1,7-DIDEAZA-2',3'-DIDEOXYADENOSINE - SYNTHESES OF PYRROLO[2,3-B]PYRIDINE 2',3'-DIDEOXYRIBOFURANOSIDES AND PARTICIPATION OF PURINE N(1) DURING HIV-1 REVERSE-TRANSCRIPTASE INHIBITION
DC Element | Wert | Sprache |
---|---|---|
dc.contributor.author | SEELA, F | |
dc.contributor.author | GUMBIOWSKI, R | |
dc.date.accessioned | 2021-12-23T15:58:50Z | - |
dc.date.available | 2021-12-23T15:58:50Z | - |
dc.date.issued | 1991 | |
dc.identifier.issn | 0018019X | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/3590 | - |
dc.description.abstract | The syntheses of 1,7-dideaza-2',3'-dideoxyadenosine (1) and related pyrrolo[2,3-b]pyridine 2',3'-dideoxyribo- and 2',3'-didehydro-2',3'-dideoxyribonucleosides (see 2-5) are described. As starting materials, 2'-deoxyribonucleosides 6 or 7 were used. The 3'-OH group was removed by Barton deoxygenation or via mesylation followed by elimination and catalytic hydrogenation. Compound 1 was also obtained from the direct glycosylation of 4-nitro-H-1-pyrrolo[2,3-b]pyridine (17) with the 2,3-dideoxyribofuranosyl chloride 18. The triphosphate 25 of 1 showed only marginal activity against HIV-1 reverse transcriptase, indicating that purine N(1) is required for the inhibitory activity of the parent 2',3'-dideoxyadenosine. | |
dc.language.iso | en | |
dc.publisher | NEW SWISS CHEMICAL SOC | |
dc.relation.ispartof | HELVETICA CHIMICA ACTA | |
dc.subject | 2',3'-DIDEOXYRIBONUCLEOSIDES | |
dc.subject | ACID | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Multidisciplinary | |
dc.subject | NUCLEOBASE ANION | |
dc.subject | PHASE-TRANSFER GLYCOSYLATION | |
dc.subject | RIBONUCLEOSIDES | |
dc.title | 1,7-DIDEAZA-2',3'-DIDEOXYADENOSINE - SYNTHESES OF PYRROLO[2,3-B]PYRIDINE 2',3'-DIDEOXYRIBOFURANOSIDES AND PARTICIPATION OF PURINE N(1) DURING HIV-1 REVERSE-TRANSCRIPTASE INHIBITION | |
dc.type | journal article | |
dc.identifier.doi | 10.1002/hlca.19910740514 | |
dc.identifier.isi | ISI:A1991GB04700013 | |
dc.description.volume | 74 | |
dc.description.issue | 5 | |
dc.description.startpage | 1048 | |
dc.description.endpage | 1058 | |
dc.publisher.place | VERLAG HELVETICA CHIMICA ACTA, MALZGASSE 21, POSTFACH 313, CH-4010 BASEL, SWITZERLAND | |
dcterms.isPartOf.abbreviation | Helv. Chim. Acta |
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