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Synthesis of unnatural 3′-phospha-2′-deoxyfuranose nucleoside analogues |
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| Authors: | Bénédicte Dayde Claire Pierra Gilles Gosselin Dominique Surleraux Amadou Tidjani Ilagouma Jean-Noël Volle David Virieux Jean-Luc Pirat |
| Institution: | 1. AM2N, Institut Charles Gerhardt, UMR 5253, ENSCM, 8, rue de l’Ecole Normale, 34296 Montpellier, France;2. Idenix Pharmaceuticals, Medicinal Chemistry Laboratory, Cap Gamma, 1682 rue de la Valsière, BP50001, 34189 Montpellier Cedex 4, France;3. Institut des biomolécules Max Mousseron (IBMM), UMR 5247 CNRS-UM1-UM2, Université Montpellier 2, cc1705, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France;4. Département de Chimie, Faculté des Sciences, Université Abdou Moumouni, B.P. 10662 Niamey, Niger |
| Abstract: | This Letter describes the synthesis of racemic analogues of unnatural 2′-deoxy nucleoside with a phosphorus atom replacing the carbon atom in the 3′-position. A seven-step sequence was developed in racemic series to afford unnatural 3′-phospha-2′-deoxyfuranose nucleosides. The phospha nucleoside analogues were tested against HCV, but did not show any antiviral activity at a 10 μM maximum concentration used for the inhibition assays of analogues 2-T, 2-C and 4-Tα. |
| Keywords: | Deoxy nucleosides analogues Pudovik reaction P-alkylation reaction Radical deiodination |
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