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Issue 17, 2012
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Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states

Bénédicte Dayde,ab  Samira Benzaria,b  Claire Pierra,b  Gilles Gosselin,bc  Dominique Surleraux,b  Jean-Noël Volle,a  Jean-Luc Pirata  and  David Virieux*a 
Author affiliations

* Corresponding authors

a AM2N, Institut Charles Gerhardt, UMR 5253, ENSCM, 8 rue de l'Ecole Normale, F-34296 Montpellier, France
E-mail: david.virieux@enscm.fr
Fax: +33 (0)467 14 43 19
Tel: +33 (0)467 14 43 14

b Idenix Pharmaceuticals, Medicinal Chemistry Laboratory, Cap Gamma, 1682 rue de la Valsière, BP50001, 34189 Montpellier Cedex 4, France

c UMR5247 CNRS-UM1-UM2 (IBMM), Université Montpellier 2, 34095 Montpellier Cedex 5, France

Abstract

A 6-step procedure was developed for the synthesis of a new family of acyclic nucleoside phosphonates (ANPs), “PHEEPA” [(2-pyrimidinyl-2-(2-hydroxyethoxy)ethyl)phosphonic acids] in overall yields ranging from 4.5% to 32%. These compounds, which possess on one side a hydroxy function and on the other side a phosphonate group, can be considered either as potential antiviral agents or as transition state analogues of nucleoside phosphorylases such as thymidine phosphorylase.

Graphical abstract: Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states

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Publication details

The article was received on 17 Jan 2012, accepted on 29 Feb 2012 and first published on 29 Feb 2012


Article type: Paper
DOI: 10.1039/C2OB25131K
Citation: Org. Biomol. Chem., 2012,10, 3448-3454
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    Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states

    B. Dayde, S. Benzaria, C. Pierra, G. Gosselin, D. Surleraux, J. Volle, J. Pirat and D. Virieux, Org. Biomol. Chem., 2012, 10, 3448
    DOI: 10.1039/C2OB25131K

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