PMC:7571312 / 48510-50113
Annnotations
LitCovid-PD-FMA-UBERON
Id | Subject | Object | Predicate | Lexical cue | fma_id |
---|---|---|---|---|---|
T93 | 491-494 | Body_part | denotes | CsF | http://purl.org/sig/ont/fma/fma20935 |
LitCovid-PD-CLO
Id | Subject | Object | Predicate | Lexical cue |
---|---|---|---|---|
T459 | 161-162 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
T460 | 201-203 | http://purl.obolibrary.org/obo/CLO_0050509 | denotes | 27 |
T461 | 231-232 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
T462 | 528-529 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
T463 | 576-577 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
T464 | 747-754 | http://purl.obolibrary.org/obo/OBI_0100026 | denotes | organic |
T465 | 747-754 | http://purl.obolibrary.org/obo/UBERON_0000468 | denotes | organic |
T466 | 942-944 | http://purl.obolibrary.org/obo/CLO_0053799 | denotes | 45 |
T467 | 972-973 | http://purl.obolibrary.org/obo/CLO_0001020 | denotes | a |
T468 | 1458-1460 | http://purl.obolibrary.org/obo/CLO_0007874 | denotes | MS |
T469 | 1493-1498 | http://purl.obolibrary.org/obo/CLO_0007706 | denotes | M + H |
LitCovid-PD-CHEBI
Id | Subject | Object | Predicate | Lexical cue | chebi_id |
---|---|---|---|---|---|
T946 | 23-36 | Chemical | denotes | 1H-indol-2-yl | http://purl.obolibrary.org/obo/CHEBI_51611 |
T947 | 23-25 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T948 | 37-45 | Chemical | denotes | carbonyl | http://purl.obolibrary.org/obo/CHEBI_23019 |
T949 | 49-55 | Chemical | denotes | leucyl | http://purl.obolibrary.org/obo/CHEBI_32630|http://purl.obolibrary.org/obo/CHEBI_37904 |
T951 | 56-61 | Chemical | denotes | amino | http://purl.obolibrary.org/obo/CHEBI_46882 |
T952 | 65-68 | Chemical | denotes | oxo | http://purl.obolibrary.org/obo/CHEBI_46629 |
T953 | 98-103 | Chemical | denotes | butyl | http://purl.obolibrary.org/obo/CHEBI_41264 |
T46839 | 188-199 | Chemical | denotes | acetic acid | http://purl.obolibrary.org/obo/CHEBI_15366 |
T30029 | 195-199 | Chemical | denotes | acid | http://purl.obolibrary.org/obo/CHEBI_37527 |
T40022 | 233-241 | Chemical | denotes | solution | http://purl.obolibrary.org/obo/CHEBI_75958 |
T92548 | 265-271 | Chemical | denotes | chloro | http://purl.obolibrary.org/obo/CHEBI_47853 |
T77046 | 274-277 | Chemical | denotes | oxo | http://purl.obolibrary.org/obo/CHEBI_46629 |
T322 | 308-314 | Chemical | denotes | methyl | http://purl.obolibrary.org/obo/CHEBI_32875|http://purl.obolibrary.org/obo/CHEBI_29309 |
T8 | 315-321 | Chemical | denotes | propyl | http://purl.obolibrary.org/obo/CHEBI_26308 |
T1448 | 322-327 | Chemical | denotes | amino | http://purl.obolibrary.org/obo/CHEBI_46882 |
T89400 | 328-336 | Chemical | denotes | carbonyl | http://purl.obolibrary.org/obo/CHEBI_23019 |
T86029 | 338-351 | Chemical | denotes | 3-methylbutyl | http://purl.obolibrary.org/obo/CHEBI_30359 |
T74561 | 355-362 | Chemical | denotes | methoxy | http://purl.obolibrary.org/obo/CHEBI_32772|http://purl.obolibrary.org/obo/CHEBI_44520 |
T65219 | 363-372 | Chemical | denotes | 1H-indole | http://purl.obolibrary.org/obo/CHEBI_16881 |
T44034 | 363-365 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T41687 | 366-372 | Chemical | denotes | indole | http://purl.obolibrary.org/obo/CHEBI_35581 |
T75707 | 375-386 | Chemical | denotes | carboxamide | http://purl.obolibrary.org/obo/CHEBI_23004|http://purl.obolibrary.org/obo/CHEBI_37622 |
T19 | 410-413 | Chemical | denotes | DMF | http://purl.obolibrary.org/obo/CHEBI_17741 |
T75923 | 439-441 | Chemical | denotes | N2 | http://purl.obolibrary.org/obo/CHEBI_17997 |
T30381 | 460-468 | Chemical | denotes | solution | http://purl.obolibrary.org/obo/CHEBI_75958 |
T8447 | 530-536 | Chemical | denotes | Teflon | http://purl.obolibrary.org/obo/CHEBI_53251 |
T16308 | 672-677 | Chemical | denotes | water | http://purl.obolibrary.org/obo/CHEBI_15377 |
T44169 | 706-721 | Chemical | denotes | dichloromethane | http://purl.obolibrary.org/obo/CHEBI_15767 |
T72291 | 779-784 | Chemical | denotes | water | http://purl.obolibrary.org/obo/CHEBI_15377 |
T52737 | 899-907 | Chemical | denotes | methanol | http://purl.obolibrary.org/obo/CHEBI_17790 |
T27 | 908-923 | Chemical | denotes | dichloromethane | http://purl.obolibrary.org/obo/CHEBI_15767 |
