PMC:7291971 / 10978-11755 JSONTXT

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    LitCovid-PMC-OGER-BB

    {"project":"LitCovid-PMC-OGER-BB","denotations":[{"id":"T219","span":{"begin":13,"end":26},"obj":"CHEBI:23447;CHEBI:23447"},{"id":"T220","span":{"begin":36,"end":41},"obj":"CHEBI:32031;CHEBI:32031"},{"id":"T221","span":{"begin":80,"end":85},"obj":"CHEBI:32031;CHEBI:32031"},{"id":"T222","span":{"begin":117,"end":120},"obj":"CHEBI:15377;CHEBI:15377"},{"id":"T223","span":{"begin":175,"end":179},"obj":"CHEBI:16236;CHEBI:16236"},{"id":"T224","span":{"begin":247,"end":250},"obj":"CHEBI:15377;CHEBI:15377"},{"id":"T225","span":{"begin":277,"end":284},"obj":"CHEBI:15377;CHEBI:15377"},{"id":"T226","span":{"begin":285,"end":293},"obj":"CHEBI:75958;CHEBI:75958"},{"id":"T227","span":{"begin":294,"end":298},"obj":"CHEBI:48607;CHEBI:48607"},{"id":"T228","span":{"begin":327,"end":330},"obj":"CHEBI:15377;CHEBI:15377"},{"id":"T229","span":{"begin":365,"end":368},"obj":"CHEBI:15377;CHEBI:15377"},{"id":"T230","span":{"begin":395,"end":398},"obj":"CHEBI:62946;CHEBI:62946"},{"id":"T231","span":{"begin":399,"end":403},"obj":"CHEBI:32145;CHEBI:32145"},{"id":"T232","span":{"begin":427,"end":440},"obj":"CHEBI:62946;CHEBI:62946"},{"id":"T233","span":{"begin":488,"end":490},"obj":"CHEBI:17824;CHEBI:17824"},{"id":"T234","span":{"begin":490,"end":495},"obj":"CHEBI:47265;CHEBI:47265"},{"id":"T235","span":{"begin":495,"end":511},"obj":"CHEBI:17824;CHEBI:17824"},{"id":"T236","span":{"begin":643,"end":646},"obj":"CHEBI:15377;CHEBI:15377"},{"id":"T237","span":{"begin":731,"end":738},"obj":"CHEBI:15377;CHEBI:15377"},{"id":"T238","span":{"begin":739,"end":747},"obj":"CHEBI:75958;CHEBI:75958"},{"id":"T239","span":{"begin":748,"end":752},"obj":"CHEBI:32145;CHEBI:32145"}],"text":"Synthesis of dinucleosides 1–9. (a) K2CO3, KI, DMF, 50 °C, 24 h, 74%; (b) PhSH, K2CO3, DMF, 25 °C, 2 h, 76%; (c) TFA/H2O 8/2, 25 °C, 3 h, 76% for 1 and 34% for 9; (d) (i) 21, AcOH, CH2Cl2, 25 °C, 2 h, (ii) NaBH(OAc)3, 25 °C, 2 h, 93%; (e) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 2 M aqueous solution LiOH, 25 °C, 0.5 h, 32%; (f) TFA/H2O 8/2, 25 °C, 3 h, 35%; (g) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 7 M NH3/MeOH, 30 °C, 24 h, 38%; (h) 1-bromobutane, DIEA, NMP, microwave 110 °C, 4 h, 47% for 23; 1-bromo-3-phenylpropane, DIEA, NMP, microwave 110 °C, 4 h, 53% for 24, methyl 4-bromobutyrate, DIEA, NMP, microwave 110 °C, 3.5 h, 58% for 25; (i) (i) TFA/H2O 8/2, 25 °C, 6 h, 72% for 5; 3 h, 28% for 6; 5.5 h, 60% for 7; 5.5 h for 8. (ii) 2 M aqueous solution LiOH, 0 °C, 0.5 h, 36% for 8."}

