PMC:7291971 / 49320-50670 JSONTXT

{"project":"LitCovid-PMC-OGER-BB","denotations":[{"id":"T998","span":{"begin":46,"end":48},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T999","span":{"begin":49,"end":59},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T1000","span":{"begin":60,"end":84},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1001","span":{"begin":85,"end":87},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1002","span":{"begin":103,"end":111},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1003","span":{"begin":112,"end":113},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1004","span":{"begin":113,"end":116},"obj":"CHEBI:28714;CHEBI:28714"},{"id":"T1005","span":{"begin":117,"end":123},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T1006","span":{"begin":125,"end":130},"obj":"CHEBI:34594;CHEBI:34594"},{"id":"T1007","span":{"begin":131,"end":136},"obj":"CHEBI:46882;CHEBI:46882"},{"id":"T1008","span":{"begin":137,"end":143},"obj":"CHEBI:42241;CHEBI:42241"},{"id":"T1009","span":{"begin":145,"end":146},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1010","span":{"begin":154,"end":172},"obj":"CHEBI:28714;CHEBI:28714"},{"id":"T1011","span":{"begin":173,"end":176},"obj":"CHEBI:29354;CHEBI:29354"},{"id":"T1012","span":{"begin":207,"end":210},"obj":"CHEBI:29354;CHEBI:29354"},{"id":"T1013","span":{"begin":211,"end":217},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T1014","span":{"begin":218,"end":224},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T1015","span":{"begin":224,"end":225},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T1016","span":{"begin":225,"end":230},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1017","span":{"begin":231,"end":233},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T1018","span":{"begin":234,"end":239},"obj":"CHEBI:35589;CHEBI:35589"},{"id":"T1019","span":{"begin":242,"end":247},"obj":"CHEBI:32952;CHEBI:32952"},{"id":"T1020","span":{"begin":310,"end":323},"obj":"CHEBI:20067;CHEBI:20067"},{"id":"T1021","span":{"begin":381,"end":385},"obj":"CHEBI:32145;CHEBI:32145"},{"id":"T1022","span":{"begin":414,"end":419},"obj":"CHEBI:30808;CHEBI:30808"},{"id":"T1023","span":{"begin":1014,"end":1017},"obj":"CHEBI:36927;CHEBI:36927"},{"id":"T32363","span":{"begin":46,"end":48},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T13211","span":{"begin":49,"end":59},"obj":"CHEBI:30756;CHEBI:30756"},{"id":"T96959","span":{"begin":60,"end":84},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T81968","span":{"begin":85,"end":87},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T62563","span":{"begin":103,"end":111},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T71718","span":{"begin":112,"end":113},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T20039","span":{"begin":113,"end":116},"obj":"CHEBI:28714;CHEBI:28714"},{"id