Synthesis and Antiviral Evaluation of Hydantoin Analogues of AZT

Abstract

3′‐Azidonucleosides 4 have been synthesized by condensation of silylated (Z)‐5‐ethylidenehydantoin and (Z)‐5‐benzylidenehydantoin with methyl 3‐azido‐5‐O‐tert‐butyldiphenylsilyl‐2,3‐dideoxy‐D‐erythro‐pentofuranoside (3). The nucleosides 4 were deblocked on treatment with tetrabutylammonium fluoride. The ethylidene group isomerized from Z to E configuration during the nucleoside synthesis. The new nucleosides did not show any appreciable activities against HIV‐1 or HSV‐1. Copyright © 1994 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim