Stereoselective synthesis and anti-HCV activity of conformationally restricted 2′-C-substituted carbanucleosides

Won Jun Choi, Yun Jung Ko, Girish Chandra, Hyuk Woo Lee, Hea Ok Kim, Hyo Jung Koh, Hyung Ryong Moon, Young Hoon Jung, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

Conformationally restricted 2′-C-azido-, hydroxy- and fluoromethyl-carbanucleosides 4b-f were efficiently synthesized via the stereoselective conversion of ketone 7 to epoxide 14, followed by the stereoselective opening of the epoxide with nucleophiles (OAc, N 3, and F), while the corresponding 2′-C-methyl-carbanucleoside 4a was synthesized via the stereoselective Grignard reaction of ketone 7 with methylmagnesium iodide as a key step. All the final nucleosides 4a-f were assayed for anti-HCV activity, but showed neither significant anti-HCV activity nor cytotoxicity in a cell-based replicon assay.

Original languageEnglish
Pages (from-to)1253-1261
Number of pages9
JournalTetrahedron
Volume68
Issue number4
DOIs
StatePublished - 28 Jan 2012

Keywords

  • Anti-HCV activity
  • Carbocyclic nucleosides
  • Cyclic sulfate
  • Stereoselective epoxidation
  • Sulfur ylide

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