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PMC:7291971 / 12321-14381 JSONTXT

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LitCovid-PMC-OGER-BB

Id Subject Object Predicate Lexical cue
T287 195-196 CHEBI:75508;CHEBI:75508 denotes 5
T288 196-197 CHEBI:82321;CHEBI:82321 denotes ′
T289 197-198 CHEBI:50217;CHEBI:50217 denotes -
T290 198-203 CHEBI:46882;CHEBI:46882 denotes amino
T291 203-204 CHEBI:75508;CHEBI:75508 denotes -
T292 204-205 CHEBI:53233;CHEBI:53233 denotes 2
T293 205-206 CHEBI:52029;CHEBI:52029 denotes ′
T294 206-207 CHEBI:75508;CHEBI:75508 denotes ,
T295 207-209 CHEBI:52029;CHEBI:52029 denotes 3′
T296 209-224 CHEBI:53250;CHEBI:53250 denotes -isopropylidene
T297 225-234 CHEBI:22260;CHEBI:22260 denotes adenosine
T298 304-319 CHEBI:32863;CHEBI:32863 denotes secondary amine
T299 420-425 CHEBI:32877;CHEBI:32877 denotes amine
T300 497-511 CHEBI:32877;CHEBI:32877 denotes primary amines
T301 538-562 CHEBI:53325;CHEBI:53325 denotes nitrobenzenesulfonamides
T302 567-573 CHEBI:32988;CHEBI:32988 denotes amides
T303 611-616 CHEBI:24433;CHEBI:24433 denotes group
T304 782-807 CHEBI:86228;CHEBI:86228 denotes 2-nitrobenzenesulfonamide
T305 877-892 GO:0006306 denotes DNA methylation
T306 938-947 CHEBI:22260;CHEBI:22260 denotes adenosine
T307 1139-1161 CHEBI:86228;CHEBI:86228 denotes 4-nitrobenzenesulfonyl
T308 1162-1170 CHEBI:17996;CHEBI:17996 denotes chloride
T309 1209-1231 CHEBI:86228;CHEBI:86228 denotes 2-nitrobenzenesulfonyl
T310 1232-1240 CHEBI:17996;CHEBI:17996 denotes chloride
T311 1268-1269 CHEBI:53233;CHEBI:53233 denotes 5
T312 1269-1270 CHEBI:82321;CHEBI:82321 denotes ′
T313 1270-1271 CHEBI:50217;CHEBI:50217 denotes -
T314 1271-1276 CHEBI:46882;CHEBI:46882 denotes amino
T315 1276-1277 CHEBI:75508;CHEBI:75508 denotes -
T316 1277-1278 CHEBI:53233;CHEBI:53233 denotes 2
T317 1278-1279 CHEBI:52029;CHEBI:52029 denotes ′
T318 1279-1280 CHEBI:53250;CHEBI:53250 denotes ,
T319 1280-1281 CHEBI:52029;CHEBI:52029 denotes 3
T320 1281-1297 CHEBI:53250;CHEBI:53250 denotes ′-isopropylidene
T321 1298-1307 CHEBI:22260;CHEBI:22260 denotes adenosine
T322 1350-1351 MOP:0002369 denotes -
T323 1404-1409 CHEBI:32031;CHEBI:32031 denotes K2CO3
T324 1465-1477 CHEBI:23447;CHEBI:23447 denotes dinucleoside
T325 1613-1620 CHEBI:60004;CHEBI:60004 denotes mixture
T326 1720-1728 CHEBI:29917;CHEBI:29917 denotes thiolate
T327 1760-1765 CHEBI:32863;CHEBI:32863 denotes amine
T328 1801-1818 CHEBI:51087;CHEBI:51087 denotes protecting groups
T329 1844-1850 CHEBI:37527;CHEBI:37527 denotes acidic
T330 1866-1878 CHEBI:23447;CHEBI:23447 denotes dinucleoside
T331 1909-1915 CHEBI:37527;CHEBI:37527 denotes acidic
T332 1984-2009 CHEBI:86228;CHEBI:86228 denotes 4-nitrobenzenesulfonamide

LitCovid-PD-FMA-UBERON

Id Subject Object Predicate Lexical cue fma_id
T52 877-880 Body_part denotes DNA http://purl.org/sig/ont/fma/fma74412
T53 918-926 Body_part denotes cytosine http://purl.org/sig/ont/fma/fma82776
T54 1795-1800 Body_part denotes sugar http://purl.org/sig/ont/fma/fma82737

