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PMC:7291971 / 77167-79205 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T1530 46-48 CHEBI:30756;CHEBI:30756 denotes 9H
T1531 49-59 CHEBI:30756;CHEBI:30756 denotes purin-9-yl
T1532 60-84 CHEBI:53233;CHEBI:53233 denotes -2,2-dimethyl-tetrahydro
T1533 85-87 CHEBI:53233;CHEBI:53233 denotes 2H
T1534 103-114 CHEBI:86228;CHEBI:86228 denotes 3]dioxol-4-
T1535 114-117 CHEBI:53233;CHEBI:53233 denotes yl]
T1536 117-123 CHEBI:29309;CHEBI:29309 denotes methyl
T1537 126-128 CHEBI:86228;CHEBI:86228 denotes 4-
T1538 128-134 CHEBI:47853;CHEBI:47853 denotes chloro
T1539 134-149 CHEBI:86228;CHEBI:86228 denotes -3-nitrophenyl)
T1540 149-155 CHEBI:29309;CHEBI:29309 denotes methyl
T1541 155-156 CHEBI:86228;CHEBI:86228 denotes ]
T1542 156-161 CHEBI:46882;CHEBI:46882 denotes amino
T1543 162-168 CHEBI:42241;CHEBI:42241 denotes ethoxy
T1544 170-171 CHEBI:86228;CHEBI:86228 denotes 4
T1545 178-179 CHEBI:53233;CHEBI:53233 denotes -
T1546 179-197 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T1547 197-198 CHEBI:53233;CHEBI:53233 denotes )
T1548 198-201 CHEBI:29354;CHEBI:29354 denotes oxy
T1549 202-213 CHEBI:53233;CHEBI:53233 denotes -5-{[(tert-
T1550 213-231 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T1551 231-232 CHEBI:53233;CHEBI:53233 denotes )
T1552 232-235 CHEBI:29354;CHEBI:29354 denotes oxy
T1553 236-242 CHEBI:16625;CHEBI:16625 denotes methyl
T1554 243-255 CHEBI:53233;CHEBI:53233 denotes oxolan-2-yl]
T1555 256-258 CHEBI:29238;CHEBI:29238 denotes 9H
T1556 259-264 CHEBI:17939;CHEBI:17939 denotes purin
T1557 264-267 CHEBI:17369;CHEBI:17369 denotes -6-
T1558 267-272 CHEBI:32952;CHEBI:32952 denotes amine
T1559 283-291 CHEBI:75958;CHEBI:75958 denotes solution
T1560 365-373 CHEBI:75958;CHEBI:75958 denotes solution
T1561 377-379 CHEBI:86228;CHEBI:86228 denotes 4-
T1562 379-385 CHEBI:47853;CHEBI:47853 denotes chloro
T1563 385-406 CHEBI:86228;CHEBI:86228 denotes -3-nitrobenazaldehyde
T1564 465-476 CHEBI:15366;CHEBI:15366 denotes acetic acid
T1565 554-560 CHEBI:35607;CHEBI:35607 denotes sodium
T1566 561-582 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T1567 660-668 CHEBI:75958;CHEBI:75958 denotes solution
T1568 724-731 CHEBI:15377;CHEBI:15377 denotes aqueous
T1569 732-738 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T1570 744-751 CHEBI:15377;CHEBI:15377 denotes aqueous
T1571 870-876 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T1572 965-971 CHEBI:30563;CHEBI:30563 denotes silica
T1573 998-1002 CHEBI:32145;CHEBI:32145 denotes MeOH
T1574 1063-1067 CHEBI:32145;CHEBI:32145 denotes MeOH
T1575 1096-1101 CHEBI:30808;CHEBI:30808 denotes CDCl3
T1576 1676-1679 CHEBI:36927;CHEBI:36927 denotes 13C
T22187 46-48 CHEBI:30756;CHEBI:30756 denotes 9H
T61490 49-59 CHEBI:30756;CHEBI:30756 denotes purin-9-yl
T33609 60-84 CHEBI:53233;CHEBI:53233 denotes -2,2-dimethyl-tetrahydro
T72503 85-87 CHEBI:53233;CHEBI:53233 denotes 2H
T84826 103-114 CHEBI:86228;CHEBI:86228 denotes 3]dioxol-4-
T77669 114-117 CHEBI:53233;CHEBI:53233 denotes yl]
T74326 117-123 CHEBI:29309;CHEBI:29309 denotes methyl
T68910 126-128 CHEBI:86228;CHEBI:86228 denotes 4-
T29834 128-134 CHEBI:47853;CHEBI:47853 denotes chloro
T61527 134-149 CHEBI:86228;CHEBI:86228 denotes -3-nitrophenyl)
T2636 149-155 CHEBI:29309;CHEBI:29309 denotes methyl
T77144 155-156 CHEBI:86228;CHEBI:86228 denotes ]
T5108 156-161 CHEBI:46882;CHEBI:46882 denotes amino
T26563 162-168 CHEBI:42241;CHEBI:42241 denotes ethoxy
T54685 170-171 CHEBI:86228;CHEBI:86228 denotes 4
T28095 178-179 CHEBI:53233;CHEBI:53233 denotes -
T7577 179-197 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T76522 197-198 CHEBI:53233;CHEBI:53233 denotes )
T62588 198-201 CHEBI:29354;CHEBI:29354 denotes oxy
T93366 202-213 CHEBI:53233;CHEBI:53233 denotes -5-{[(tert-
T84385 213-231 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T90566 231-232 CHEBI:53233;CHEBI:53233 denotes )
T91292 232-235 CHEBI:29354;CHEBI:29354 denotes oxy
T24654 236-242 CHEBI:16625;CHEBI:16625 denotes methyl
T77065 243-255 CHEBI:53233;CHEBI:53233 denotes oxolan-2-yl]
T32349 256-258 CHEBI:29238;CHEBI:29238 denotes 9H
T22971 259-264 CHEBI:17939;CHEBI:17939 denotes purin
T77363 264-267 CHEBI:17369;CHEBI:17369 denotes -6-
T35102 267-272 CHEBI:32952;CHEBI:32952 denotes amine
T87653 283-291 CHEBI:75958;CHEBI:75958 denotes solution
