Synthesis of benzodithiol-2-yl-substituted nucleoside derivatives as lead compounds having anti-bovine viral diarrhea virus activity

J Med Chem. 2004 Oct 7;47(21):5265-75. doi: 10.1021/jm049677d.

Abstract

Nucleoside derivatives having a benzodithiol-2-yl (BDT) group were synthesized and examined for their anti-bovine viral diarrhea virus (BVDV) activities. Other substituents structurally similar to the BDT group such as 1,3-benzodioxol-2-yl, benzimidazol-2-yl and 1-oxo-benzodithiol-2-yl groups were not effective as the pharmacophore. The anti-BVDV assay revealed that 2'-O-BDT-guanosine and 2'-O-BDT-inosine had the strongest anti-BVDV activity among the nucleoside derivatives synthesized in this study. Since BVDV has been recognized as a surrogate for human hepatitis C virus (HCV), the BDT-modified nucleosides might become a new class of lead compounds to find nucleoside-type anti-HCV agents such as ribavirin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Biological Assay / methods
  • Cattle
  • Diarrhea Viruses, Bovine Viral / drug effects*
  • Hepacivirus / drug effects
  • Humans
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleosides / pharmacology
  • Structure-Activity Relationship
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry
  • Sulfhydryl Compounds / pharmacology
  • Virology / methods

Substances

  • Antiviral Agents
  • Nucleosides
  • Sulfhydryl Compounds