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

  • Choi W
  • Ko Y
  • Chandra G
 et al. 
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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, N3, 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. © 2011 Elsevier Ltd. All rights reserved.

Author-supplied keywords

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

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Authors

  • Won Jun Choi

  • Yun Jung Ko

  • Girish Chandra

  • Hyuk Woo Lee

  • Hea Ok Kim

  • Hyo Jung Koh

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