Synthesis and study of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides as structural analogues of (S)-HPMPC (cidofovir). - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue New Journal of Chemistry Année : 2014

Synthesis and study of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides as structural analogues of (S)-HPMPC (cidofovir).

Résumé

A synthetic pathway to new acyclonucleoside phosphonates, designed as analogues of cidofovir, is described. The reduction of a β-ketophosphonate intermediate, readily available from the nucleobase and benzylacrylate, afforded an enantiomeric mixture of (R)- and (S)-β-hydroxyphosphonate derivatives which was resolved. The assignment of the absolute configuration was proposed on the basis of NMR studies. The influence of this modification, the presence of the hydroxyl group and chirality on the β-position related to the phosphorus atom, on antiviral activity against a broad variety of DNA and RNA viruses and also on the capacity to be recognized as substrates by human NMP kinases was investigated.

Domaines

Chimie organique
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Dates et versions

hal-01078468 , version 1 (29-10-2014)

Identifiants

Citer

Mahesh Kasthuri, Chahrazade El Amri, Valérie Lefort, Christian Périgaud, Suzanne Peyrottes. Synthesis and study of (R)- and (S)-β-hydroxyphosphonate acyclonucleosides as structural analogues of (S)-HPMPC (cidofovir).. New Journal of Chemistry, 2014, 38 (10), pp.4736-4742. ⟨10.1039/c4nj00813h⟩. ⟨hal-01078468⟩
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