> top > docs > PMC:7291971 > spans > 77445-79205 > annotations

PMC:7291971 / 77445-79205 JSONTXT

Annnotations TAB JSON ListView MergeView

LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T1559 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T1560 87-95 CHEBI:75958;CHEBI:75958 denotes solution
T1561 99-101 CHEBI:86228;CHEBI:86228 denotes 4-
T1562 101-107 CHEBI:47853;CHEBI:47853 denotes chloro
T1563 107-128 CHEBI:86228;CHEBI:86228 denotes -3-nitrobenazaldehyde
T1564 187-198 CHEBI:15366;CHEBI:15366 denotes acetic acid
T1565 276-282 CHEBI:35607;CHEBI:35607 denotes sodium
T1566 283-304 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T1567 382-390 CHEBI:75958;CHEBI:75958 denotes solution
T1568 446-453 CHEBI:15377;CHEBI:15377 denotes aqueous
T1569 454-460 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T1570 466-473 CHEBI:15377;CHEBI:15377 denotes aqueous
T1571 592-598 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T1572 687-693 CHEBI:30563;CHEBI:30563 denotes silica
T1573 720-724 CHEBI:32145;CHEBI:32145 denotes MeOH
T1574 785-789 CHEBI:32145;CHEBI:32145 denotes MeOH
T1575 818-823 CHEBI:30808;CHEBI:30808 denotes CDCl3
T1576 1398-1401 CHEBI:36927;CHEBI:36927 denotes 13C
T87653 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T87411 87-95 CHEBI:75958;CHEBI:75958 denotes solution
T67786 99-101 CHEBI:86228;CHEBI:86228 denotes 4-
T2415 101-107 CHEBI:47853;CHEBI:47853 denotes chloro
T47993 107-128 CHEBI:86228;CHEBI:86228 denotes -3-nitrobenazaldehyde
T2831 187-198 CHEBI:15366;CHEBI:15366 denotes acetic acid
T81538 276-282 CHEBI:35607;CHEBI:35607 denotes sodium
T68096 283-304 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T17174 382-390 CHEBI:75958;CHEBI:75958 denotes solution
T52438 446-453 CHEBI:15377;CHEBI:15377 denotes aqueous
T1797 454-460 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T62375 466-473 CHEBI:15377;CHEBI:15377 denotes aqueous
T33887 592-598 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T87343 687-693 CHEBI:30563;CHEBI:30563 denotes silica
T10295 720-724 CHEBI:32145;CHEBI:32145 denotes MeOH
T78188 785-789 CHEBI:32145;CHEBI:32145 denotes MeOH
T12440 818-823 CHEBI:30808;CHEBI:30808 denotes CDCl3
T3563 1398-1401 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1446 62-65 Chemical denotes DCE
1447 99-128 Chemical denotes 4-chloro-3-nitrobenazaldehyde
1448 170-173 Chemical denotes DCE
1449 187-198 Chemical denotes acetic acid MESH:D019342
1450 269-274 Chemical denotes argon MESH:D001128
1451 276-304 Chemical denotes sodium triacetoxyborohydride
1452 408-411 Chemical denotes DCM
1453 454-460 Chemical denotes NaHCO3 MESH:D017693
1454 499-502 Chemical denotes DCM
1455 566-571 Chemical denotes brine MESH:C017082
1456 592-598 Chemical denotes Na2SO4
1457 687-697 Chemical denotes silica gel MESH:D058428
1458 720-724 Chemical denotes MeOH
1459 728-731 Chemical denotes DCM
1460 785-789 Chemical denotes MeOH
1461 790-793 Chemical denotes DCM
1462 801-803 Chemical denotes 1H
1463 818-823 Chemical denotes CDCl3
1464 836-838 Chemical denotes 1H
1465 850-852 Chemical denotes 1H
1466 864-866 Chemical denotes 1H
1467 882-884 Chemical denotes 2H MESH:D003903
1468 901-903 Chemical denotes 2H MESH:D003903
1469 919-921 Chemical denotes 2H MESH:D003903
1470 1709-1725 Chemical denotes C44H66N12O9Si2Cl
1471 1682-1686 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T412 3-4 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T413 85-86 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T414 130-132 http://purl.obolibrary.org/obo/CLO_0050509 denotes 27
T415 532-539 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T416 532-539 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T417 741-743 http://purl.obolibrary.org/obo/CLO_0001000 denotes 35
T418 747-748 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T419 1727-1730 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T54842 5-13 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T87374 62-65 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T756 87-95 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T74109 101-107 Chemical denotes chloro http://purl.obolibrary.org/obo/CHEBI_47853
T5740 170-173 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T759 187-198 Chemical denotes acetic acid http://purl.obolibrary.org/obo/CHEBI_15366
T71199 194-198 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T32586 269-274 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T94488 276-282 Chemical denotes sodium http://purl.obolibrary.org/obo/CHEBI_26708
T52531 382-390 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T68791 408-411 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T58335 454-460 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T85038 499-502 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T7488 592-598 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T90420 687-693 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T12080 720-724 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T47925 728-731 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T16758 776-778 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T56935 785-789 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T65073 790-793 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T92650 801-803 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T24482 818-823 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T46322 836-838 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60945 850-852 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T82601 864-866 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95044 963-965 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T91404 989-991 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T68720 1028-1030 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T98770 1067-1069 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T97976 1093-1095 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70613 1132-1134 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T67635 1158-1160 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T41136 1197-1199 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38412 1237-1239 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T26872 1275-1277 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T56080 1416-1421 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T33 408-411 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T34 499-502 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T35 728-731 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T36 790-793 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T517 0-227 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 228-343 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 344-461 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 462-629 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 630-775 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 776-800 Sentence denotes Rf 0.71 (MeOH/DCM 5:95).
T523 801-1397 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 1398-1681 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 1682-1733 Sentence denotes HRMS (ESI+): m/z calcd for C44H66N12O9Si2Cl [M+H]+:
T526 1734-1750 Sentence denotes 997.4297, found:
T527 1751-1760 Sentence denotes 997.4327.