T47188 | 987-989 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T21947 | 1004-1008 | Chemical | denotes | DMSO | http://purl.obolibrary.org/obo/CHEBI_28262 |
T62313 | 1025-1027 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T65167 | 1051-1053 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T7414 | 1077-1079 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T29594 | 1091-1093 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T13853 | 1117-1119 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T11215 | 1143-1145 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T84447 | 1169-1171 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T75855 | 1195-1197 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T35764 | 1221-1223 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T55887 | 1240-1242 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T7116 | 1311-1313 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T12321 | 1330-1332 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T67952 | 1363-1365 | Chemical | denotes | 1H | http://purl.obolibrary.org/obo/CHEBI_49637 |
T77336 | 1458-1460 | Chemical | denotes | MS | http://purl.obolibrary.org/obo/CHEBI_73613 |
T73211 | 1534-1537 | Chemical | denotes | H2O | http://purl.obolibrary.org/obo/CHEBI_15377 |
LitCovid-sentences
Id | Subject | Object | Predicate | Lexical cue |
---|---|---|---|---|
T320 | 0-116 | Sentence | denotes | (3S)-3-({N-[(4-Methoxy-1H-indol-2-yl)carbonyl]-l-leucyl}amino)-2-oxo-4-[(3S)-2-oxopyrrolidin-3-yl]butyl Acetate (13) |
T321 | 117-442 | Sentence | denotes | An oven-dried 40 mL scintillation vial with a spinbar was charged with acetic acid (27 mg, 0.46 mmol) followed by a solution of N-((1S)-1-{[((1S)-3-chloro-2-oxo-1-{[(3S)-2-oxopyrrolidin-3-yl]methyl}propyl)amino]carbonyl}-3-methylbutyl)-4-methoxy-1H-indole-2-carboxamide (172 mg, 0.35 mmol) in DMF (3.5 mL) and purged with N2. |
T322 | 443-616 | Sentence | denotes | This pale yellow solution was then treated with CsF (122 mg, 0.81 mmol), sealed with a Teflon-lined screwcap, and heated at 65 °C on a reaction block with vigorous stirring. |
T323 | 617-733 | Sentence | denotes | After 3 h, the reaction was cooled to RT, diluted with water (30 mL), and extracted with dichloromethane (4 × 7 mL). |
T324 | 734-839 | Sentence | denotes | The combined organic layers were washed with water (2 × 20 mL), brine (20 mL), and concentrated in vacuo. |
T325 | 840-986 | Sentence | denotes | This material was purified by Biotage MPLC (25 M, 2.5–4.5% methanol/dichloromethane) to afford 78 mg (45%) of the title compound as a white solid. |
T326 | 987-1501 | Sentence | denotes | 1H NMR (400 MHz, DMSO-d6) δ 11.57 (s, 1H), 8.57 (d, J = 7.8 Hz, 1H), 8.43 (d, J = 7.6 Hz, 1H), 7.64 (s, 1H), 7.36 (d, J = 1.8 Hz, 1H), 7.08 (t, J = 8.0 Hz, 1H), 6.99 (d, J = 8.1 Hz, 1H), 6.49 (d, J = 7.6 Hz, 1H), 4.83 (d, J = 3.0 Hz, 1H), 4.76–4.95 (m, 1H), 4.35–4.50 (m, 2H), 3.87 (s, 3H), 3.03–3.17 (m, 2H), 2.22–2.35 (m, 1H), 2.09–2.22 (m, 1H), 2.07 (s, 3H), 1.90–2.04 (m, 1H), 1.65–1.77 (m, 2H), 1.48–1.65 (m, 3H), 0.94 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.3 Hz, 3H); MS (ESI+) for C26H34N4O7m/z 515.2 (M + H)+. |
T327 | 1502-1567 | Sentence | denotes | Anal. calcd for C26H34N4O7·0.65 H2O: C, 59.34; H, 6.76; N, 10.65. |
T328 | 1568-1603 | Sentence | denotes | Found: C, 59.41; H, 6.63; N, 10.68. |
LitCovid-PubTator
Id | Subject | Object | Predicate | Lexical cue | tao:has_database_id |
---|---|---|---|---|---|
1142 | 672-677 | Chemical | denotes | water | MESH:D014867 |
1143 | 706-721 | Chemical | denotes | dichloromethane | MESH:D008752 |
1144 | 779-784 | Chemical | denotes | water | MESH:D014867 |
1145 | 798-803 | Chemical | denotes | brine | MESH:C017082 |
1146 | 899-907 | Chemical | denotes | methanol | MESH:D000432 |
1147 | 908-923 | Chemical | denotes | dichloromethane | MESH:D008752 |
1148 | 1518-1528 | Chemical | denotes | C26H34N4O7 | |
1149 | 1534-1537 | Chemical | denotes | H2O | |
1150 | 1539-1540 | Chemical | denotes | C | MESH:D002244 |
1151 | 1558-1559 | Chemical | denotes | N | MESH:D009584 |
1152 | 1575-1576 | Chemical | denotes | C | MESH:D002244 |
1153 | 1594-1595 | Chemical | denotes | N | MESH:D009584 |