Acyclic analogs of 3'-azido-3'-deoxythymidine as potential antiviral agents. Nucleoside synthesis by Michael addition

P Scheiner, A Geer, AM Bucknor…

Index: Scheiner; Geer; Bucknor; Imbach; Schinazi Journal of Medicinal Chemistry, 1989 , vol. 32, # 1 p. 73 - 76

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Citation Number: 52

Abstract

An acyclic derivative of 3'-azido-3'-deoxythymidine,(R, S)-l-[l-(2-hydroxyethoxy)-3- azidopropyl] thymine (2), has been synthesized by a path involving Michael-type addition. Related thymidine analogues lacking the C (3')-C (4') bond were similarly obtained. The method provides a versatile new route to nucleoside analogues. The new compounds were found to be essentially inactive against human immunodeficiency virus type 1 (HIV-1) and ...