Synthesis and Antiviral Activity of 3'-Heterocyclic Substituted 3'-Deoxythymidines

Article abstract of DOI:10.1021/jm00164a063

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-β-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-β-D-lyxofuranosyl)thymines followed by 2'-deoxygenation.Only the 3'-pyrrol-1-yl derivative showed marginal antiviral activity against human immunodeficiency virus.