Regioselective synthesis of 6-substituted-2-amino-5-bromo-4(3H)-pyrimidinones and evaluation of their antiviral activity

Eur J Med Chem. 2013 Sep:67:428-33. doi: 10.1016/j.ejmech.2013.06.036. Epub 2013 Jul 5.

Abstract

A series of 2-amino-5-bromo-4(3H)-pyrimidinone derivatives bearing different substituents at the C-6 position were synthesized using a highly regioselective lithiation-substitution protocol, and the effect of structural variation at the C-6 position on their antiviral activity in cell culture was evaluated. Although some of the derivatives were found to be active against various virus strains, they were effective only close to their toxicity threshold.

Keywords: Antiviral; Cytotoxicity; Interferon inducers; Lithiation; Pyrimidinone; Regioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cells, Cultured
  • Chlorocebus aethiops
  • Dogs
  • Dose-Response Relationship, Drug
  • HeLa Cells
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry
  • Pyrimidinones / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Vero Cells
  • Viruses / drug effects*

Substances

  • 2-amino-5-bromo-4(3H)-pyrimidinone
  • Antiviral Agents
  • Pyrimidinones