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PMC:7291971 / 75226-77165 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T1493 50-69 CHEBI:53233;CHEBI:53233 denotes dimethyl-tetrahydro
T1494 70-72 CHEBI:53233;CHEBI:53233 denotes 2H
T1495 77-80 CHEBI:53233;CHEBI:53233 denotes [3,
T1496 81-82 CHEBI:53233;CHEBI:53233 denotes -
T1497 86-87 CHEBI:53233;CHEBI:53233 denotes 1
T1498 87-89 CHEBI:52029;CHEBI:52029 denotes ,3
T1499 89-102 CHEBI:53233;CHEBI:53233 denotes ]dioxol-4-yl]
T1500 159-160 CHEBI:53233;CHEBI:53233 denotes -
T1501 160-178 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T1502 179-182 CHEBI:29354;CHEBI:29354 denotes oxy
T1503 183-187 CHEBI:53233;CHEBI:53233 denotes -5-{
T1504 188-194 CHEBI:53233;CHEBI:53233 denotes (tert-
T1505 194-212 CHEBI:8502;CHEBI:8502 denotes butyldimethylsilyl
T1506 212-213 CHEBI:53233;CHEBI:53233 denotes )
T1507 213-216 CHEBI:29354;CHEBI:29354 denotes oxy
T1508 217-223 CHEBI:16625;CHEBI:16625 denotes methyl
T1509 224-236 CHEBI:53233;CHEBI:53233 denotes oxolan-3-yl]
T1510 236-239 CHEBI:15533;CHEBI:15533 denotes oxy
T1511 247-249 CHEBI:86228;CHEBI:86228 denotes 4-
T1512 249-262 CHEBI:23132;CHEBI:23132 denotes chlorobenzene
T1513 262-265 CHEBI:28714;CHEBI:28714 denotes -1-
T1514 265-276 CHEBI:35358;CHEBI:35358 denotes sulfonamide
T1515 287-295 CHEBI:75958;CHEBI:75958 denotes solution
T1516 399-400 CHEBI:75508;CHEBI:75508 denotes 4
T1517 400-422 CHEBI:86228;CHEBI:86228 denotes -chlorobenzenesulfonyl
T1518 423-431 CHEBI:17996;CHEBI:17996 denotes chloride
T1519 495-502 CHEBI:60004;CHEBI:60004 denotes mixture
T1520 556-564 CHEBI:46787;CHEBI:46787 denotes Solvents
T1521 662-669 CHEBI:15377;CHEBI:15377 denotes aqueous
T1522 670-676 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T1523 690-697 CHEBI:15377;CHEBI:15377 denotes aqueous
T1524 816-822 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T1525 911-917 CHEBI:30563;CHEBI:30563 denotes silica
T1526 944-948 CHEBI:32145;CHEBI:32145 denotes MeOH
T1527 1015-1019 CHEBI:32145;CHEBI:32145 denotes MeOH
T1528 1046-1051 CHEBI:30808;CHEBI:30808 denotes CDCl3
T1529 1602-1605 CHEBI:36927;CHEBI:36927 denotes 13C
T84702 50-69 CHEBI:53233;CHEBI:53233 denotes dimethyl-tetrahydro
T58979 70-72 CHEBI:53233;CHEBI:53233 denotes 2H
T83384 77-80 CHEBI:53233;CHEBI:53233 denotes [3,
T81396 81-82 CHEBI:53233;CHEBI:53233 denotes -
T35056 86-87 CHEBI:53233;CHEBI:53233 denotes 1
T57925 87-89 CHEBI:52029;CHEBI:52029 denotes ,3
T25773 89-102 CHEBI:53233;CHEBI:53233 denotes ]dioxol-4-yl]
T78363 159-160 CHEBI:53233;CHEBI:53233 denotes -
T98012 160-178 CHEBI:28714;CHEBI:28714 denotes butyldimethylsilyl
T78667 179-182 CHEBI:29354;CHEBI:29354 denotes oxy
T30177 183-187 CHEBI:53233;CHEBI:53233 denotes -5-{
T65451 188-194 CHEBI:53233;CHEBI:53233 denotes (tert-
T67515 194-212 CHEBI:8502;CHEBI:8502 denotes butyldimethylsilyl
T38465 212-213 CHEBI:53233;CHEBI:53233 denotes )
T95614 213-216 CHEBI:29354;CHEBI:29354 denotes oxy
T12953 217-223 CHEBI:16625;CHEBI:16625 denotes methyl
T31857 224-236 CHEBI:53233;CHEBI:53233 denotes oxolan-3-yl]
T23130 236-239 CHEBI:15533;CHEBI:15533 denotes oxy
T29433 247-249 CHEBI:86228;CHEBI:86228 denotes 4-
T48427 249-262 CHEBI:23132;CHEBI:23132 denotes chlorobenzene
T20740 262-265 CHEBI:28714;CHEBI:28714 denotes -1-
T83097 265-276 CHEBI:35358;CHEBI:35358 denotes sulfonamide
T36071 287-295 CHEBI:75958;CHEBI:75958 denotes solution
T61117 399-400 CHEBI:75508;CHEBI:75508 denotes 4
T43640 400-422 CHEBI:86228;CHEBI:86228 denotes -chlorobenzenesulfonyl
T85525 423-431 CHEBI:17996;CHEBI:17996 denotes chloride
T10406 495-502 CHEBI:60004;CHEBI:60004 denotes mixture
T86047 556-564 CHEBI:46787;CHEBI:46787 denotes Solvents
T70835 662-669 CHEBI:15377;CHEBI:15377 denotes aqueous
T37082 670-676 CHEBI:32139;CHEBI:32139 denotes NaHCO3
T2244 690-697 CHEBI:15377;CHEBI:15377 denotes aqueous
T82981 816-822 CHEBI:34683;CHEBI:34683 denotes Na2SO4
T6219 911-917 CHEBI:30563;CHEBI:30563 denotes silica
T88827 944-948 CHEBI:32145;CHEBI:32145 denotes MeOH
T83956 1015-1019 CHEBI:32145;CHEBI:32145 denotes MeOH
T11227 1046-1051 CHEBI:30808;CHEBI:30808 denotes CDCl3
T70724 1602-1605 CHEBI:36927;CHEBI:36927 denotes 13C