    LitCovid-PD-FMA-UBERON

    {"project":"LitCovid-PD-FMA-UBERON","denotations":[{"id":"T49","span":{"begin":198,"end":205},"obj":"Body_part"},{"id":"T50","span":{"begin":265,"end":272},"obj":"Body_part"},{"id":"T51","span":{"begin":383,"end":390},"obj":"Body_part"}],"attributes":[{"id":"A49","pred":"fma_id","subj":"T49","obj":"http://purl.org/sig/ont/fma/fma278665"},{"id":"A50","pred":"fma_id","subj":"T50","obj":"http://purl.org/sig/ont/fma/fma278665"},{"id":"A51","pred":"fma_id","subj":"T51","obj":"http://purl.org/sig/ont/fma/fma278665"}],"text":"Synthesis of dinucleosides 1–9. (a) K2CO3, KI, DMF, 50 °C, 24 h, 74%; (b) PhSH, K2CO3, DMF, 25 °C, 2 h, 76%; (c) TFA/H2O 8/2, 25 °C, 3 h, 76% for 1 and 34% for 9; (d) (i) 21, AcOH, CH2Cl2, 25 °C, 2 h, (ii) NaBH(OAc)3, 25 °C, 2 h, 93%; (e) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 2 M aqueous solution LiOH, 25 °C, 0.5 h, 32%; (f) TFA/H2O 8/2, 25 °C, 3 h, 35%; (g) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 7 M NH3/MeOH, 30 °C, 24 h, 38%; (h) 1-bromobutane, DIEA, NMP, microwave 110 °C, 4 h, 47% for 23; 1-bromo-3-phenylpropane, DIEA, NMP, microwave 110 °C, 4 h, 53% for 24, methyl 4-bromobutyrate, DIEA, NMP, microwave 110 °C, 3.5 h, 58% for 25; (i) (i) TFA/H2O 8/2, 25 °C, 6 h, 72% for 5; 3 h, 28% for 6; 5.5 h, 60% for 7; 5.5 h for 8. (ii) 2 M aqueous solution LiOH, 0 °C, 0.5 h, 36% for 8."}

    LitCovid-PubTator

    {"project":"LitCovid-PubTator","denotations":[{"id":"109","span":{"begin":13,"end":26},"obj":"Chemical"},{"id":"110","span":{"begin":117,"end":120},"obj":"Chemical"},{"id":"111","span":{"begin":247,"end":250},"obj":"Chemical"},{"id":"112","span":{"begin":327,"end":330},"obj":"Chemical"},{"id":"113","span":{"begin":365,"end":368},"obj":"Chemical"},{"id":"114","span":{"begin":643,"end":646},"obj":"Chemical"},{"id":"115","span":{"begin":748,"end":752},"obj":"Chemical"}],"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":"Synthesis of dinucleosides 1–9. (a) K2CO3, KI, DMF, 50 °C, 24 h, 74%; (b) PhSH, K2CO3, DMF, 25 °C, 2 h, 76%; (c) TFA/H2O 8/2, 25 °C, 3 h, 76% for 1 and 34% for 9; (d) (i) 21, AcOH, CH2Cl2, 25 °C, 2 h, (ii) NaBH(OAc)3, 25 °C, 2 h, 93%; (e) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 2 M aqueous solution LiOH, 25 °C, 0.5 h, 32%; (f) TFA/H2O 8/2, 25 °C, 3 h, 35%; (g) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 7 M NH3/MeOH, 30 °C, 24 h, 38%; (h) 1-bromobutane, DIEA, NMP, microwave 110 °C, 4 h, 47% for 23; 1-bromo-3-phenylpropane, DIEA, NMP, microwave 110 °C, 4 h, 53% for 24, methyl 4-bromobutyrate, DIEA, NMP, microwave 110 °C, 3.5 h, 58% for 25; (i) (i) TFA/H2O 8/2, 25 °C, 6 h, 72% for 5; 3 h, 28% for 6; 5.5 h, 60% for 7; 5.5 h for 8. (ii) 2 M aqueous solution LiOH, 0 °C, 0.5 h, 36% for 8."}

