Synthesis and antiviral activity of 3'-heterocyclic substituted 3'-deoxythymidines |
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| Authors: | P Wigerinck A Van Aerschot G Janssen P Claes J Balzarini E De Clercq P Herdewijn |
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| Affiliation: | Rega Institute for Medical Research, Katholieke Universiteit Leuven, Belgium. |
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| 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. |
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