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PMC:7291971 / 75508-77165 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T1515 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T1516 117-118 CHEBI:75508;CHEBI:75508 denotes 4
T1517 118-140 CHEBI:86228;CHEBI:86228 denotes -chlorobenzenesulfonyl
T1518 141-149 CHEBI:17996;CHEBI:17996 denotes chloride
T1519 213-220 CHEBI:60004;CHEBI:60004 denotes mixture
T1520 274-282 CHEBI:46787;CHEBI:46787 denotes Solvents
T1521 380-387 CHEBI:15377;CHEBI:15377 denotes aqueous
T1522 388-394 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T1523 408-415 CHEBI:15377;CHEBI:15377 denotes aqueous
T1524 534-540 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T1525 629-635 CHEBI:30563;CHEBI:30563 denotes silica
T1526 662-666 CHEBI:32145;CHEBI:32145 denotes MeOH
T1527 733-737 CHEBI:32145;CHEBI:32145 denotes MeOH
T1528 764-769 CHEBI:30808;CHEBI:30808 denotes CDCl3
T1529 1320-1323 CHEBI:36927;CHEBI:36927 denotes 13C
T36071 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T61117 117-118 CHEBI:75508;CHEBI:75508 denotes 4
T43640 118-140 CHEBI:86228;CHEBI:86228 denotes -chlorobenzenesulfonyl
T85525 141-149 CHEBI:17996;CHEBI:17996 denotes chloride
T10406 213-220 CHEBI:60004;CHEBI:60004 denotes mixture
T86047 274-282 CHEBI:46787;CHEBI:46787 denotes Solvents
T70835 380-387 CHEBI:15377;CHEBI:15377 denotes aqueous
T37082 388-394 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T2244 408-415 CHEBI:15377;CHEBI:15377 denotes aqueous
T82981 534-540 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T6219 629-635 CHEBI:30563;CHEBI:30563 denotes silica
T88827 662-666 CHEBI:32145;CHEBI:32145 denotes MeOH
T83956 733-737 CHEBI:32145;CHEBI:32145 denotes MeOH
T11227 764-769 CHEBI:30808;CHEBI:30808 denotes CDCl3
T70724 1320-1323 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1404 62-65 Chemical denotes DCM
1405 83-87 Chemical denotes Et3N
1406 117-149 Chemical denotes 4-chlorobenzenesulfonyl chloride
1407 267-272 Chemical denotes argon MESH:D001128
1408 342-345 Chemical denotes DCM
1409 388-394 Chemical denotes NaHCO3 MESH:D017693
1410 441-444 Chemical denotes DCM
1411 508-513 Chemical denotes brine MESH:C017082
1412 534-540 Chemical denotes Na2SO4
1413 629-639 Chemical denotes silica gel MESH:D058428
1414 662-666 Chemical denotes MeOH
1415 670-673 Chemical denotes DCM
1416 733-737 Chemical denotes MeOH
1417 738-744 Chemical denotes CH2Cl2
1418 1603-1620 Chemical denotes C43H65N11O9SSi2Cl
1419 1576-1580 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T405 3-4 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T406 474-481 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T407 474-481 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T408 683-685 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34
T409 703-704 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T410 1622-1625 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T39178 5-13 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T7288 62-65 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T21825 141-149 Chemical denotes chloride http://purl.obolibrary.org/obo/CHEBI_17996
T39091 213-220 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T12679 267-272 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T62923 342-345 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T78174 388-394 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T56606 441-444 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T38211 534-540 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T55386 629-635 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T95902 662-666 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T64508 670-673 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T23226 718-720 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T19017 733-737 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T17814 747-749 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95988 764-769 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T72152 782-784 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T724 796-798 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43471 810-812 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T34939 824-826 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T727 888-890 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T50503 946-948 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2649 985-987 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28528 1024-1026 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T10272 1043-1045 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T66248 1082-1084 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43013 1121-1123 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35561 1161-1163 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70756 1220-1222 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T3928 1338-1343 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T29 62-65 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T30 342-345 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T31 441-444 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T32 670-673 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T505 0-116 Sentence denotes To a solution of 20 (171 mg, 0.21 mmol, 1.00 eq) in anhydrous DCM (2 mL) was added Et3N (60 μL, 0.41 mmol, 2.00 eq).
T506 117-273 Sentence denotes 4-chlorobenzenesulfonyl chloride (65 mg, 0.31 mmol, 1.50 eq) was added at 0 °C and the reaction mixture was stirred for 3 h at room temperature under argon.
T507 274-403 Sentence denotes Solvents were removed under vacuum and the residue was diluted with DCM (40 mL) and washed with saturated aqueous NaHCO3 (40 mL).
T508 404-571 Sentence denotes The aqueous layer was extracted with DCM (3 × 30 mL) and the combined organic extracts were washed with brine (30 mL), dried over Na2SO4 and concentrated under vacuum.
T509 572-717 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–4% MeOH in DCM) to give 34 (188 mg, 90%) as a white solid.
T510 718-746 Sentence denotes Rf 0.67 (10:90 MeOH/CH2Cl2).
T511 747-1319 Sentence denotes 1H NMR (500 MHz, CDCl3) δ 8.32 (s, 1H), 8.29 (s, 1H), 8.12 (s, 1H), 7.81 (s, 1H), 7.59–7.46 (m, 2H), 7.34–7.22 (m, 2H), 5.97 (d, J = 3.3 Hz, 1H), 5.96–5.88 (m, 5H), 5.41 (dd, J = 6.4 Hz, J = 2.0 Hz, 1H), 5.07 (dd, J = 6.4 Hz, J = 3.5 Hz, 1H), 4.50 (dd, J = 5.9 Hz, J = 4.6 Hz, 1H), 4.46–4.34 (m, 1H), 4.21 (dd, J = 4.7 Hz, J = 3.3 Hz, 1H), 4.03 (dt, J = 6.0 Hz, J = 3.0 Hz, 1H), 3.98 (dd, J = 11.4 Hz, J = 3.5 Hz, 1H), 3.80–3.72 (m, 3H), 3.68 (dd, J = 14.6 Hz, J = 5.6 Hz, 1H), 3.46–3.31 (m, 3H), 1.57 (s, 3H), 1.36 (s, 3H), 0.91 (s, 9H), 0.89 (s, 9H), 0.11–0.03 (m, 12H).
T512 1320-1575 Sentence denotes 13C NMR (125 MHz, CDCl3) δ 155.8, 155.6, 153.2, 153.1, 149.5, 149.1, 140.2, 139.5, 139.1, 138.0, 129.2, 128.6, 120.5, 120.2, 114.6, 90.9, 87.3, 85.3, 84.5, 84.1, 82.6 (2C), 69.6 (2C), 61.6, 50.7, 48.1, 27.2, 26.1, 25.9, 25.4, 18.6, 18.2, −4.5, −4.7, −5.3.
T513 1576-1628 Sentence denotes HRMS (ESI+): m/z calcd for C43H65N11O9SSi2Cl [M+H]+:
T514 1629-1646 Sentence denotes 1002.3909, found:
T515 1647-1657 Sentence denotes 1002.3928.