    LitCovid-PD-CLO

    {"project":"LitCovid-PD-CLO","denotations":[{"id":"T77","span":{"begin":33,"end":34},"obj":"http://purl.obolibrary.org/obo/CLO_0001020"},{"id":"T78","span":{"begin":71,"end":72},"obj":"http://purl.obolibrary.org/obo/CLO_0001021"},{"id":"T79","span":{"begin":96,"end":100},"obj":"http://purl.obolibrary.org/obo/CLO_0002105"},{"id":"T80","span":{"begin":96,"end":100},"obj":"http://purl.obolibrary.org/obo/CLO_0051742"},{"id":"T81","span":{"begin":123,"end":128},"obj":"http://purl.obolibrary.org/obo/CLO_0001196"},{"id":"T82","span":{"begin":152,"end":154},"obj":"http://purl.obolibrary.org/obo/CLO_0001302"},{"id":"T83","span":{"begin":167,"end":173},"obj":"http://purl.obolibrary.org/obo/CLO_0004316"},{"id":"T84","span":{"begin":193,"end":197},"obj":"http://purl.obolibrary.org/obo/CLO_0002105"},{"id":"T85","span":{"begin":193,"end":197},"obj":"http://purl.obolibrary.org/obo/CLO_0051742"},{"id":"T86","span":{"begin":222,"end":226},"obj":"http://purl.obolibrary.org/obo/CLO_0002105"},{"id":"T87","span":{"begin":222,"end":226},"obj":"http://purl.obolibrary.org/obo/CLO_0051742"},{"id":"T88","span":{"begin":253,"end":258},"obj":"http://purl.obolibrary.org/obo/CLO_0001196"},{"id":"T89","span":{"begin":333,"end":338},"obj":"http://purl.obolibrary.org/obo/CLO_0001196"},{"id":"T90","span":{"begin":348,"end":350},"obj":"http://purl.obolibrary.org/obo/CLO_0001000"},{"id":"T91","span":{"begin":371,"end":376},"obj":"http://purl.obolibrary.org/obo/CLO_0001196"},{"id":"T92","span":{"begin":468,"end":472},"obj":"http://purl.obolibrary.org/obo/CLO_0037284"},{"id":"T93","span":{"begin":539,"end":543},"obj":"http://purl.obolibrary.org/obo/CLO_0037284"},{"id":"T94","span":{"begin":649,"end":654},"obj":"http://purl.obolibrary.org/obo/CLO_0001196"},{"id":"T95","span":{"begin":656,"end":660},"obj":"http://purl.obolibrary.org/obo/CLO_0002140"},{"id":"T96","span":{"begin":656,"end":660},"obj":"http://purl.obolibrary.org/obo/CLO_0051387"},{"id":"T97","span":{"begin":656,"end":660},"obj":"http://purl.obolibrary.org/obo/CLO_0051684"},{"id":"T98","span":{"begin":656,"end":660},"obj":"http://purl.obolibrary.org/obo/CLO_0051685"},{"id":"T99","span":{"begin":656,"end":660},"obj":"http://purl.obolibrary.org/obo/CLO_0051686"},{"id":"T100","span":{"begin":677,"end":682},"obj":"http://purl.obolibrary.org/obo/CLO_0003588"},{"id":"T101","span":{"begin":767,"end":769},"obj":"http://purl.obolibrary.org/obo/CLO_0001313"}],"text":"Synthesis of dinucleosides 1–9. (a) K2CO3, KI, DMF, 50 °C, 24 h, 74%; (b) PhSH, K2CO3, DMF, 25 °C, 2 h, 76%; (c) TFA/H2O 8/2, 25 °C, 3 h, 76% for 1 and 34% for 9; (d) (i) 21, AcOH, CH2Cl2, 25 °C, 2 h, (ii) NaBH(OAc)3, 25 °C, 2 h, 93%; (e) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 2 M aqueous solution LiOH, 25 °C, 0.5 h, 32%; (f) TFA/H2O 8/2, 25 °C, 3 h, 35%; (g) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 7 M NH3/MeOH, 30 °C, 24 h, 38%; (h) 1-bromobutane, DIEA, NMP, microwave 110 °C, 4 h, 47% for 23; 1-bromo-3-phenylpropane, DIEA, NMP, microwave 110 °C, 4 h, 53% for 24, methyl 4-bromobutyrate, DIEA, NMP, microwave 110 °C, 3.5 h, 58% for 25; (i) (i) TFA/H2O 8/2, 25 °C, 6 h, 72% for 5; 3 h, 28% for 6; 5.5 h, 60% for 7; 5.5 h for 8. (ii) 2 M aqueous solution LiOH, 0 °C, 0.5 h, 36% for 8."}