T87411 365-373 CHEBI:75958;CHEBI:75958 denotes solution
T67786 377-379 CHEBI:86228;CHEBI:86228 denotes 4-
T2415 379-385 CHEBI:47853;CHEBI:47853 denotes chloro
T47993 385-406 CHEBI:86228;CHEBI:86228 denotes -3-nitrobenazaldehyde
T2831 465-476 CHEBI:15366;CHEBI:15366 denotes acetic acid
T81538 554-560 CHEBI:35607;CHEBI:35607 denotes sodium
T68096 561-582 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T17174 660-668 CHEBI:75958;CHEBI:75958 denotes solution
T52438 724-731 CHEBI:15377;CHEBI:15377 denotes aqueous
T1797 732-738 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T62375 744-751 CHEBI:15377;CHEBI:15377 denotes aqueous
T33887 870-876 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T87343 965-971 CHEBI:30563;CHEBI:30563 denotes silica
T10295 998-1002 CHEBI:32145;CHEBI:32145 denotes MeOH
T78188 1063-1067 CHEBI:32145;CHEBI:32145 denotes MeOH
T12440 1096-1101 CHEBI:30808;CHEBI:30808 denotes CDCl3
T3563 1676-1679 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1446 340-343 Chemical denotes DCE
1447 377-406 Chemical denotes 4-chloro-3-nitrobenazaldehyde
1448 448-451 Chemical denotes DCE
1449 465-476 Chemical denotes acetic acid MESH:D019342
1450 547-552 Chemical denotes argon MESH:D001128
1451 554-582 Chemical denotes sodium triacetoxyborohydride
1452 686-689 Chemical denotes DCM
1453 732-738 Chemical denotes NaHCO3 MESH:D017693
1454 777-780 Chemical denotes DCM
1455 844-849 Chemical denotes brine MESH:C017082
1456 870-876 Chemical denotes Na2SO4
1457 965-975 Chemical denotes silica gel MESH:D058428
1458 998-1002 Chemical denotes MeOH
1459 1006-1009 Chemical denotes DCM
1460 1063-1067 Chemical denotes MeOH
1461 1068-1071 Chemical denotes DCM
1462 1079-1081 Chemical denotes 1H
1463 1096-1101 Chemical denotes CDCl3
1464 1114-1116 Chemical denotes 1H
1465 1128-1130 Chemical denotes 1H
1466 1142-1144 Chemical denotes 1H
1467 1160-1162 Chemical denotes 2H MESH:D003903
1468 1179-1181 Chemical denotes 2H MESH:D003903
1469 1197-1199 Chemical denotes 2H MESH:D003903
1470 1987-2003 Chemical denotes C44H66N12O9Si2Cl
1471 1960-1964 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T411 274-276 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T412 281-282 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T413 363-364 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T414 408-410 http://purl.obolibrary.org/obo/CLO_0050509 denotes 27
T415 810-817 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T416 810-817 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T417 1019-1021 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T418 1025-1026 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T419 2005-2008 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T99640 38-59 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T29293 40-45 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T82586 65-73 Chemical denotes dimethyl http://purl.obolibrary.org/obo/CHEBI_33601|http://purl.obolibrary.org/obo/CHEBI_42266
T44634 117-123 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T38253 128-134 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T59769 149-155 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T51490 156-161 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T70758 162-168 Chemical denotes ethoxy http://purl.obolibrary.org/obo/CHEBI_42241
T748 198-201 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T35101 232-235 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T750 236-242 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T56159 256-272 Chemical denotes 9H-purin-6-amine http://purl.obolibrary.org/obo/CHEBI_16708
T40430 267-272 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T54842 283-291 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T87374 340-343 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T756 365-373 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T74109 379-385 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T5740 448-451 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T759 465-476 Chemical denotes acetic acid http://purl.obolibrary.org/obo/CHEBI_15366
T71199 472-476 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T32586 547-552 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T94488 554-560 Chemical denotes sodium http://purl.obolibrary.org/obo/CHEBI_26708
