Conversion of 3-arylazo-5-phenyl-2(3H)-furanones into other heterocycles of anticipated biological activity

Arch Pharm (Weinheim). 2007 Jun;340(6):315-9. doi: 10.1002/ardp.200700043.

Abstract

3-arylazo-5-phenyl-2(3H)-furanones 3 were prepared and converted into a variety of heterocyclic systems of synthetic and biological importance. Hydrazine hydrate reacted with furanones as nucleophiles and gave the corresponding acid hydrazides 4. The latter products were used as starting materials for the synthesis of 1,3,4-oxadiazoles 6, 9, and the 1,2,4-triazoles 8. Evaluation of the antiviral activity of selected compounds obtained was performed using two viruses: HAV and HSV-1. Some of the tested compounds showed promising activities.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / pharmacology
  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Azo Compounds / chemical synthesis*
  • Azo Compounds / chemistry
  • Azo Compounds / pharmacology*
  • Chemistry, Pharmaceutical / methods*
  • Chlorocebus aethiops
  • Furans / chemistry*
  • Hepatitis A virus / drug effects
  • Herpesvirus 1, Human / drug effects
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology*
  • Molecular Structure
  • Vero Cells

Substances

  • Antiviral Agents
  • Azo Compounds
  • Furans
  • Heterocyclic Compounds
  • 4-Butyrolactone