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

Bénédicte Dayde (1) , Samira Benzaria (2) , Claire Pierra (2) , Gilles Gosselin (3) , Dominique Surleraux (2) , Jean-Noël Volle (1) , Jean-Luc Pirat (1) , David Virieux (1)

1 ICGM ICMMM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
2 Idenix Pharmaceuticals
3 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

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.

Domaines: Chimie organique

Bénédicte Dayde, Samira Benzaria, Claire Pierra, Gilles Gosselin, Dominique Surleraux, et al.. Synthesis of a new family of acyclic nucleoside phosphonates, analogues of TPases transition states. Organic & Biomolecular Chemistry, 2012, 10, pp.3448-3454. ⟨10.1039/c2ob25131k⟩. ⟨hal-00993912⟩