":"T58470","span":{"begin":117,"end":123},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T88741","span":{"begin":125,"end":130},"obj":"CHEBI:34594;CHEBI:34594"},{"id":"T90855","span":{"begin":131,"end":136},"obj":"CHEBI:46882;CHEBI:46882"},{"id":"T4988","span":{"begin":137,"end":143},"obj":"CHEBI:42241;CHEBI:42241"},{"id":"T98861","span":{"begin":145,"end":146},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T30207","span":{"begin":154,"end":172},"obj":"CHEBI:28714;CHEBI:28714"},{"id":"T63301","span":{"begin":173,"end":176},"obj":"CHEBI:29354;CHEBI:29354"},{"id":"T91694","span":{"begin":207,"end":210},"obj":"CHEBI:29354;CHEBI:29354"},{"id":"T32425","span":{"begin":211,"end":217},"obj":"CHEBI:29309;CHEBI:29309"},{"id":"T53106","span":{"begin":218,"end":224},"obj":"CHEBI:26911;CHEBI:26911"},{"id":"T98099","span":{"begin":224,"end":225},"obj":"CHEBI:15533;CHEBI:15533"},{"id":"T44173","span":{"begin":225,"end":230},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T15637","span":{"begin":231,"end":233},"obj":"CHEBI:53233;CHEBI:53233"},{"id":"T88656","span":{"begin":234,"end":239},"obj":"CHEBI:35589;CHEBI:35589"},{"id":"T83607","span":{"begin":242,"end":247},"obj":"CHEBI:32952;CHEBI:32952"},{"id":"T96207","span":{"begin":310,"end":323},"obj":"CHEBI:20067;CHEBI:20067"},{"id":"T31939","span":{"begin":381,"end":385},"obj":"CHEBI:32145;CHEBI:32145"},{"id":"T15973","span":{"begin":414,"end":419},"obj":"CHEBI:30808;CHEBI:30808"},{"id":"T79430","span":{"begin":1014,"end":1017},"obj":"CHEBI:36927;CHEBI:36927"}],"text":"4.1.14 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}(butyl)amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (23)\nFollowing method D with 20 (80 mg, 97 μmol, 1.00 eq) and 1-bromobutane, 23 (40 mg, 47%) was obtained as a white solid. Rf 0.48 (MeOH/DCM 5:95). 1H NMR (600 MHz, CDCl3) δ 8.33 (s, 2H), 8.16 (s, 1H), 7.92 (s, 1H), 6.11 (d, J = 3.8 Hz, 1H), 6.03 (d, J = 2.3 Hz, 1H), 5.77 (br. s, 4H), 5.47 (dd, J = 6.4 Hz, J = 2.2 Hz, 1H), 4.91 (dd, J = 6.4 Hz, J = 3.2 Hz, 1H), 4.51 (t, J = 5.1 Hz, 1H), 4.37–4.24 (m, 2H), 4.09 (dt, J = 5.9 Hz, J = 3.0 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.7 Hz, 1H), 3.76 (dd, J = 11.5 Hz, J = 2.8 Hz, 1H), 3.70–3.61 (m, 2H), 2.77–2.68 (m, 3H), 2.63 (dd, J = 13.5 Hz, J = 7.0 Hz, 1H), 2.46–2.37 (m, 2H), 1.59 (s, 3H), 1.38 (s, 3H), 1.31–1.22 (m, 2H), 1.22–1.12 (m, 2H), 0.92 (s, 9H), 0.91 (s, 9H), 0.82 (t, J = 7.3 Hz, 3H), 0.10–0.08 (m, 12H). 13C NMR (150 MHz, CDCl3) δ 155.6, 155.5, 153.2, 153.1, 149.8, 149.4, 140.2, 139.7, 120.5, 120.3, 114.4, 91.2, 87.2, 85.8, 84.9, 84.0, 83.4, 82.4, 69.9, 69.3, 62.0, 56.7, 55.1, 53.9, 29.2, 27.2, 26.1, 25.9, 25.5, 20.5, 18.6, 18.2, 14.1, −4.4, −4.6, −5.2, −5.2. HRMS (ESI+): m/z calcd for C46H72N11O7Si2 [M+H]+: 884.4998, found: 884.5002."}