    LitCovid-PD-CHEBI

    {"project":"LitCovid-PD-CHEBI","denotations":[{"id":"T149","span":{"begin":36,"end":41},"obj":"Chemical"},{"id":"T150","span":{"begin":43,"end":45},"obj":"Chemical"},{"id":"T152","span":{"begin":47,"end":50},"obj":"Chemical"},{"id":"T153","span":{"begin":80,"end":85},"obj":"Chemical"},{"id":"T154","span":{"begin":87,"end":90},"obj":"Chemical"},{"id":"T155","span":{"begin":113,"end":116},"obj":"Chemical"},{"id":"T156","span":{"begin":117,"end":120},"obj":"Chemical"},{"id":"T157","span":{"begin":175,"end":179},"obj":"Chemical"},{"id":"T158","span":{"begin":243,"end":246},"obj":"Chemical"},{"id":"T159","span":{"begin":247,"end":250},"obj":"Chemical"},{"id":"T160","span":{"begin":285,"end":293},"obj":"Chemical"},{"id":"T161","span":{"begin":294,"end":298},"obj":"Chemical"},{"id":"T162","span":{"begin":323,"end":326},"obj":"Chemical"},{"id":"T163","span":{"begin":327,"end":330},"obj":"Chemical"},{"id":"T164","span":{"begin":361,"end":364},"obj":"Chemical"},{"id":"T165","span":{"begin":365,"end":368},"obj":"Chemical"},{"id":"T166","span":{"begin":395,"end":398},"obj":"Chemical"},{"id":"T167","span":{"begin":399,"end":403},"obj":"Chemical"},{"id":"T168","span":{"begin":448,"end":451},"obj":"Chemical"},{"id":"T171","span":{"begin":490,"end":495},"obj":"Chemical"},{"id":"T173","span":{"begin":519,"end":522},"obj":"Chemical"},{"id":"T176","span":{"begin":559,"end":565},"obj":"Chemical"},{"id":"T178","span":{"begin":589,"end":592},"obj":"Chemical"},{"id":"T181","span":{"begin":639,"end":642},"obj":"Chemical"},{"id":"T182","span":{"begin":643,"end":646},"obj":"Chemical"},{"id":"T183","span":{"begin":739,"end":747},"obj":"Chemical"},{"id":"T184","span":{"begin":748,"end":752},"obj":"Chemical"}],"attributes":[{"id":"A149","pred":"chebi_id","subj":"T149","obj":"http://purl.obolibrary.org/obo/CHEBI_131526"},{"id":"A150","pred":"chebi_id","subj":"T150","obj":"http://purl.obolibrary.org/obo/CHEBI_74559"},{"id":"A151","pred":"chebi_id","subj":"T150","obj":"http://purl.obolibrary.org/obo/CHEBI_8346"},{"id":"A152","pred":"chebi_id","subj":"T152","obj":"http://purl.obolibrary.org/obo/CHEBI_17741"},{"id":"A153","pred":"chebi_id","subj":"T153","obj":"http://purl.obolibrary.org/obo/CHEBI_131526"},{"id":"A154","pred":"chebi_id","subj":"T154","obj":"http://purl.obolibrary.org/obo/CHEBI_17741"},{"id":"A155","pred":"chebi_id","subj":"T155","obj":"http://purl.obolibrary.org/obo/CHEBI_45892"},{"id":"A156","pred":"chebi_id","subj":"T156","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A157","pred":"chebi_id","subj":"T157","obj":"http://purl.obolibrary.org/obo/CHEBI_15366"},{"id":"A158","pred":"chebi_id","subj":"T158","obj":"http://purl.obolibrary.org/obo/CHEBI_45892"},{"id":"A159","pred":"chebi_id","subj":"T159","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A160","pred":"chebi_id","subj":"T160","obj":"http://purl.obolibrary.org/obo/CHEBI_75958"},{"id":"A161","pred":"chebi_id","subj":"T161","obj":"http://purl.obolibrary.org/obo/CHEBI_33979"},{"id":"A162","pred":"chebi_id","subj":"T162","obj":"http://purl.obolibrary.org/obo/CHEBI_45892"},{"id":"A163","pred":"chebi_id","subj":"T163","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A164","pred":"chebi_id","subj":"T164","obj":"http://purl.obolibrary.org/obo/CHEBI_45892"},{"id":"A165","pred":"chebi_id","subj":"T165","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A166","pred":"chebi_id","subj":"T166","obj":"http://purl.obolibrary.org/obo/CHEBI_16134"},{"id":"A167","pred":"chebi_id","subj":"T167","obj":"http://purl.obolibrary.org/obo/CHEBI_17790"},{"id":"A168","pred":"chebi_id","subj":"T168","obj":"http://purl.obolibrary.org/obo/CHEBI_17188"},{"id":"A169","pred":"chebi_id","subj":"T168","obj":"http://purl.obolibrary.org/obo/CHEBI_25608"},{"id":"A170","pred":"chebi_id","subj":"T168","obj":"http://purl.obolibrary.org/obo/CHEBI_7307"},{"id":"A171","pred":"chebi_id","subj":"T171","obj":"http://purl.obolibrary.org/obo/CHEBI_22927"},{"id":"A172","pred":"chebi_id","subj":"T171","obj":"http://purl.obolibrary.org/obo/CHEBI_47265"},{"id":"A173","pred":"chebi_id","subj":"T173","obj":"http://purl.obolibrary.org/obo/CHEBI_17188"},{"id":"A174","pred":"chebi_id","subj":"T173","obj":"http://purl.obolibrary.org/obo/CHEBI_25608"},{"id":"A175","pred":"chebi_id","subj":"T173","obj":"http://purl.obolibrary.org/obo/CHEBI_7307"},{"id":"A176","pred":"chebi_id","subj":"T176","obj":"http://purl.obolibrary.org/obo/CHEBI_32875"},{"id":"A177","pred":"chebi_id","subj":"T176","obj":"http://purl.obolibrary.org/obo/CHEBI_29309"},{"id":"A178","pred":"chebi_id","subj":"T178","obj":"http://purl.obolibrary.org/obo/CHEBI_17188"},{"id":"A179","pred":"chebi_id","subj":"T178","obj":"http://purl.obolibrary.org/obo/CHEBI_25608"},{"id":"A180","pred":"chebi_id","subj":"T178","obj":"http://purl.obolibrary.org/obo/CHEBI_7307"},{"id":"A181","pred":"chebi_id","subj":"T181","obj":"http://purl.obolibrary.org/obo/CHEBI_45892"},{"id":"A182","pred":"chebi_id","subj":"T182","obj":"http://purl.obolibrary.org/obo/CHEBI_15377"},{"id":"A183","pred":"chebi_id","subj":"T183","obj":"http://purl.obolibrary.org/obo/CHEBI_75958"},{"id":"A184","pred":"chebi_id","subj":"T184","obj":"http://purl.obolibrary.org/obo/CHEBI_33979"}],"text":"Synthesis of dinucleosides 1–9. (a) K2CO3, KI, DMF, 50 °C, 24 h, 74%; (b) PhSH, K2CO3, DMF, 25 °C, 2 h, 76%; (c) TFA/H2O 8/2, 25 °C, 3 h, 76% for 1 and 34% for 9; (d) (i) 21, AcOH, CH2Cl2, 25 °C, 2 h, (ii) NaBH(OAc)3, 25 °C, 2 h, 93%; (e) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 2 M aqueous solution LiOH, 25 °C, 0.5 h, 32%; (f) TFA/H2O 8/2, 25 °C, 3 h, 35%; (g) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 7 M NH3/MeOH, 30 °C, 24 h, 38%; (h) 1-bromobutane, DIEA, NMP, microwave 110 °C, 4 h, 47% for 23; 1-bromo-3-phenylpropane, DIEA, NMP, microwave 110 °C, 4 h, 53% for 24, methyl 4-bromobutyrate, DIEA, NMP, microwave 110 °C, 3.5 h, 58% for 25; (i) (i) TFA/H2O 8/2, 25 °C, 6 h, 72% for 5; 3 h, 28% for 6; 5.5 h, 60% for 7; 5.5 h for 8. (ii) 2 M aqueous solution LiOH, 0 °C, 0.5 h, 36% for 8."}

