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PMC:7291971 / 62135-63555 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T1251 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T1252 17-18 CHEBI:34018;CHEBI:34018 denotes 5
T1253 18-19 CHEBI:53250;CHEBI:53250 denotes ′
T1254 19-20 CHEBI:75508;CHEBI:75508 denotes -
T1255 20-25 CHEBI:46882;CHEBI:46882 denotes amino
T1256 25-26 CHEBI:75508;CHEBI:75508 denotes -
T1257 26-46 CHEBI:53250;CHEBI:53250 denotes 2′,3′-isopropylidene
T1258 47-56 CHEBI:22260;CHEBI:22260 denotes adenosine
T1259 157-159 CHEBI:86228;CHEBI:86228 denotes 2-
T1260 159-164 CHEBI:29785;CHEBI:29785 denotes nitro
T1261 164-196 CHEBI:86228;CHEBI:86228 denotes -4-trifluoromethylbenzenesufonyl
T1262 197-205 CHEBI:17996;CHEBI:17996 denotes chloride
T1263 270-277 CHEBI:60004;CHEBI:60004 denotes mixture
T1264 324-329 CHEBI:2511;CHEBI:2511 denotes argon
T1265 344-351 CHEBI:60004;CHEBI:60004 denotes mixture
T1266 387-392 CHEBI:15377;CHEBI:15377 denotes water
T1267 406-413 CHEBI:15377;CHEBI:15377 denotes aqueous
T1268 534-540 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T1269 629-635 CHEBI:30563;CHEBI:30563 denotes silica
T1270 662-666 CHEBI:32145;CHEBI:32145 denotes MeOH
T1271 735-739 CHEBI:32145;CHEBI:32145 denotes MeOH
T1272 1127-1130 CHEBI:36927;CHEBI:36927 denotes 13C
T26922 5-13 CHEBI:75958;CHEBI:75958 denotes solution
T37045 17-18 CHEBI:34018;CHEBI:34018 denotes 5
T78171 18-19 CHEBI:53250;CHEBI:53250 denotes ′
T33253 19-20 CHEBI:75508;CHEBI:75508 denotes -
T52510 20-25 CHEBI:46882;CHEBI:46882 denotes amino
T10078 25-26 CHEBI:75508;CHEBI:75508 denotes -
T92577 26-46 CHEBI:53250;CHEBI:53250 denotes 2′,3′-isopropylidene
T98848 47-56 CHEBI:22260;CHEBI:22260 denotes adenosine
T6780 157-159 CHEBI:86228;CHEBI:86228 denotes 2-
T90464 159-164 CHEBI:29785;CHEBI:29785 denotes nitro
T13282 164-196 CHEBI:86228;CHEBI:86228 denotes -4-trifluoromethylbenzenesufonyl
T47375 197-205 CHEBI:17996;CHEBI:17996 denotes chloride
T91473 270-277 CHEBI:60004;CHEBI:60004 denotes mixture
T29148 324-329 CHEBI:2511;CHEBI:2511 denotes argon
T37167 344-351 CHEBI:60004;CHEBI:60004 denotes mixture
T88824 387-392 CHEBI:15377;CHEBI:15377 denotes water
T70018 406-413 CHEBI:15377;CHEBI:15377 denotes aqueous
T75778 534-540 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T42939 629-635 CHEBI:30563;CHEBI:30563 denotes silica
T97301 662-666 CHEBI:32145;CHEBI:32145 denotes MeOH
T5962 735-739 CHEBI:32145;CHEBI:32145 denotes MeOH
T51133 1127-1130 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1118 17-46 Chemical denotes 5′-amino-2′,3′-isopropylidene
1119 47-56 Chemical denotes adenosine MESH:D000241
1120 99-102 Chemical denotes DMF
1121 122-126 Chemical denotes Et3N
1122 157-205 Chemical denotes 2-nitro-4-trifluoromethylbenzenesufonyl chloride
1123 324-329 Chemical denotes argon MESH:D001128
1124 387-392 Chemical denotes water MESH:D014867
1125 534-540 Chemical denotes Na2SO4
1126 629-639 Chemical denotes silica gel MESH:D058428
1127 662-666 Chemical denotes MeOH
1128 670-673 Chemical denotes DCM
1129 735-739 Chemical denotes MeOH
1130 740-746 Chemical denotes CH2Cl2
1131 749-751 Chemical denotes 1H
1132 766-772 Chemical denotes DMSO‑d
1133 799-801 Chemical denotes 1H
1134 825-827 Chemical denotes 1H
1135 839-841 Chemical denotes 1H
1136 853-855 Chemical denotes 1H
1137 892-894 Chemical denotes 1H
1138 1373-1386 Chemical denotes C20H21N7O7SF3
1139 1346-1350 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T363 3-4 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T364 474-481 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T365 474-481 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T366 695-697 http://purl.obolibrary.org/obo/CLO_0053799 denotes 45
T367 703-704 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T368 1388-1391 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T334 5-13 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T49996 20-25 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T336 32-46 Chemical denotes isopropylidene http://purl.obolibrary.org/obo/CHEBI_29858