{"project":"LitCovid-PubTator","denotations":[{"id":"864","span":{"begin":310,"end":323},"obj":"Chemical"},{"id":"865","span":{"begin":381,"end":385},"obj":"Chemical"},{"id":"866","span":{"begin":386,"end":389},"obj":"Chemical"},{"id":"867","span":{"begin":397,"end":399},"obj":"Chemical"},{"id":"868","span":{"begin":414,"end":419},"obj":"Chemical"},{"id":"869","span":{"begin":432,"end":434},"obj":"Chemical"},{"id":"870","span":{"begin":446,"end":448},"obj":"Chemical"},{"id":"871","span":{"begin":460,"end":462},"obj":"Chemical"},{"id":"872","span":{"begin":486,"end":488},"obj":"Chemical"},{"id":"873","span":{"begin":512,"end":514},"obj":"Chemical"},{"id":"874","span":{"begin":1301,"end":1315},"obj":"Chemical"},{"id":"875","span":{"begin":1274,"end":1278},"obj":"Disease"}],"attributes":[{"id":"A864","pred":"tao:has_database_id","subj":"864","obj":"MESH:C047757"},{"id":"A869","pred":"tao:has_database_id","subj":"869","obj":"MESH:D003903"}],"namespaces":[{"prefix":"Tax","uri":"https://www.ncbi.nlm.nih.gov/taxonomy/"},{"prefix":"MESH","uri":"https://id.nlm.nih.gov/mesh/"},{"prefix":"Gene","uri":"https://www.ncbi.nlm.nih.gov/gene/"},{"prefix":"CVCL","uri":"https://web.expasy.org/cellosaurus/CVCL_"}],"text":"4.1.14 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}(butyl)amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (23)\nFollowing method D with 20 (80 mg, 97 μmol, 1.00 eq) and 1-bromobutane, 23 (40 mg, 47%) was obtained as a white solid. Rf 0.48 (MeOH/DCM 5:95). 1H NMR (600 MHz, CDCl3) δ 8.33 (s, 2H), 8.16 (s, 1H), 7.92 (s, 1H), 6.11 (d, J = 3.8 Hz, 1H), 6.03 (d, J = 2.3 Hz, 1H), 5.77 (br. s, 4H), 5.47 (dd, J = 6.4 Hz, J = 2.2 Hz, 1H), 4.91 (dd, J = 6.4 Hz, J = 3.2 Hz, 1H), 4.51 (t, J = 5.1 Hz, 1H), 4.37–4.24 (m, 2H), 4.09 (dt, J = 5.9 Hz, J = 3.0 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.7 Hz, 1H), 3.76 (dd, J = 11.5 Hz, J = 2.8 Hz, 1H), 3.70–3.61 (m, 2H), 2.77–2.68 (m, 3H), 2.63 (dd, J = 13.5 Hz, J = 7.0 Hz, 1H), 2.46–2.37 (m, 2H), 1.59 (s, 3H), 1.38 (s, 3H), 1.31–1.22 (m, 2H), 1.22–1.12 (m, 2H), 0.92 (s, 9H), 0.91 (s, 9H), 0.82 (t, J = 7.3 Hz, 3H), 0.10–0.08 (m, 12H). 13C NMR (150 MHz, CDCl3) δ 155.6, 155.5, 153.2, 153.1, 149.8, 149.4, 140.2, 139.7, 120.5, 120.3, 114.4, 91.2, 87.2, 85.8, 84.9, 84.0, 83.4, 82.4, 69.9, 69.3, 62.0, 56.7, 55.1, 53.9, 29.2, 27.2, 26.1, 25.9, 25.5, 20.5, 18.6, 18.2, 14.1, −4.4, −4.6, −5.2, −5.2. HRMS (ESI+): m/z calcd for C46H72N11O7Si2 [M+H]+: 884.4998, found: 884.5002."}

{"project":"LitCovid-PD-CLO","denotations":[{"id":"T329","span":{"begin":357,"end":358},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T330","span":{"begin":1317,"end":1320},"obj":"http://purl.obolibrary.org/obo/CLO_0007706"}],"text":"4.1.14 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}(butyl)amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (23)\nFollowing method D with 20 (80 mg, 97 μmol, 1.00 eq) and 1-bromobutane, 23 (40 mg, 47%) was obtained as a white solid. Rf 0.48 (MeOH/DCM 5:95). 