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
231 35-47 Chemical denotes dinucleoside
232 195-224 Chemical denotes 5′-amino-2′,3′-isopropylidene
233 225-234 Chemical denotes adenosine MESH:D000241
234 252-253 Chemical denotes N MESH:D009584
235 314-319 Chemical denotes amine MESH:D000588
236 420-425 Chemical denotes amine MESH:D000588
237 505-511 Chemical denotes amines MESH:D000588
238 538-562 Chemical denotes nitrobenzenesulfonamides
239 564-573 Chemical denotes Ns-amides
240 782-807 Chemical denotes 2-nitrobenzenesulfonamide
241 918-926 Chemical denotes cytosine MESH:D003596
242 938-947 Chemical denotes adenosine MESH:D000241
243 1025-1034 Chemical denotes adenosine MESH:D000241
244 1052-1064 Chemical denotes dinucleoside
245 1139-1170 Chemical denotes 4-nitrobenzenesulfonyl chloride MESH:C518227
246 1209-1240 Chemical denotes 2-nitrobenzenesulfonyl chloride MESH:C002732
247 1268-1297 Chemical denotes 5′-amino-2′,3′-isopropylidene
248 1298-1307 Chemical denotes adenosine MESH:D000241
249 1365-1373 Chemical denotes Ns-amide
250 1404-1409 Chemical denotes K2CO3 MESH:C037593
251 1413-1416 Chemical denotes DMF
252 1465-1477 Chemical denotes dinucleoside
253 1720-1728 Chemical denotes thiolate
254 1760-1765 Chemical denotes amine MESH:D000588
255 1795-1800 Chemical denotes sugar MESH:D000073893
256 1866-1878 Chemical denotes dinucleoside
257 1958-1966 Chemical denotes Ns-amide
258 1984-2009 Chemical denotes 4-nitrobenzenesulfonamide
259 2021-2033 Chemical denotes dinucleoside

LitCovid-PD-MONDO

Id Subject Object Predicate Lexical cue mondo_id
T33 564-566 Disease denotes Ns http://purl.obolibrary.org/obo/MONDO_0009735
T34 1365-1367 Disease denotes Ns http://purl.obolibrary.org/obo/MONDO_0009735
T35 1958-1960 Disease denotes Ns http://purl.obolibrary.org/obo/MONDO_0009735

LitCovid-PD-CLO

Id Subject Object Predicate Lexical cue
T114 513-514 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T115 583-584 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T116 600-610 http://purl.obolibrary.org/obo/CLO_0001658 denotes activating
T117 617-620 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T118 649-651 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T119 808-811 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T120 1035-1037 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T121 1098-1100 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T122 1172-1174 http://purl.obolibrary.org/obo/CLO_0050507 denotes 22
T123 1181-1184 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T124 1185-1186 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T125 1374-1376 http://purl.obolibrary.org/obo/CLO_0050510 denotes 18
T126 1572-1573 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T127 1705-1706 http://purl.obolibrary.org/obo/CLO_0001020 denotes a
T128 1819-1822 http://purl.obolibrary.org/obo/CLO_0051582 denotes has
T129 2039-2041 http://purl.obolibrary.org/obo/CLO_0001302 denotes 34

LitCovid-PD-CHEBI

Id Subject Object Predicate Lexical cue chebi_id
T206 198-203 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T207 210-224 Chemical denotes isopropylidene http://purl.obolibrary.org/obo/CHEBI_29858
T208 225-234 Chemical denotes adenosine http://purl.obolibrary.org/obo/CHEBI_16335
T209 304-319 Chemical denotes secondary amine http://purl.obolibrary.org/obo/CHEBI_32863
T210 314-319 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T211 412-425 Chemical denotes primary amine http://purl.obolibrary.org/obo/CHEBI_32877
T212 420-425 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T213 497-511 Chemical denotes primary amines http://purl.obolibrary.org/obo/CHEBI_32877
T214 505-511 Chemical denotes amines http://purl.obolibrary.org/obo/CHEBI_32952
T215 564-566 Chemical denotes Ns http://purl.obolibrary.org/obo/CHEBI_33349|http://purl.obolibrary.org/obo/CHEBI_33355
T217 567-573 Chemical denotes amides http://purl.obolibrary.org/obo/CHEBI_32988
T218 611-616 Chemical denotes group http://purl.obolibrary.org/obo/CHEBI_24433
T219 877-880 Chemical denotes DNA http://purl.obolibrary.org/obo/CHEBI_16991
T220 918-926 Chemical denotes cytosine http://purl.obolibrary.org/obo/CHEBI_16040
T221 938-947 Chemical denotes adenosine http://purl.obolibrary.org/obo/CHEBI_16335
T222 1025-1034 Chemical denotes adenosine http://purl.obolibrary.org/obo/CHEBI_16335
T223 1162-1170 Chemical denotes chloride http://purl.obolibrary.org/obo/CHEBI_17996
T224 1232-1240 Chemical denotes chloride http://purl.obolibrary.org/obo/CHEBI_17996
T225 1271-1276 Chemical denotes amino http://purl.obolibrary.org/obo/CHEBI_46882
T226 1283-1297 Chemical denotes isopropylidene http://purl.obolibrary.org/obo/CHEBI_29858
T227 1298-1307 Chemical denotes adenosine http://purl.obolibrary.org/obo/CHEBI_16335
T228 1365-1367 Chemical denotes Ns http://purl.obolibrary.org/obo/CHEBI_33349|http://purl.obolibrary.org/obo/CHEBI_33355
T230 1368-1373 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988
T232 1404-1409 Chemical denotes K2CO3 http://purl.obolibrary.org/obo/CHEBI_131526
T233 1413-1416 Chemical denotes DMF http://purl.obolibrary.org/obo/CHEBI_17741
T234 1594-1596 Chemical denotes KI http://purl.obolibrary.org/obo/CHEBI_74559|http://purl.obolibrary.org/obo/CHEBI_8346
T236 1613-1620 Chemical denotes mixture http://purl.obolibrary.org/obo/CHEBI_60004
T237 1720-1728 Chemical denotes thiolate http://purl.obolibrary.org/obo/CHEBI_50539
T238 1750-1765 Chemical denotes secondary amine http://purl.obolibrary.org/obo/CHEBI_32863
T239 1760-1765 Chemical denotes amine http://purl.obolibrary.org/obo/CHEBI_32952
T240 1958-1960 Chemical denotes Ns http://purl.obolibrary.org/obo/CHEBI_33349|http://purl.obolibrary.org/obo/CHEBI_33355
T242 1961-1966 Chemical denotes amide http://purl.obolibrary.org/obo/CHEBI_29337|http://purl.obolibrary.org/obo/CHEBI_32988

