Synthesis and anti-hepatitis C virus (HCV) activity of 3'-C-substituted-methyl pyrimidine and purine nucleosides.
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On the basis of potent anti-hepatitis C virus (HCV) activity of 2'-C-hydroxymethyladenosine, 3'-C-substituted-methyl-ribofuranosyl pyrimidine and purine nucleosides were designed and synthesized from D-xylose. Among compounds tested, all adenine analogues, 4a, 4d, and 4g showed significant anti-HCV activity in a replicon-based cell assay irrespective of the substituent (Y=OH, N₃, or F) at the 3'-C-substituted methyl position, among which 4g (Y=N₃) was the most potent, but it is also cytotoxic. This study guarantees the 3'-C-substituted-methyl nucleoside serves as a new template for the development of new anti-HCV agents.