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

Won Jun Choi, Yu Min Kim, Hea Ok Kim, Hyuk Woo Lee, Dong Eun Kim, Kwang Su Park, Youhoon Chong, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

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.

Original languageEnglish
Pages (from-to)4812-4820
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number13
DOIs
StatePublished - 2010
Externally publishedYes

Keywords

  • 3′-C-Azidomethyl nucleosides
  • 3′-C-Fluoromethyl nucleosides
  • 3′-C-Hydroxymethyl nucleosides
  • Anti-hepatitis C virus (HCV) activity
  • Neighboring group effect

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