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PMC:7291971 / 79477-81147 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T1604 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T1605 85-103 CHEBI:28105;CHEBI:28105 denotes chlorobenzaldehyde
T1606 160-171 CHEBI:15366;CHEBI:15366 denotes acetic acid
T1607 249-255 CHEBI:35607;CHEBI:35607 denotes sodium
T1608 256-277 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T1609 355-363 CHEBI:75958;CHEBI:75958 denotes solution
T1610 419-426 CHEBI:15377;CHEBI:15377 denotes aqueous
T1611 427-433 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T1612 439-446 CHEBI:15377;CHEBI:15377 denotes aqueous
T1613 565-571 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T1614 660-666 CHEBI:30563;CHEBI:30563 denotes silica
T1615 693-697 CHEBI:32145;CHEBI:32145 denotes MeOH
T1616 769-773 CHEBI:32145;CHEBI:32145 denotes MeOH
T1617 805-810 CHEBI:30808;CHEBI:30808 denotes CDCl3
T1618 1322-1325 CHEBI:36927;CHEBI:36927 denotes 13C
T88984 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T47720 85-103 CHEBI:28105;CHEBI:28105 denotes chlorobenzaldehyde
T55812 160-171 CHEBI:15366;CHEBI:15366 denotes acetic acid
T35920 249-255 CHEBI:35607;CHEBI:35607 denotes sodium
T25301 256-277 CHEBI:28621;CHEBI:28621 denotes triacetoxyborohydride
T82736 355-363 CHEBI:75958;CHEBI:75958 denotes solution
T62757 419-426 CHEBI:15377;CHEBI:15377 denotes aqueous
T3173 427-433 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T55909 439-446 CHEBI:15377;CHEBI:15377 denotes aqueous
T40813 565-571 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T94720 660-666 CHEBI:30563;CHEBI:30563 denotes silica
T85547 693-697 CHEBI:32145;CHEBI:32145 denotes MeOH
T43861 769-773 CHEBI:32145;CHEBI:32145 denotes MeOH
T67038 805-810 CHEBI:30808;CHEBI:30808 denotes CDCl3
T80677 1322-1325 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1490 62-65 Chemical denotes DCE
1491 83-103 Chemical denotes 4-chlorobenzaldehyde MESH:C052044
1492 145-148 Chemical denotes DCE
1493 160-171 Chemical denotes acetic acid MESH:D019342
1494 242-247 Chemical denotes argon MESH:D001128
1495 249-277 Chemical denotes sodium triacetoxyborohydride
1496 381-384 Chemical denotes DCM
1497 427-433 Chemical denotes NaHCO3 MESH:D017693
1498 472-475 Chemical denotes DCM
1499 539-544 Chemical denotes brine MESH:C017082
1500 565-571 Chemical denotes Na2SO4
1501 660-670 Chemical denotes silica gel MESH:D058428
1502 693-697 Chemical denotes MeOH
1503 701-704 Chemical denotes DCM
1504 769-773 Chemical denotes MeOH
1505 774-780 Chemical denotes CH2Cl2
1506 1619-1635 Chemical denotes C44H67N11O7Si2Cl
1507 1592-1596 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T421 3-4 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T422 173-175 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T423 505-512 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T424 505-512 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T425 714-716 http://purl.obolibrary.org/obo/CLO_0001313 denotes 36
T426 720-721 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T427 1637-1640 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T44833 5-13 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T58625 62-65 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T43549 83-103 Chemical denotes 4-chlorobenzaldehyde http://purl.obolibrary.org/obo/CHEBI_28105
T25852 145-148 Chemical denotes DCE http://purl.obolibrary.org/obo/CHEBI_27789
T810 160-171 Chemical denotes acetic acid http://purl.obolibrary.org/obo/CHEBI_15366
T10046 167-171 Chemical denotes acid http://purl.obolibrary.org/obo/CHEBI_37527
T48049 242-247 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T71134 249-255 Chemical denotes sodium http://purl.obolibrary.org/obo/CHEBI_26708
T97988 355-363 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T71462 381-384 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T34804 427-433 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T68978 472-475 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T83602 565-571 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T96745 660-666 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T87703 693-697 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T12735 701-704 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T3817 760-762 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T45120 769-773 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T77370 788-790 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T19055 805-810 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T59650 823-825 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T38510 837-839 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T1609 851-853 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T45876 865-867 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T41693 910-912 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T29338 936-938 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T74783 994-996 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T30652 1033-1035 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46105 1059-1061 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T46041 1098-1100 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T71804 1124-1126 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T71447 1163-1165 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43485 1203-1205 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35540 1340-1345 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T37 381-384 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T38 472-475 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T39 701-704 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T529 0-200 Sentence denotes To a solution of 20 (210 mg, 0.25 mmol, 1.00 eq) in anhydrous DCE (7 mL) was added 4-chlorobenzaldehyde (43 mg, 0.38 mmol, 1.50 eq) in anhydrous DCE (7 mL) and acetic acid (18 μL, 0.38 mmol, 1.50 eq).
