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PMC:7571312 / 82001-83918 JSONTXT

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LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T598 147-148 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T599 870-871 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T600 891-893 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T601 926-931 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H
T602 935-936 http://purl.obolibrary.org/obo/CLO_0001020 denotes A
T603 1288-1289 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T604 1874-1876 http://purl.obolibrary.org/obo/CLO_0007874 denotes MS
T605 1909-1914 http://purl.obolibrary.org/obo/CLO_0007706 denotes M + H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T1272 30-33 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1273 64-70 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1275 71-77 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1276 78-83 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1277 84-92 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1278 94-107 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1279 111-118 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1281 119-128 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1282 119-121 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1283 122-128 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1284 131-142 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1286 149-157 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1287 181-187 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T1288 190-193 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1289 224-230 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T1291 231-237 Chemical denotes propyl http://purl.obolibrary.org/obo/CHEBI_26308
T1292 238-243 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1293 244-252 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1294 254-267 Chemical denotes 3-methylbutyl http://purl.obolibrary.org/obo/CHEBI_30359
T1295 271-278 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1297 279-288 Chemical denotes 1H-indole http://purl.obolibrary.org/obo/CHEBI_16881
T1298 279-281 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1299 282-288 Chemical denotes indole http://purl.obolibrary.org/obo/CHEBI_35581
T1300 291-302 Chemical denotes carboxamide http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622
T1302 341-345 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T1303 368-371 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T1304 415-417 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1305 442-450 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1306 468-474 Chemical denotes cesium http://purl.obolibrary.org/obo/CHEBI_30514
T1307 475-483 Chemical denotes fluoride http://purl.obolibrary.org/obo/CHEBI_17051
T1308 601-614 Chemical denotes ethyl acetate http://purl.obolibrary.org/obo/CHEBI_27750
T1309 601-606 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T1311 607-614 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1313 648-653 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T1314 702-707 Chemical denotes MgSO4 http://purl.obolibrary.org/obo/CHEBI_32599
T1315 759-766 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1317 767-780 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T1318 767-769 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1319 781-789 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1320 793-799 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T1322 800-805 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1323 809-812 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1324 842-847 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1325 848-866 Chemical denotes oxo(phenyl)acetate http://purl.obolibrary.org/obo/CHEBI_36656
T1326 848-851 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1327 852-858 Chemical denotes phenyl http://purl.obolibrary.org/obo/CHEBI_30396
T1328 859-866 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1330 891-893 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613
T1331 937-945 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T1332 974-981 Chemical denotes methoxy http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520
T1334 982-995 Chemical denotes 1H-indol-2-yl http://purl.obolibrary.org/obo/CHEBI_51611
T1335 982-984 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1336 996-1004 Chemical denotes carbonyl http://purl.obolibrary.org/obo/CHEBI_23019
T1337 1008-1014 Chemical denotes leucyl http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904
T1339 1015-1020 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T1340 1024-1027 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1341 1057-1062 Chemical denotes butyl http://purl.obolibrary.org/obo/CHEBI_41264
T1342 1063-1081 Chemical denotes oxo(phenyl)acetate http://purl.obolibrary.org/obo/CHEBI_36656
T1343 1063-1066 Chemical denotes oxo http://purl.obolibrary.org/obo/CHEBI_46629
T1344 1067-1073 Chemical denotes phenyl http://purl.obolibrary.org/obo/CHEBI_30396
T1345 1074-1081 Chemical denotes acetate http://purl.obolibrary.org/obo/CHEBI_30089|http://purl.obolibrary.org/obo/CHEBI_47622
T1347 1085-1093 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1348 1136-1138 Chemical denotes N2 http://purl.obolibrary.org/obo/CHEBI_17997
T1349 1156-1175 Chemical denotes potassium carbonate http://purl.obolibrary.org/obo/CHEBI_131526
T1350 1156-1165 Chemical denotes potassium http://purl.obolibrary.org/obo/CHEBI_26216
T1351 1166-1175 Chemical denotes carbonate http://purl.obolibrary.org/obo/CHEBI_41609
T1352 1370-1378 Chemical denotes methanol http://purl.obolibrary.org/obo/CHEBI_17790
T1353 1379-1389 Chemical denotes chloroform http://purl.obolibrary.org/obo/CHEBI_35255
T1354 1459-1461 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1355 1467-1471 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T1356 1488-1490 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1357 1512-1514 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1358 1536-1538 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1359 1550-1552 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1360 1564-1566 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1361 1588-1590 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1362 1612-1614 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1363 1636-1638 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1364 1660-1662 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1365 1703-1705 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1366 1732-1734 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1367 1774-1776 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1368 1788-1790 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1369 1802-1804 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1370 1874-1876 Chemical denotes MS http://purl.obolibrary.org/obo/CHEBI_73613

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T485 0-146 Sentence denotes 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 (4)
T486 147-418 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 419-532 Sentence denotes This clear pale yellow solution was treated with cesium fluoride (350 mg, 2.3 mmol) followed by heating to 65 °C.
T488 533-890 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 891-934 Sentence denotes MS (ESI+) for C32H36N4O8m/z 605.2 (M + H)+.
T490 935-1217 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 1218-1309 Sentence denotes After 1 h, the volatiles were removed in vacuo (bath < 30 °C) to give a crude yellow glass.
T492 1310-1458 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 1459-1917 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 648-653 Chemical denotes water MESH:D014867
1682 905-916 Chemical denotes C32H36N4O8m
1683 1085-1093 Chemical denotes methanol MESH:D000432
1684 1136-1138 Chemical denotes N2
1685 1156-1175 Chemical denotes potassium carbonate MESH:C037593
1686 1370-1378 Chemical denotes methanol MESH:D000432
1687 1379-1389 Chemical denotes chloroform MESH:D002725