LitCovid-PD-GO-BP

Id Subject Object Predicate Lexical cue
T29 438-449 http://purl.obolibrary.org/obo/GO_0009056 denotes degradation
T30 877-892 http://purl.obolibrary.org/obo/GO_0006306 denotes DNA methylation
T31 881-892 http://purl.obolibrary.org/obo/GO_0032259 denotes methylation

2_test

Id Subject Object Predicate Lexical cue
32563813-21936531-29105576 236-238 21936531 denotes 21
32563813-7086841-29105577 1344-1346 7086841 denotes 23

LitCovid-sentences

Id Subject Object Predicate Lexical cue
T76 0-240 Sentence denotes The retrosynthetic analysis of the dinucleoside 1 structure suggested the coupling reaction between the tosyl derivative 17 previously described by us (Scheme 2) [14], and the readily accessible 5′-amino-2′,3′-isopropylidene adenosine [21].
T77 241-456 Sentence denotes The direct N-alkylation at room temperature did not afford the secondary amine in satisfactory yields and when increasing the temperature to enhance the reactivity of the primary amine, we noticed degradation of 17.
T78 457-653 Sentence denotes To circumvent the lack of reactivity of primary amines, a synthetic method using nitrobenzenesulfonamides (Ns-amides) as both a protecting and activating group has been developed by Fukuyama [22].
T79 654-767 Sentence denotes The main advantage of this nosyl strategy is that both alkylation and deprotection proceed under mild conditions.
T80 768-953 Sentence denotes Recently, the 2-nitrobenzenesulfonamide has been used successfully to synthetize transition state analogs of DNA methylation based on the coupling of cytosine analogs to adenosine [15].
T81 954-1078 Sentence denotes In the same way, we envisaged the coupling between 17 and the 5′-nosyl adenosine 18 to obtain the dinucleoside 1 (Scheme 2).
T82 1079-1348 Sentence denotes The building block 18 was prepared in 74% yield by reacting 4-nitrobenzenesulfonyl chloride [22] that has a similar reactivity to 2-nitrobenzenesulfonyl chloride as used in Ref. [15], with 5′-amino-2′,3′-isopropylidene adenosine prepared upon published procedures [23].
T83 1349-1507 Sentence denotes N-alkylation of Ns-amide 18 with 17 in the presence of K2CO3 in DMF at room temperature did not afford the expected dinucleoside 19, even at high temperature.
T84 1508-1660 Sentence denotes Nevertheless, according to the literature [24], the addition of a catalytic amount of KI to the reaction mixture was beneficial to give 19 in 74% yield.
T85 1661-1783 Sentence denotes Facile deprotection of 19 by treatment with a nucleophilic thiolate produced the desired secondary amine 20 in high yield.
T86 1784-1894 Sentence denotes Removal of sugar protecting groups has been accomplished in acidic medium to give dinucleoside 1 in 76% yield.
T87 1895-2060 Sentence denotes Likewise, the acidic treatment was applied to the intermediate Ns-amide 19 to afford the 4-nitrobenzenesulfonamide-containing dinucleoside 9 in 34% yield (Scheme 2).

MyTest

Id Subject Object Predicate Lexical cue
32563813-21936531-29105576 236-238 21936531 denotes 21
32563813-7086841-29105577 1344-1346 7086841 denotes 23