T52531 660-668 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T68791 686-689 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T58335 732-738 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T85038 777-780 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T7488 870-876 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T90420 965-971 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T12080 998-1002 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T47925 1006-1009 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T16758 1054-1056 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T56935 1063-1067 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T65073 1068-1071 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T92650 1079-1081 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24482 1096-1101 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T46322 1114-1116 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60945 1128-1130 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T82601 1142-1144 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95044 1241-1243 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91404 1267-1269 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68720 1306-1308 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98770 1345-1347 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T97976 1371-1373 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70613 1410-1412 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T67635 1436-1438 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T41136 1475-1477 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38412 1515-1517 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T26872 1553-1555 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56080 1694-1699 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T33 686-689 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T34 777-780 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T35 1006-1009 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T36 1068-1071 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T516 0-277 Sentence denotes 4.1.35 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}[(4-chloro-3-nitrophenyl)methyl]amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (35)
T517 278-505 Sentence denotes To a solution of 20 (100 mg, 0.12 mmol, 1.00 eq) in anhydrous DCE (3.5 mL) was added a solution of 4-chloro-3-nitrobenazaldehyde (27 mg, 0.18 mmol, 1.50 eq) in anhydrous DCE (3.5 mL) and acetic acid (10 μL, 0.18 mmol, 1.50 eq).
T518 506-621 Sentence denotes After stirring for 20 min at 40 °C under argon, sodium triacetoxyborohydride (38 mg, 0.18 mmol, 1.50 eq) was added.
T519 622-739 Sentence denotes After stirring at 40 °C for 16 h, the solution was diluted with DCM (30 mL) and washed with saturated aqueous NaHCO3.
T520 740-907 Sentence denotes The aqueous layer was extracted with DCM (3 × 30 mL) and the combined organic extracts were washed with brine (60 mL), dried over Na2SO4 and concentrated under vacuum.
T521 908-1053 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–5% MeOH in DCM) to give 35 as a white solid (105 mg, 87%).
T522 1054-1078 Sentence denotes Rf 0.71 (MeOH/DCM 5:95).
T523 1079-1675 Sentence denotes 1H NMR (500 MHz, CDCl3) δ 8.27 (s, 1H), 8.18 (s, 1H), 8.15 (s, 1H), 7.82 (br. s, 2H), 7.29–7.27 (m, 2H), 6.22 (br. s, 2H), 6.20 (br. s, 2H), 6.10 (d, J = 3.6 Hz, 1H), 5.99 (d, J = 2.1 Hz, 1H), 5.37 (dd, J = 6.5 Hz, J = 2.1 Hz, 1H), 4.91 (dd, J = 6.5 Hz, J = 3.7 Hz, 1H), 4.48 (t, J = 5.1 Hz, 1H), 4.30 (td, J = 6.7 Hz, J = 3.6 Hz, 1H), 4.22 (t, J = 4.2 Hz, 1H), 4.07 (dt, J = 5.8 Hz, J = 3.0 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.4 Hz, 1H), 3.81–3.72 (m, 2H), 3.71–3.66 (m, 1H), 3.65–3.61 (m, 2H), 2.90–2.70 (m, 4H), 1.57 (s, 3H), 1.36 (s, 3H), 0.92 (s, 9H), 0.86 (s, 9H), 0.14 – - 0.02 (m, 12H).
T524 1676-1959 Sentence denotes 13C NMR (125 MHz, CDCl3) δ 155.8, 155.7, 153.1, 153.0, 149.6, 149.0, 147.8, 140.6, 140.1, 139.3, 133.0, 131.4, 125.6, 125.2, 120.3, 120.1, 114.6, 90.8, 87.0, 85.7, 84.9, 84.0, 83.4, 82.8, 69.6, 69.3, 61.8, 58.2, 56.4, 53.5, 27.2, 26.2, 25.8, 25.4, 18.6, 18.2, −4.5, −4.7, −5.2, −5.3.
T525 1960-2011 Sentence denotes HRMS (ESI+): m/z calcd for C44H66N12O9Si2Cl [M+H]+:
T526 2012-2028 Sentence denotes 997.4297, found:
T527 2029-2038 Sentence denotes 997.4327.