T530 201-316 Sentence denotes After stirring for 20 min at 40 °C under argon, sodium triacetoxyborohydride (81 mg, 0.38 mmol, 1.50 eq) was added.
T531 317-434 Sentence denotes After stirring at 40 °C for 16 h, the solution was diluted with DCM (50 mL) and washed with saturated aqueous NaHCO3.
T532 435-602 Sentence denotes The aqueous layer was extracted with DCM (3 × 50 mL) and the combined organic extracts were washed with brine (70 mL), dried over Na2SO4 and concentrated under vacuum.
T533 603-759 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–5% MeOH in DCM) to give 36 as a white solid (172 mg, 0.18 mmol, 72%).
T534 760-787 Sentence denotes Rf 0.71 (MeOH/CH2Cl2 5:95).
T535 788-1321 Sentence denotes 1H NMR (600 MHz, CDCl3) δ 8.30 (s, 1H), 8.20 (s, 1H), 8.15 (s, 1H), 7.83 (s, 1H), 7.19–7.07 (m, 4H), 6.11 (d, J = 3.7 Hz, 1H), 5.99 (d, J = 2.2 Hz, 1H), 5.97–5.83 (m, 4H), 5.37 (dd, J = 6.5 Hz, J = 2.2 Hz, 1H), 4.85 (dd, J = 6.4 Hz, J = 3.4 Hz, 1H), 4.49 (t, J = 5.1 Hz, 1H), 4.32 (td, J = 6.7 Hz, J = 3.3 Hz, 1H), 4.26 (t, J = 4.2 Hz, 1H), 4.08 (dt, J = 5.9 Hz, J = 3.1 Hz, 1H), 3.98 (dd, J = 11.5 Hz, J = 3.6 Hz, 1H), 3.79–3.47 (m, 5H), 2.84–2.66 (m, 4H), 1.58 (s, 3H), 1.36 (s, 3H), 0.92 (s, 9H), 0.88 (s, 9H), 0.13–0.02 (m, 12H).
T536 1322-1591 Sentence denotes 13C NMR (150 MHz, CDCl3) δ 155.7, 155.6, 153.1, 153.1, 149.7, 149.3, 140.0, 139.5, 137.8, 132.8, 130.1, 128.4, 120.5, 120.3, 114.4, 91.0, 87.2, 85.7, 84.9, 84.0, 83.5, 82.7, 69.8, 69.5, 61.3, 58.6, 56.4, 53.6, 27.3, 26.2, 25.9, 25.5, 18.6, 18.2, −4.5, −4.7, −5.2, −5.3.
T537 1592-1643 Sentence denotes HRMS (ESI+): m/z calcd for C44H67N11O7Si2Cl [M+H]+:
T538 1644-1660 Sentence denotes 952.4447, found:
T539 1661-1670 Sentence denotes 952.4426.