Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines.

Abstract:

:Various 3'-deoxythymidine analogues with an heterocyclic five-membered ring in the 3'-erythro position have been synthesized. The pyrrol-1-yl (3) and the 1,2,4-triazol-4-yl (5) compounds were synthesized from 1-(3-amino-2,3-dideoxy-beta-D-erythro-pentofuranosyl)thymine. The pyrazol-1-yl (16a), imidazol-1-yl (16b), and 1,2,4-triazol-1-yl (16c) derivatives were obtained by epoxide opening of the corresponding 1-(2,3-anhydro-beta-D-lyxofuranosyl)thymines followed by 2'-deoxygenation. Only the 3'-pyrrol-1-yl derivative showed marginal antiviral activity against human immunodeficiency virus.

journal_name

J Med Chem

authors

Wigerinck P,Van Aerschot A,Janssen G,Claes P,Balzarini J,De Clercq E,Herdewijn P

doi

10.1021/jm00164a063

subject

Has Abstract

pub_date

1990-02-01 00:00:00

pages

868-73

issue

2

eissn

0022-2623

issn

1520-4804

journal_volume

33

pub_type

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