Synthesis and antiviral evaluation of novel 5-(N-Aryl-aminomethyl-1,3,4-oxadiazol-2-yl)hydrazines and their sugars, 1,2,4-triazoles, tetrazoles and pyrazolyl derivatives

Arch Pharm (Weinheim). 2008 May;341(5):307-13. doi: 10.1002/ardp.200700154.

Abstract

A number of new N-arylaminomethyl-1,3,4-oxadiazole derivatives 2, 3a,b, and 9-12a,b were prepared. Sugar (5-N-arylaminomethyl-1,3,4-oxadiazol-2-yl) hydrazones 4-6a,b were synthesized by the reaction of the hydrazino derivatives 3a,b with the corresponding monosaccharides. The novel acyclo-C-nucleosides 7, 8a,b were prepared by heterocyclization of the sugar hydrazones 4, 5a,b with acetic anhydride. A number of the synthesized compounds were tested for their antiviral activity against herpes simplex virus type-1 (HSV-1) and hepatitis-A virus (HAV, MBBcell culture-adapted strain). The results revealed that the sugar hydrazones 6a,b showed higher antiviral activity compared to the other hydrazones and their acetylated derivatives.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Hydrazines / chemical synthesis*
  • Hydrazines / pharmacology
  • Pyrazoles / chemical synthesis
  • Pyrazoles / pharmacology
  • Tetrazoles / chemical synthesis*
  • Tetrazoles / pharmacology
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology

Substances

  • Antiviral Agents
  • Hydrazines
  • Pyrazoles
  • Tetrazoles
  • Triazoles