PMC:7571312 / 114267-115632 JSONTXT

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LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T66 0-1 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T67 378-380 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T68 397-398 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T69 676-677 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T70 1260-1262 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T71 1295-1300 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T96709 2-10 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T78225 34-41 Chemical denotes hydroxy http://purl.obolibrary.org/obo/CHEBI_43176
T53284 44-47 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T68087 78-84 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T34247 85-91 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T10126 92-97 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T17616 98-106 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T42313 108-121 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T23058 125-132 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T46947 133-142 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T8538 133-135 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48591 136-142 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T47040 145-156 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T81598 178-189 Chemical denotes iodomethane http://purl.obolibrary.org/obo/CHEBI_39282
T54246 215-221 Chemical denotes silver http://purl.obolibrary.org/obo/CHEBI_30512|http://purl.obolibrary.org/obo/CHEBI_9141
T62922 225-230 Chemical denotes oxide http://purl.obolibrary.org/obo/CHEBI_25741|http://purl.obolibrary.org/obo/CHEBI_29356
T18262 254-269 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T55045 312-314 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T54261 417-428 Chemical denotes iodomethane http://purl.obolibrary.org/obo/CHEBI_39282
T39240 541-556 Chemical denotes dichloromethane http://purl.obolibrary.org/obo/CHEBI_15767
T37635 583-588 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T76936 634-639 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T26520 761-769 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T88534 770-780 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T81841 849-851 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T79196 857-861 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T44195 878-880 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T55525 902-904 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68136 926-928 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T33267 940-942 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T64544 954-956 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T48541 978-980 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37058 1002-1004 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T31005 1026-1028 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T94988 1040-1042 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T13706 1054-1056 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85428 1079-1081 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T59647 1104-1106 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T85409 1160-1162 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T737 1174-1176 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68386 1188-1190 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T739 1260-1262 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T618 0-315 Sentence denotes A solution of N-((1S)-1-{[((1S)-3-hydroxy-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (185 mg, 0.39 mmol), iodomethane (0.12 mL, 2.0 mmol), and silver(I) oxide (182 mg, 0.79 mmol) in dichloromethane (12 mL) was placed under an atmosphere of N2.
T619 316-496 Sentence denotes The resulting black thick suspension was heated to reflux for 18 h, treated with a second portion of iodomethane (0.12 mL, 2.0 mmol), and returned to reflux for an additional 24 h.
T620 497-694 Sentence denotes The reaction was cooled to RT, diluted with dichloromethane (20 mL), washed once with water (20 mL), once with brine (20 mL), dried over MgSO4, filtered, and concentrated to give a crude tan solid.
T621 695-848 Sentence denotes This material was purified by Biotage MPLC (25 M column, 3.5–4.5% methanol/chloroform) to afford 19 mg (10%) of the title compound as an off-white solid.
T622 849-1365 Sentence denotes 1H NMR (DMSO-d6) δ 11.57 (s, 1H), 8.48 (d, J = 8 Hz, 1H), 8.40 (d, J = 8 Hz, 1H), 7.63 (s, 1H), 7.35 (s, 1H), 7.08 (t, J = 8 Hz, 1H), 6.99 (d, J = 8 Hz, 1H), 6.49 (d, J = 8 Hz, 1H), 4.47 (m, 1H), 4.38 (m, 1H), 4.25 (d, J = 16 Hz, 1H), 4.11 (d, J = 16 Hz, 1H), 3.87 (s, 3H), 3.23 (s, 3H), 3.08 (m, 2H), 2.31 (m, 1H), 2.08 (m, 1H), 1.92 (m, 1H), 1.72–1.51 (m, 5H), 0.93 (d, J = 8 Hz, 3H), 0.88 (d, J = 8 Hz, 3H); MS (ESI+) for C25H34N4O6m/z 487.2 (M + H)+; HRMS (ESI+) calcd for C25H34N4O6+H1 487.2551, found 487.2563.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
2038 417-428 Chemical denotes iodomethane MESH:C014055
2039 541-556 Chemical denotes dichloromethane MESH:D008752
2040 583-588 Chemical denotes water MESH:D014867
2041 608-613 Chemical denotes brine MESH:C017082
2042 634-639 Chemical denotes MgSO4 MESH:D008278
2043 761-769 Chemical denotes methanol MESH:D000432
2044 770-780 Chemical denotes chloroform MESH:D002725
2045 1304-1308 Disease denotes HRMS