T66989 47-56 Chemical denotes adenosine http://purl.obolibrary.org/obo/CHEBI_16335
T98465 99-102 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T54606 159-164 Chemical denotes nitro http://purl.obolibrary.org/obo/CHEBI_29785
T80254 197-205 Chemical denotes chloride http://purl.obolibrary.org/obo/CHEBI_17996
T51701 270-277 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T342 324-329 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T48319 344-351 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T60107 369-374 Chemical denotes AcOEt http://purl.obolibrary.org/obo/CHEBI_27750
T59374 387-392 Chemical denotes water http://purl.obolibrary.org/obo/CHEBI_15377
T52962 439-444 Chemical denotes AcOEt http://purl.obolibrary.org/obo/CHEBI_27750
T23043 534-540 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T348 629-635 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T33545 662-666 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T55497 670-673 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T10772 721-723 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T48310 735-739 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T39153 749-751 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T64417 766-770 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262
T67452 799-801 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2039 825-827 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T357 839-841 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T60176 853-855 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T32588 892-894 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70644 958-960 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T37735 997-999 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T51184 1036-1038 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T71680 1075-1077 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T5000 1145-1149 Chemical denotes DMSO http://purl.obolibrary.org/obo/CHEBI_28262

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T24 670-673 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T430 0-156 Sentence denotes To a solution of 5′-amino-2′,3′-isopropylidene adenosine (280 mg, 0.92 mmol, 1.00 eq) in anhydrous DMF (4.6 mL) was added Et3N (250 μL, 1.83 mmol, 2.00 eq).
T431 157-330 Sentence denotes 2-nitro-4-trifluoromethylbenzenesufonyl chloride (396 mg, 1.37 mmol, 1.50 eq) was added at 0 °C and the reaction mixture was stirred for 4 h at room temperature under argon.
T432 331-401 Sentence denotes The reaction mixture was diluted with AcOEt (30 mL) and water (30 mL).
T433 402-571 Sentence denotes The aqueous layer was extracted with AcOEt (3 × 30 mL) and the combined organic extracts were washed with brine (30 mL), dried over Na2SO4 and concentrated under vacuum.
T434 572-720 Sentence denotes The residue was purified by flash column chromatography (silica gel, linear gradient 0–5% MeOH in DCM) to give 28 (230 mg, 45%) as a dark red solid.
T435 721-748 Sentence denotes Rf 0.34 (8:92 MeOH/CH2Cl2).
T436 749-1126 Sentence denotes 1H NMR (500 MHz, DMSO‑d 6) δ 8.93 (t, J = 5.1 Hz, 1H), 8.50 (d, J = 1.8 Hz, 1H), 8.28 (s, 1H), 8.14 (s, 1H), 8.10 (dd, J = 1.6 Hz, J = 8.6 Hz, 1H), 8.04 (d, J = 8.3 Hz), 7.45 (br. s, 2H), 6.11 (d, J = 2.9 Hz, 1H), 5.34 (dd, J = 6.3 Hz, J = 2.9 Hz, 1H), 4.92 (dd, J = 6.3 Hz, J = 3.1 Hz, 1H), 4.20 (td, J = 5.9 Hz, J = 3.1 Hz, 1H), 3.37–3.25 (m, 2H), 1.50 (s, 3H), 1.27 (s, 3H).
T437 1127-1345 Sentence denotes 13C NMR (125 MHz, DMSO‑d 6) δ 156.1, 152.4, 148.4, 147.6, 140.2, 136.4, 133.8, 133.5, 133.2, 133.0, 130.8, 129.4, 125.5, 123.4, 121.2, 119.0, 122.0, 122.0, 119.3, 113.5, 107.7, 89.4, 84.3, 83.0, 81.5, 44.7, 26.9, 25.0.
T438 1346-1394 Sentence denotes HRMS (ESI+): m/z calcd for C20H21N7O7SF3 [M+H]+:
T439 1395-1420 Sentence denotes 560.1175, Found 560.1180.