Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity

Eur J Med Chem. 2007 Jul;42(7):934-9. doi: 10.1016/j.ejmech.2006.12.032. Epub 2007 Jan 14.

Abstract

3-(1,3-diphenylpyrazol-4-yl-methylene)-5-aryl-2(3H)-furanones 2 were prepared and converted into a variety of heterocyclic systems of synthetic and biological importance. Benzylamine reacted with the furanones 2; the product was found to depend on the reaction conditions. Thus, at room temperature the open-chain N-benzylamides 3 were obtained, whereas under refluxing conditions the 2(3H)-pyrrolones were obtained. Hydrazine hydrate affected ring opening of the furanones to give the corresponding acid hydrazides 5. The latter products were used as key starting materials for the synthesis of pyridazinones 7 and 8, 1,3,4-oxadiazoles 11 and 13 and 1,2,4-triazoles 12 and 14 all bearing pyrazolyl moiety as a side-chain. Evaluation of antiviral activity of selected examples of the compounds obtained was performed using two viruses: HAV and HSV-1. Some of the tested compounds showed promising activities.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Chlorocebus aethiops
  • Furans / chemistry*
  • Furans / pharmacology
  • Hepatitis A virus / drug effects
  • Herpesvirus 1, Human / drug effects
  • Molecular Structure
  • Vero Cells
  • Viral Plaque Assay

Substances

  • Antiviral Agents
  • Furans