Homo Dinucleoside-α-hydroxyphosphonate Diesters as Prodrugs of the Antiviral Nucleoside Analogues 2′,3′-Dideoxythymidine and 3′-Azido-2′,3′-dideoxythymidine

Chris Meier Institute of Organic Chemistry, University of Frankfurt, Marie-Curie-Str. 11, D-60439, Frankfurt/Main, Germany

Lothar Habel Institute of Organic Chemistry, University of Frankfurt, Marie-Curie-Str. 11, D-60439, Frankfurt/Main, Germany

Wolfgang Laux Institute of Organic Chemistry, University of Frankfurt, Marie-Curie-Str. 11, D-60439, Frankfurt/Main, Germany

Erik De Clercq Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

Jan Balzarini Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000, Leuven, Belgium

Abstract

The synthesis of a new prodrug system for antiviral nucleosides AZT (1) and ddT (2) based on α-hydroxybenzylphosphonates 3 is described. 3 hydrolyze via different mechanisms yielding the H-phosphonate monoesters 4 or nucleoside monophosphates 5, respectively. 3 were more lipophilic than 1, 2 and showed marked activity against HIV-1/2.

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Homo Dinucleoside-α-hydroxyphosphonate Diesters as Prodrugs of the Antiviral Nucleoside Analogues 2′,3′-Dideoxythymidine and 3′-Azido-2′,3′-dideoxythymidine

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Homo Dinucleoside-α-hydroxyphosphonate Diesters as Prodrugs of the Antiviral Nucleoside Analogues 2′,3′-Dideoxythymidine and 3′-Azido-2′,3′-dideoxythymidine

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