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
1404 344-347 Chemical denotes DCM
1405 365-369 Chemical denotes Et3N
1406 399-431 Chemical denotes 4-chlorobenzenesulfonyl chloride
1407 549-554 Chemical denotes argon MESH:D001128
1408 624-627 Chemical denotes DCM
1409 670-676 Chemical denotes NaHCO3 MESH:D017693
1410 723-726 Chemical denotes DCM
1411 790-795 Chemical denotes brine MESH:C017082
1412 816-822 Chemical denotes Na2SO4
1413 911-921 Chemical denotes silica gel MESH:D058428
1414 944-948 Chemical denotes MeOH
1415 952-955 Chemical denotes DCM
1416 1015-1019 Chemical denotes MeOH
1417 1020-1026 Chemical denotes CH2Cl2
1418 1885-1902 Chemical denotes C43H65N11O9SSi2Cl
1419 1858-1862 Disease denotes HRMS

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T404 278-280 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34
T405 285-286 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T406 756-763 http://purl.obolibrary.org/obo/OBI_0100026 denotes organic
T407 756-763 http://purl.obolibrary.org/obo/UBERON_0000468 denotes organic
T408 965-967 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34
T409 985-986 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T410 1904-1907 http://purl.obolibrary.org/obo/CLO_0007706 denotes M+H

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T35779 23-44 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T95569 25-30 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T55421 50-58 Chemical denotes dimethyl http://purl.obolibrary.org/obo/CHEBI_33601|http://purl.obolibrary.org/obo/CHEBI_42266
T35755 102-108 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T60423 128-149 Chemical denotes 6-amino-9H-purin-9-yl http://purl.obolibrary.org/obo/CHEBI_30756
T29079 130-135 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T95003 179-182 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T91402 213-216 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T56772 217-223 Chemical denotes methyl http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309
T25632 236-239 Chemical denotes oxy http://purl.obolibrary.org/obo/CHEBI_29354
T92641 240-245 Chemical denotes ethyl http://purl.obolibrary.org/obo/CHEBI_37807|http://purl.obolibrary.org/obo/CHEBI_62801
T56172 249-262 Chemical denotes chlorobenzene http://purl.obolibrary.org/obo/CHEBI_28097
T79394 265-276 Chemical denotes sulfonamide http://purl.obolibrary.org/obo/CHEBI_35358
T39178 287-295 Chemical denotes solution http://purl.obolibrary.org/obo/CHEBI_75958
T7288 344-347 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T21825 423-431 Chemical denotes chloride http://purl.obolibrary.org/obo/CHEBI_17996
T39091 495-502 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T12679 549-554 Chemical denotes argon http://purl.obolibrary.org/obo/CHEBI_49475
T62923 624-627 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T78174 670-676 Chemical denotes NaHCO3 http://purl.obolibrary.org/obo/CHEBI_32139
T56606 723-726 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T38211 816-822 Chemical denotes Na2SO4 http://purl.obolibrary.org/obo/CHEBI_32149
T55386 911-917 Chemical denotes silica http://purl.obolibrary.org/obo/CHEBI_30563
T95902 944-948 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T64508 952-955 Chemical denotes DCM http://purl.obolibrary.org/obo/CHEBI_15767
T23226 1000-1002 Chemical denotes Rf http://purl.obolibrary.org/obo/CHEBI_33346
T19017 1015-1019 Chemical denotes MeOH http://purl.obolibrary.org/obo/CHEBI_17790
T17814 1029-1031 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T95988 1046-1051 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365
T72152 1064-1066 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T724 1078-1080 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43471 1092-1094 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T34939 1106-1108 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T727 1170-1172 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T50503 1228-1230 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T2649 1267-1269 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T28528 1306-1308 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T10272 1325-1327 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T66248 1364-1366 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T43013 1403-1405 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T35561 1443-1445 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T70756 1502-1504 Chemical denotes 1H http://purl.obolibrary.org/obo/CHEBI_49637
T3928 1620-1625 Chemical denotes CDCl3 http://purl.obolibrary.org/obo/CHEBI_85365

LitCovid-PD-HP

Id Subject Object Predicate Lexical cue hp_id
T29 344-347 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T30 624-627 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T31 723-726 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644
T32 952-955 Phenotype denotes DCM http://purl.obolibrary.org/obo/HP_0001644

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T504 0-281 Sentence denotes 4.1.34 N-{[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}-N-(2-{[(2R,5R)-2-(6-amino-9H-purin-9-yl)-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-3-yl]oxy}ethyl)-4-chlorobenzene-1-sulfonamide (34)
T505 282-398 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 399-555 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 556-685 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 686-853 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 854-999 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 1000-1028 Sentence denotes Rf 0.67 (10:90 MeOH/CH2Cl2).
T511 1029-1601 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 1602-1857 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 1858-1910 Sentence denotes HRMS (ESI+): m/z calcd for C43H65N11O9SSi2Cl [M+H]+:
T514 1911-1928 Sentence denotes 1002.3909, found:
T515 1929-1939 Sentence denotes 1002.3928.