Synthesis and Anti-Retroviral Activity of O,O′-BIS(3′-Azido-2′,3′-Dideoxythymidin-5′-yl) Phosphoramidate Derivatives

Inger Kers Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91, Stockholm, Sweden

Jacek Stawiński Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91, Stockholm, Sweden

Jean-Luc Girardet Laboratoire de Chimie Bioorganique, UMR CNRS 5625, Universite Montpellier II, 34095, Montpellier, Cedex, 5, France

Jean-Louis Imbach Laboratoire de Chimie Bioorganique, UMR CNRS 5625, Universite Montpellier II, 34095, Montpellier, Cedex, 5, France

Christian Perigaud Laboratoire de Chimie Bioorganique, UMR CNRS 5625, Universite Montpellier II, 34095, Montpellier, Cedex, 5, France

Gilles Gosselin Laboratoire de Chimie Bioorganique, UMR CNRS 5625, Universite Montpellier II, 34095, Montpellier, Cedex, 5, France

Anne-Marie Aubertin Institut de Virologie de la Faculté de Médecine de Strasbourg, Unité INSERM 74, 3 rue de Koberlé, 67000, Strasbourg, France

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Abstract

A simple and efficient protocol for the preparation of various symmetrical dinucleoside phosphoramidates derived from AZT, is presented. It consists of the phosphonylation of AZT with phosphonic acid in the presence of DCC to produce the symmetrical H-phosphonate diester, followed by its oxidative conversion to various phosphoramidate analogues. The synthesized compounds were evaluated for their anti-HIV activity in different cell cultures.

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Synthesis and Anti-Retroviral Activity of O,O′-BIS(3′-Azido-2′,3′-Dideoxythymidin-5′-yl) Phosphoramidate Derivatives

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Synthesis and Anti-Retroviral Activity of O,O′-BIS(3′-Azido-2′,3′-Dideoxythymidin-5′-yl) Phosphoramidate Derivatives

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