Fluorescent tricyclic analogues of acyclovir and ganciclovir. A structure-antiviral activity study

J Med Chem. 2001 Nov 22;44(24):4284-7. doi: 10.1021/jm010922s.

Abstract

Of a series of new guanine base modified tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system, evaluated for activity against herpes simplex virus type 1 and 2, several fluorescent analogues, 6-(4-MeOPh)-TACV (8), 7-Me-6-Ph-TACV (17), 6-(4-MeOPh)-TGCV (27), and 7-Me-6-Ph-TGCV (28), were obtained that showed similar potency and selectivity as the parent compounds. The activity was found to be strongly dependent on the nature and steric demands of the substituents in the 6 and/or 7 position.

MeSH terms

  • Acyclovir / analogs & derivatives*
  • Acyclovir / chemical synthesis*
  • Acyclovir / chemistry
  • Acyclovir / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Cell Line
  • Cytopathogenic Effect, Viral
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology
  • Ganciclovir / analogs & derivatives*
  • Ganciclovir / chemical synthesis*
  • Ganciclovir / chemistry
  • Ganciclovir / pharmacology
  • Herpesvirus 1, Human / drug effects
  • Herpesvirus 2, Human / drug effects
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Fluorescent Dyes
  • Ganciclovir
  • Acyclovir