Synthesis and anti-hepatitis C virus (HCV) activity of 3'-C-substituted-methyl pyrimidine and purine nucleosides

Bioorganic & Medicinal Chemistry
Won Jun ChoiLak Shin Jeong

Abstract

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.

References

Sep 26, 1997·Hepatology : Official Journal of the American Association for the Study of Liver Diseases·J H Hoofnagle
Oct 8, 2003·Current Drug Targets. Infectious Disorders·G Lake-Bakaar
Sep 11, 2007·Advanced Drug Delivery Reviews·Tetsuro SuzukiTakaji Wakita
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