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PMC:7571312 / 82148-83918 JSONTXT

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LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T598 0-1 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T599 723-724 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T600 744-746 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T601 779-784 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T602 788-789 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T603 1141-1142 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T604 1727-1729 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T605 1762-1767 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T1286 2-10 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1287 34-40 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1288 43-46 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1289 77-83 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1291 84-90 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1292 91-96 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1293 97-105 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1294 107-120 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1295 124-131 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1297 132-141 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1298 132-134 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1299 135-141 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1300 144-155 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1302 194-198 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T1303 221-224 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T1304 268-270 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1305 295-303 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1306 321-327 Chemical denotes cesium http://purl.obolibrary.org/obo/CHEBI_30514
T1307 328-336 Chemical denotes fluoride http://purl.obolibrary.org/obo/CHEBI_17051
T1308 454-467 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T1309 454-459 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T1311 460-467 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1313 501-506 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T1314 555-560 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T1315 612-619 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1317 620-633 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T1318 620-622 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1319 634-642 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1320 646-652 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T1322 653-658 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1323 662-665 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1324 695-700 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1325 701-719 Chemical denotes oxo(phenyl)acetate http://purl.obolibrary.org/obo/CHEBI_36656
T1326 701-704 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1327 705-711 Chemical denotes phenyl http://purl.obolibrary.org/obo/CHEBI_30396
T1328 712-719 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1330 744-746 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1331 790-798 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1332 827-834 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1334 835-848 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T1335 835-837 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1336 849-857 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1337 861-867 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T1339 868-873 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1340 877-880 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1341 910-915 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1342 916-934 Chemical denotes oxo(phenyl)acetate http://purl.obolibrary.org/obo/CHEBI_36656
T1343 916-919 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1344 920-926 Chemical denotes phenyl http://purl.obolibrary.org/obo/CHEBI_30396
T1345 927-934 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1347 938-946 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1348 989-991 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1349 1009-1028 Chemical denotes potassium carbonate http://purl.obolibrary.org/obo/CHEBI_131526
T1350 1009-1018 Chemical denotes potassium http://purl.obolibrary.org/obo/CHEBI_26216
T1351 1019-1028 Chemical denotes carbonate http://purl.obolibrary.org/obo/CHEBI_41609
T1352 1223-1231 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1353 1232-1242 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1354 1312-1314 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1355 1320-1324 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1356 1341-1343 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1357 1365-1367 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1358 1389-1391 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1359 1403-1405 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1360 1417-1419 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1361 1441-1443 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1362 1465-1467 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1363 1489-1491 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1364 1513-1515 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1365 1556-1558 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1366 1585-1587 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1367 1627-1629 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1368 1641-1643 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1369 1655-1657 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1370 1727-1729 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T486 0-271 Sentence denotes A solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (488 mg, 0.99 mmol) and benzoylformic acid (195 mg, 1.3 mmol) in DMF (6.5 mL) was placed under an atmosphere of N2.
T487 272-385 Sentence denotes This clear pale yellow solution was treated with cesium fluoride (350 mg, 2.3 mmol) followed by heating to 65 °C.
T488 386-743 Sentence denotes After 4 h, the now yellow suspension was cooled to RT, diluted with ethyl acetate (60 mL), washed three times with water (30 mL) and once with brine (30 mL), dried over MgSO4, filtered, and concentrated to give (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl oxo(phenyl)acetate as a crude yellow foam.
T489 744-787 Sentence denotes MS (ESI+) for C32H36N4O8m/z 605.2 (M + H)+.
T490 788-1070 Sentence denotes A solution of the crude (3S)-3-({N-[(4-methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl oxo(phenyl)acetate in methanol (40 mL) was placed under an atmosphere of N2 and treated with potassium carbonate (7 mg, 0.05 mmol) with vigorous stirring.
T491 1071-1162 Sentence denotes After 1 h, the volatiles were removed in vacuo (bath < 30 °C) to give a crude yellow glass.
T492 1163-1311 Sentence denotes This material was purified by Biotage MPLC (25 M column, 6% methanol/chloroform) to afford 346 mg (73%) of the title compound as an off-white solid.
T493 1312-1770 Sentence denotes 1H NMR (DMSO-d6) δ 11.56 (s, 1H), 8.44 (d, J = 8 Hz, 1H), 8.39 (d, J = 8 Hz, 1H), 7.61 (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), 5.04 (t, J = 8 Hz, 1H), 4.46 (m, 2H), 4.25 (dd, J = 8, 20 Hz, 1H), 4.13 (dd, J = 8, 20 Hz, 1H), 3.87 (s, 3H), 3.10 (m, 2H), 2.28 (m, 1H), 2.08 (m, 1H), 1.92 (m, 1H), 1.70–1.53 (m, 5H), 0.93 (d, J = 8 Hz, 3H), 0.89 (d, J = 8 Hz, 3H); MS (ESI+) for C24H32N4O6m/z 473.2 (M + H)+.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1681 501-506 Chemical denotes water MESH:D014867
1682 758-769 Chemical denotes C32H36N4O8m
1683 938-946 Chemical denotes methanol MESH:D000432
1684 989-991 Chemical denotes N2
1685 1009-1028 Chemical denotes potassium carbonate MESH:C037593
1686 1223-1231 Chemical denotes methanol MESH:D000432
1687 1232-1242 Chemical denotes chloroform MESH:D002725