, 1H), 7.88 (m, 1H), 7.65 (s, 1H), 7.37 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.19 (m, 2H), 4.50 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.32 (m, 1H), 2.07–1.97 (m, 2H), 1.76–1.56 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+; anal. calcd for C32H35N5O7·0.4 H2O: C, 63.12, H, 5.93; N, 11.50. Found: C, 63.16; H, 5.96; N, 11.43; HRMS (ESI+) calcd for C32H35N5O7+H1 602.2609, found 602.2610."}

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"chebi_id","subj":"T64172","obj":"http://purl.obolibrary.org/obo/CHEBI_62801"},{"id":"A70494","pred":"chebi_id","subj":"T44252","obj":"http://purl.obolibrary.org/obo/CHEBI_30089"},{"id":"A43119","pred":"chebi_id","subj":"T44252","obj":"http://purl.obolibrary.org/obo/CHEBI_47622"},{"id":"A18902","pred":"chebi_id","subj":"T46481","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A60370","pred":"chebi_id","subj":"T72289","obj":"http://purl.obolibrary.org/obo/CHEBI_28262"},{"id":"A81980","pred":"chebi_id","subj":"T666","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A94605","pred":"chebi_id","subj":"T89315","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A90225","pred":"chebi_id","subj":"T57495","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A18110","pred":"chebi_id","subj":"T44704","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A32847","pred":"chebi_id","subj":"T670","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A64776","pred":"chebi_id","subj":"T671","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A12425","pred":"chebi_id","subj":"T27257","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A8995","pred":"chebi_id","subj":"T46988","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A55100","pred":"chebi_id","subj":"T674","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A31266","pred":"chebi_id","subj":"T675","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A24648","pred":"chebi_id","subj":"T94853","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A91595","pred":"chebi_id","subj":"T63231","obj":"http://purl.obolibrary.org/obo/CHEBI_49637"},{"id":"A56314","pred":"chebi_id","subj":"T16286","obj":"http://purl.obolibrary.org/obo/CHEBI_73613"},{"id":"A56653","pred":"chebi_id","subj":"T14704","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"}],"text":"(3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl 2-Cyanobenzoate (28)\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 2-cyanobenzoic acid and making noncritical variations provided a crude brown oily solid. This material was triturated with chloroform/ethyl acetate to afford 91 mg (38%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.65 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 8.17 (m, 1H), 8.04 (m, 1H), 7.88 (m, 1H), 7.65 (s, 1H), 7.37 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.19 (m, 2H), 4.50 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.32 (m, 1H), 2.07–1.97 (m, 2H), 1.76–1.56 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+; anal. calcd for C32H35N5O7·0.4 H2O: C, 63.12, H, 5.93; N, 11.50. Found: C, 63.16; H, 5.96; N, 11.43; HRMS (ESI+) calcd for C32H35N5O7+H1 602.2609, found 602.2610."}

{"project":"LitCovid-sentences","denotations":[{"id":"T409","span":{"begin":0,"end":124},"obj":"Sentence"},{"id":"T410","span":{"begin":125,"end":399},"obj":"Sentence"},{"id":"T411","span":{"begin":400,"end":520},"obj":"Sentence"},{"id":"T412","span":{"begin":521,"end":1009},"obj":"Sentence"},{"id":"T413","span":{"begin":1010,"end":1107},"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 2-Cyanobenzoate (28)\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 2-cyanobenzoic acid and making noncritical variations provided a crude brown oily solid. This material was triturated with chloroform/ethyl acetate to afford 91 mg (38%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.65 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 8.17 (m, 1H), 8.04 (m, 1H), 7.88 (m, 1H), 7.65 (s, 1H), 7.37 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.19 (m, 2H), 4.50 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.32 (m, 1H), 2.07–1.97 (m, 2H), 1.76–1.56 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+; anal. calcd for C32H35N5O7·0.4 H2O: C, 63.12, H, 5.93; N, 11.50. Found: C, 63.16; H, 5.96; N, 11.43; HRMS (ESI+) calcd for C32H35N5O7+H1 602.2609, found 602.2610."}

{"project":"LitCovid-PubTator","denotations":[{"id":"1439","span":{"begin":311,"end":330},"obj":"Chemical"},{"id":"1440","span":{"begin":434,"end":444},"obj":"Chemical"},{"id":"1441","span":{"begin":445,"end":458},"obj":"Chemical"},{"id":"1442","span":{"begin":961,"end":971},"obj":"Chemical"},{"id":"1443","span":{"begin":976,"end":979},"obj":"Chemical"},{"id":"1444","span":{"begin":981,"end":982},"obj":"Chemical"},{"id":"1445","span":{"begin":1000,"end":1001},"obj":"Chemical"},{"id":"1446","span":{"begin":1017,"end":1018},"obj":"Chemical"},{"id":"1447","span":{"begin":1036,"end":1037},"obj":"Chemical"},{"id":"1448","span":{"begin":1068,"end":1078},"obj":"Chemical"},{"id":"1449","span":{"begin":1046,"end":1050},"obj":"Disease"}],"attributes":[{"id":"A1440","pred":"tao:has_database_id","subj":"1440","obj":"MESH:D002725"},{"id":"A1441","pred":"tao:has_database_id","subj":"1441","obj":"MESH:C007650"},{"id":"A1444","pred":"tao:has_database_id","subj":"1444","obj":"MESH:D002244"},{"id":"A1445","pred":"tao:has_database_id","subj":"1445","obj":"MESH:D009584"},{"id":"A1446","pred":"tao:has_database_id","subj":"1446","obj":"MESH:D002244"},{"id":"A1447","pred":"tao:has_database_id","subj":"1447","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 2-Cyanobenzoate (28)\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 2-cyanobenzoic acid and making noncritical variations provided a crude brown oily solid. This material was triturated with chloroform/ethyl acetate to afford 91 mg (38%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 11.58 (s, 1H), 8.65 (d, J = 8 Hz, 1H), 8.46 (d, J = 8 Hz, 1H), 8.17 (m, 1H), 8.04 (m, 1H), 7.88 (m, 1H), 7.65 (s, 1H), 7.37 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 5.19 (m, 2H), 4.50 (m, 2H), 3.87 (s, 3H), 3.11 (m, 2H), 2.32 (m, 1H), 2.07–1.97 (m, 2H), 1.76–1.56 (m, 5H), 0.94 (d, J = 6 Hz, 3H), 0.89 (d, J = 6 Hz, 3H); MS (ESI+) for C32H35N5O7m/z 602.2 (M + H)+; anal. calcd for C32H35N5O7·0.4 H2O: C, 63.12, H, 5.93; N, 11.50. Found: C, 63.16; H, 5.96; N, 11.43; HRMS (ESI+) calcd for C32H35N5O7+H1 602.2609, found 602.2610."}