1H NMR (600 MHz, CDCl3) δ 8.33 (s, 2H), 8.16 (s, 1H), 7.92 (s, 1H), 6.11 (d, J = 3.8 Hz, 1H), 6.03 (d, J = 2.3 Hz, 1H), 5.77 (br. s, 4H), 5.47 (dd, J = 6.4 Hz, J = 2.2 Hz, 1H), 4.91 (dd, J = 6.4 Hz, J = 3.2 Hz, 1H), 4.51 (t, J = 5.1 Hz, 1H), 4.37–4.24 (m, 2H), 4.09 (dt, J = 5.9 Hz, J = 3.0 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.7 Hz, 1H), 3.76 (dd, J = 11.5 Hz, J = 2.8 Hz, 1H), 3.70–3.61 (m, 2H), 2.77–2.68 (m, 3H), 2.63 (dd, J = 13.5 Hz, J = 7.0 Hz, 1H), 2.46–2.37 (m, 2H), 1.59 (s, 3H), 1.38 (s, 3H), 1.31–1.22 (m, 2H), 1.22–1.12 (m, 2H), 0.92 (s, 9H), 0.91 (s, 9H), 0.82 (t, J = 7.3 Hz, 3H), 0.10–0.08 (m, 12H). 13C NMR (150 MHz, CDCl3) δ 155.6, 155.5, 153.2, 153.1, 149.8, 149.4, 140.2, 139.7, 120.5, 120.3, 114.4, 91.2, 87.2, 85.8, 84.9, 84.0, 83.4, 82.4, 69.9, 69.3, 62.0, 56.7, 55.1, 53.9, 29.2, 27.2, 26.1, 25.9, 25.5, 20.5, 18.6, 18.2, 14.1, −4.4, −4.6, −5.2, −5.2. HRMS (ESI+): m/z calcd for C46H72N11O7Si2 [M+H]+: 884.4998, found: 884.5002."}

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bj":"http://purl.obolibrary.org/obo/CHEBI_85365"}],"text":"4.1.14 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}(butyl)amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (23)\nFollowing method D with 20 (80 mg, 97 μmol, 1.00 eq) and 1-bromobutane, 23 (40 mg, 47%) was obtained as a white solid. Rf 0.48 (MeOH/DCM 5:95). 1H NMR (600 MHz, CDCl3) δ 8.33 (s, 2H), 8.16 (s, 1H), 7.92 (s, 1H), 6.11 (d, J = 3.8 Hz, 1H), 6.03 (d, J = 2.3 Hz, 1H), 5.77 (br. s, 4H), 5.47 (dd, J = 6.4 Hz, J = 2.2 Hz, 1H), 4.91 (dd, J = 6.4 Hz, J = 3.2 Hz, 1H), 4.51 (t, J = 5.1 Hz, 1H), 4.37–4.24 (m, 2H), 4.09 (dt, J = 5.9 Hz, J = 3.0 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.7 Hz, 1H), 3.76 (dd, J = 11.5 Hz, J = 2.8 Hz, 1H), 3.70–3.61 (m, 2H), 2.77–2.68 (m, 3H), 2.63 (dd, J = 13.5 Hz, J = 7.0 Hz, 1H), 2.46–2.37 (m, 2H), 1.59 (s, 3H), 1.38 (s, 3H), 1.31–1.22 (m, 2H), 1.22–1.12 (m, 2H), 0.92 (s, 9H), 0.91 (s, 9H), 0.82 (t, J = 7.3 Hz, 3H), 0.10–0.08 (m, 12H). 13C NMR (150 MHz, CDCl3) δ 155.6, 155.5, 153.2, 153.1, 149.8, 149.4, 140.2, 139.7, 120.5, 120.3, 114.4, 91.2, 87.2, 85.8, 84.9, 84.0, 83.4, 82.4, 69.9, 69.3, 62.0, 56.7, 55.1, 53.9, 29.2, 27.2, 26.1, 25.9, 25.5, 20.5, 18.6, 18.2, 14.1, −4.4, −4.6, −5.2, −5.2. HRMS (ESI+): m/z calcd for C46H72N11O7Si2 [M+H]+: 884.4998, found: 884.5002."}

{"project":"LitCovid-PD-HP","denotations":[{"id":"T19","span":{"begin":386,"end":389},"obj":"Phenotype"}],"attributes":[{"id":"A19","pred":"hp_id","subj":"T19","obj":"http://purl.obolibrary.org/obo/HP_0001644"}],"text":"4.1.14 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}(butyl)amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (23)\nFollowing method D with 20 (80 mg, 97 μmol, 1.00 eq) and 1-bromobutane, 23 (40 mg, 47%) was obtained as a white solid. Rf 0.48 (MeOH/DCM 5:95). 