Synthesis and antiviral activity of 1-(2-deoxy-beta-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone

J Med Chem. 1981 Jan;24(1):109-12. doi: 10.1021/jm00133a022.

Abstract

1-(2-Deoxy-beta-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone (1b) was synthesized via modification of the silyl method. 1b inhibits the Herpes simplex virus type 1 (98%) and type 2 (97%) at a concentration which is nontoxic to human HeLa cells. The compound shows 50 times greater binding affinity (lower Ki) to the virus-specific thymidine kinase than to the thymidine kinase of uninfected HeLa cells.

Publication types

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

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / metabolism
  • Chemical Phenomena
  • Chemistry
  • Humans
  • Simplexvirus / drug effects
  • Thionucleosides / chemical synthesis*
  • Thionucleosides / pharmacology
  • Thymidine Kinase / metabolism
  • Viral Plaque Assay

Substances

  • Antiviral Agents
  • Thionucleosides
  • 1-(2-deoxy-beta-D-ribofuranosyl)-5-(methylmercapto)-2-pyrimidinone
  • Thymidine Kinase