Issue 17, 2012
From the journal:

Organic & Biomolecular Chemistry

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  

* 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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Article information

DOI
https://doi.org/10.1039/C2OB25131K
Article type
Paper
Submitted
17 Jan 2012
Accepted
29 Feb 2012
First published
29 Feb 2012

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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