1H NMR (600 MHz, CDCl3) δ 8.33 (s, 2H), 8.16 (s, 1H), 7.92 (s, 1H), 6.11 (d, J = 3.8 Hz, 1H), 6.03 (d, J = 2.3 Hz, 1H), 5.77 (br. s, 4H), 5.47 (dd, J = 6.4 Hz, J = 2.2 Hz, 1H), 4.91 (dd, J = 6.4 Hz, J = 3.2 Hz, 1H), 4.51 (t, J = 5.1 Hz, 1H), 4.37–4.24 (m, 2H), 4.09 (dt, J = 5.9 Hz, J = 3.0 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.7 Hz, 1H), 3.76 (dd, J = 11.5 Hz, J = 2.8 Hz, 1H), 3.70–3.61 (m, 2H), 2.77–2.68 (m, 3H), 2.63 (dd, J = 13.5 Hz, J = 7.0 Hz, 1H), 2.46–2.37 (m, 2H), 1.59 (s, 3H), 1.38 (s, 3H), 1.31–1.22 (m, 2H), 1.22–1.12 (m, 2H), 0.92 (s, 9H), 0.91 (s, 9H), 0.82 (t, J = 7.3 Hz, 3H), 0.10–0.08 (m, 12H). 13C NMR (150 MHz, CDCl3) δ 155.6, 155.5, 153.2, 153.1, 149.8, 149.4, 140.2, 139.7, 120.5, 120.3, 114.4, 91.2, 87.2, 85.8, 84.9, 84.0, 83.4, 82.4, 69.9, 69.3, 62.0, 56.7, 55.1, 53.9, 29.2, 27.2, 26.1, 25.9, 25.5, 20.5, 18.6, 18.2, 14.1, −4.4, −4.6, −5.2, −5.2. HRMS (ESI+): m/z calcd for C46H72N11O7Si2 [M+H]+: 884.4998, found: 884.5002."}

{"project":"LitCovid-sentences","denotations":[{"id":"T358","span":{"begin":0,"end":252},"obj":"Sentence"},{"id":"T359","span":{"begin":253,"end":371},"obj":"Sentence"},{"id":"T360","span":{"begin":372,"end":396},"obj":"Sentence"},{"id":"T361","span":{"begin":397,"end":1013},"obj":"Sentence"},{"id":"T362","span":{"begin":1014,"end":1273},"obj":"Sentence"},{"id":"T363","span":{"begin":1274,"end":1323},"obj":"Sentence"},{"id":"T364","span":{"begin":1324,"end":1340},"obj":"Sentence"},{"id":"T365","span":{"begin":1341,"end":1350},"obj":"Sentence"}],"namespaces":[{"prefix":"_base","uri":"http://pubannotation.org/ontology/tao.owl#"}],"text":"4.1.14 9-[(2R,5R)-3-[2-({[(4R,6R)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d] [1,3]dioxol-4-yl]methyl}(butyl)amino)ethoxy]-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-9H-purin-6-amine (23)\nFollowing method D with 20 (80 mg, 97 μmol, 1.00 eq) and 1-bromobutane, 23 (40 mg, 47%) was obtained as a white solid. Rf 0.48 (MeOH/DCM 5:95). 1H NMR (600 MHz, CDCl3) δ 8.33 (s, 2H), 8.16 (s, 1H), 7.92 (s, 1H), 6.11 (d, J = 3.8 Hz, 1H), 6.03 (d, J = 2.3 Hz, 1H), 5.77 (br. s, 4H), 5.47 (dd, J = 6.4 Hz, J = 2.2 Hz, 1H), 4.91 (dd, J = 6.4 Hz, J = 3.2 Hz, 1H), 4.51 (t, J = 5.1 Hz, 1H), 4.37–4.24 (m, 2H), 4.09 (dt, J = 5.9 Hz, J = 3.0 Hz, 1H), 3.99 (dd, J = 11.5 Hz, J = 3.7 Hz, 1H), 3.76 (dd, J = 11.5 Hz, J = 2.8 Hz, 1H), 3.70–3.61 (m, 2H), 2.77–2.68 (m, 3H), 2.63 (dd, J = 13.5 Hz, J = 7.0 Hz, 1H), 2.46–2.37 (m, 2H), 1.59 (s, 3H), 1.38 (s, 3H), 1.31–1.22 (m, 2H), 1.22–1.12 (m, 2H), 0.92 (s, 9H), 0.91 (s, 9H), 0.82 (t, J = 7.3 Hz, 3H), 0.10–0.08 (m, 12H). 13C NMR (150 MHz, CDCl3) δ 155.6, 155.5, 153.2, 153.1, 149.8, 149.4, 140.2, 139.7, 120.5, 120.3, 114.4, 91.2, 87.2, 85.8, 84.9, 84.0, 83.4, 82.4, 69.9, 69.3, 62.0, 56.7, 55.1, 53.9, 29.2, 27.2, 26.1, 25.9, 25.5, 20.5, 18.6, 18.2, 14.1, −4.4, −4.6, −5.2, −5.2. HRMS (ESI+): m/z calcd for C46H72N11O7Si2 [M+H]+: 884.4998, found: 884.5002."}