Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines
- 1 February 1990
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 33 (2) , 868-873
- https://doi.org/10.1021/jm00164a063
Abstract
Various 3''-deoxythymidine analogoues with an heterocyclic five-membered ring 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.This publication has 4 references indexed in Scilit:
- Anti-retrovirus activity of 3′-fluoro- and 3′-azido-substituted pyrimidine 2′,3′-dideoxynucleoside analoguesBiochemical Pharmacology, 1988
- Azidothymidine: crystal structure and possible functional role of the azido group.Proceedings of the National Academy of Sciences, 1987
- Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virusCanadian Journal of Chemistry, 1987
- Synthesis and biological activity of several amino analogs of thymidineJournal of Medicinal Chemistry, 1978