Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox)

Bioorg Med Chem Lett. 2003 Jan 6;13(1):9-12. doi: 10.1016/s0960-894x(02)00841-7.

Abstract

An improved method for the synthesis of enantiomerically pure D-cyclopentenyl nucleosides has been accomplished and their antiviral activity against orthopox viruses have been evaluated. The key intermediate, L-cyclopent-2-enone 13 was prepared from D-ribose using a ring closing metathesis reaction in eight steps. Among the synthesized nucleosides, the adenine 2 (Neplanocin A), cytosine 14, and 5-F-cytosine 15 analogues exhibited potent anti-orthopox virus activity, including smallpox virus.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / pharmacology
  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Cell Line
  • Cell Survival / drug effects
  • Cowpox virus / drug effects
  • Cytidine / analogs & derivatives*
  • Cytidine / chemical synthesis
  • Cytidine / pharmacology
  • Monkeypox virus / drug effects
  • Nucleosides / chemical synthesis*
  • Nucleosides / pharmacology
  • Orthopoxvirus / drug effects*
  • Structure-Activity Relationship
  • Variola virus / drug effects

Substances

  • Antiviral Agents
  • Nucleosides
  • Cytidine
  • cyclopentenyl cytosine
  • neplanocin A
  • Adenosine