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PMC:7291971 / 39041-40469 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T821 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T822 84-89 CHEBI:32031;CHEBI:32031 denotes K2CO3
T823 122-132 CHEBI:48498;CHEBI:48498 denotes thiophenol
T824 231-238 CHEBI:60004;CHEBI:60004 denotes mixture
T825 288-295 CHEBI:15377;CHEBI:15377 denotes aqueous
T826 296-300 CHEBI:32145;CHEBI:32145 denotes NaOH
T827 301-309 CHEBI:75958;CHEBI:75958 denotes solution
T828 323-330 CHEBI:15377;CHEBI:15377 denotes aqueous
T829 441-447 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T830 536-542 CHEBI:30563;CHEBI:30563 denotes silica
T831 570-574 CHEBI:32145;CHEBI:32145 denotes MeOH
T832 654-658 CHEBI:32145;CHEBI:32145 denotes MeOH
T833 682-687 CHEBI:30808;CHEBI:30808 denotes CDCl3
T834 1121-1124 CHEBI:36927;CHEBI:36927 denotes 13C
T10400 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T2918 84-89 CHEBI:32031;CHEBI:32031 denotes K2CO3
T54095 122-132 CHEBI:48498;CHEBI:48498 denotes thiophenol
T6657 231-238 CHEBI:60004;CHEBI:60004 denotes mixture
T33281 288-295 CHEBI:15377;CHEBI:15377 denotes aqueous
T65041 296-300 CHEBI:32145;CHEBI:32145 denotes NaOH
T40366 301-309 CHEBI:75958;CHEBI:75958 denotes solution
T1989 323-330 CHEBI:15377;CHEBI:15377 denotes aqueous
T99804 441-447 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T52387 536-542 CHEBI:30563;CHEBI:30563 denotes silica
T84377 570-574 CHEBI:32145;CHEBI:32145 denotes MeOH
T32932 654-658 CHEBI:32145;CHEBI:32145 denotes MeOH
T16692 682-687 CHEBI:30808;CHEBI:30808 denotes CDCl3
T39500 1121-1124 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
676 62-65 Chemical denotes DMF
677 84-89 Chemical denotes K2CO3 MESH:C037593
678 122-132 Chemical denotes thiophenol MESH:C042983
679 211-216 Chemical denotes argon MESH:D001128
680 256-259 Chemical denotes DCM
681 296-300 Chemical denotes NaOH
682 356-359 Chemical denotes DCM
683 423-428 Chemical denotes brine MESH:C017082
684 441-447 Chemical denotes Na2SO4
685 536-546 Chemical denotes silica gel MESH:D058428
686 570-574 Chemical denotes MeOH
687 578-581 Chemical denotes DCM
688 654-658 Chemical denotes MeOH
689 659-662 Chemical denotes DCM
690 1379-1393 Chemical denotes C37H62N11O7Si2
691 1352-1356 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T286 3-4 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T287 134-136 http://purl.obolibrary.org/obo/CLO_0053733 denotes 11
T288 389-396 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T289 389-396 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T290 625-626 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T291 1395-1398 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T673 5-13 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T674 62-65 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T675 84-89 Chemical denotes K2CO3 http://purl.obolibrary.org/obo/CHEBI_131526
T676 122-132 Chemical denotes thiophenol http://purl.obolibrary.org/obo/CHEBI_48498
T677 211-216 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T678 231-238 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T679 256-259 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T680 296-300 Chemical denotes NaOH http://purl.obolibrary.org/obo/CHEBI_32145
T681 301-309 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T682 356-359 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T683 441-447 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T684 536-542 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T685 570-574 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T686 578-581 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T687 640-642 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T688 654-658 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T689 659-662 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T690 665-667 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T691 682-687 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T692 700-702 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T693 714-716 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T694 728-730 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T695 742-744 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T696 787-789 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T697 826-828 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T698 845-847 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T699 864-866 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T700 922-924 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T701 962-964 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T702 1002-1004 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T703 1139-1144 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T7 256-259 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T8 356-359 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T9 578-581 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T10 659-662 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T288 0-161 Sentence denotes To a solution of 19 (210 mg, 0.20 mmol, 1.00 eq) in anhydrous DMF (10 mL) was added K2CO3 (85 mg, 0.61 mmol, 3.00 eq) and thiophenol (11 μL, 1.14 mmol, 5.70 eq).
T289 162-318 Sentence denotes After stirring for 2 h at room temperature under argon, the reaction mixture was diluted with DCM (20 mL) and washed with 1 M aqueous NaOH solution (10 mL).
T290 319-478 Sentence denotes The aqueous layer was extracted with DCM (3 × 20 mL) and the combined organic extracts were washed with brine, dried over Na2SO4 and concentrated under vacuum.
T291 479-639 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–15% MeOH in DCM) as the eluent to give 20 (129 mg, 76%) as a white solid.
T292 640-664 Sentence denotes Rf 0.31 (8:92 MeOH/DCM).
T293 665-1120 Sentence denotes 1H NMR (500 MHz, CDCl3) δ 8.32 (s, 1H), 8.31 (s, 1H), 8.17 (s, 1H), 7.93 (s, 1H), 6.17–6.06 (m, 5H), 6.03 (d, J = 2.9 Hz, 1H), 5.39 (dd, J = 6.5 Hz, J = 3.0 Hz, 1H), 4.99–4.92 (m, 1H), 4.51–4.45 (m, 1H), 4.33–4.25 (m, 2H), 4.08 (dt, J = 5.6 Hz, J = 3.2 Hz, 1H), 3.98 (dd, J = 11.5 Hz, J = 3.6 Hz, 1H), 3.75 (dd, J = 11.6 Hz, J = 2.8 Hz, 1H), 3.71–3.63 (m, 2H), 2.95–2.69 (m, 4H), 1.61 (s, 3H), 1.37 (s, 3H), 0.92 (s, 9H), 0.88 (s, 9H), 0.13–0.04 (m, 12H).
T294 1121-1351 Sentence denotes 13C NMR (125 MHz, CDCl3) δ 155.8, 155.7, 153.3, 153.1, 149.7, 149.6, 139.8, 139.4, 120.5, 120.3, 114.8, 90.7, 87.2, 85.8, 85.1, 83.9, 82.6, 82.4, 70.3, 70.13, 62.0, 51.5, 49.5, 27.4, 26.2, 25.8, 18.6, 18.2, −4.5, −4.8, −5.2, −5.3.
T295 1352-1401 Sentence denotes HRMS (ESI+): m/z calcd for C37H62N11O7Si2 [M+H]+:
T296 1402-1418 Sentence denotes 828.4372, found:
T297 1419-1428 Sentence denotes 828.4371.