Collect. Czech. Chem. Commun. 2006, 71, 991-1010

Synthesis of 2'-C-Methylcytidine and 2'-C-Methyluridine Derivatives Modified in the 3'-Position as Potential Antiviral Agents

Claire Pierraa, Agnès Amadorb, Eric Badarouxa, Richard Storerb and Gilles Gosselina,*

a Laboratoire Coopératif Idenix-CNRS-Université Montpellier II, Université Montpellier II, case courrier 008, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France
b Laboratoires Idenix SARL, Laboratoire de Chimie Médicinale, Cap Gamma, 1682 Rue de la Valsiere, BP 50001, 34189 Montpellier Cedex 4, France


As part of our anti-hepatitis C program, we recently discovered 2'-C-methylcytidine (1) and 2'-C-methyluridine (2), which are potent inhibitors in cell culture of several viruses (bovine viral diarrhea virus (BVDV), yellow fever virus (YFV)) closely related to HCV. In order to characterize structure-activity relationships, we introduced some structural and functional modifications into the 3'-position of 2'-C-methylcytidine and 2'-C-methyluridine. All these hitherto unknown compounds thus synthesized were tested for the activity against a wide range of viruses and found to be inactive.

Keywords: Pyrimidines; Antivirals; Hepatitis C virus; 2'-C-Methyl branched ribonucleosides; Deoxygenation; Fluorination; RNA viruses; Nucleosides.

References: 29 live references.