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

Autor(en): SEELA, F
GUMBIOWSKI, R
Stichwörter: 2',3'-DIDEOXYRIBONUCLEOSIDES; ACID; Chemistry; Chemistry, Multidisciplinary; NUCLEOBASE ANION; PHASE-TRANSFER GLYCOSYLATION; RIBONUCLEOSIDES
Erscheinungsdatum: 1991
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 74
Ausgabe: 5
Startseite: 1048
Seitenende: 1058
Zusammenfassung: 
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.
ISSN: 0018019X
DOI: 10.1002/hlca.19910740514

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