    LitCovid-PD-GO-BP

    {"project":"LitCovid-PD-GO-BP","denotations":[{"id":"T26","span":{"begin":0,"end":9},"obj":"http://purl.obolibrary.org/obo/GO_0009058"}],"text":"Synthesis of dinucleosides 1–9. (a) K2CO3, KI, DMF, 50 °C, 24 h, 74%; (b) PhSH, K2CO3, DMF, 25 °C, 2 h, 76%; (c) TFA/H2O 8/2, 25 °C, 3 h, 76% for 1 and 34% for 9; (d) (i) 21, AcOH, CH2Cl2, 25 °C, 2 h, (ii) NaBH(OAc)3, 25 °C, 2 h, 93%; (e) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 2 M aqueous solution LiOH, 25 °C, 0.5 h, 32%; (f) TFA/H2O 8/2, 25 °C, 3 h, 35%; (g) (i) TFA/H2O 8/2, 25 °C, 3 h, (ii) 7 M NH3/MeOH, 30 °C, 24 h, 38%; (h) 1-bromobutane, DIEA, NMP, microwave 110 °C, 4 h, 47% for 23; 1-bromo-3-phenylpropane, DIEA, NMP, microwave 110 °C, 4 h, 53% for 24, methyl 4-bromobutyrate, DIEA, NMP, microwave 110 °C, 3.5 h, 58% for 25; (i) (i) TFA/H2O 8/2, 25 °C, 6 h, 72% for 5; 3 h, 28% for 6; 5.5 h, 60% for 7; 5.5 h for 8. (ii) 2 M aqueous solution LiOH, 0 °C, 0.5 h, 36% for 8."}