1,3,4-Oxadiazole-3(2H)-carboxamide derivatives as potential novel class of monoamine oxidase (MAO) inhibitors: synthesis, evaluation, and role of urea moiety

Bioorg Med Chem. 2008 Aug 15;16(16):7565-72. doi: 10.1016/j.bmc.2008.07.026. Epub 2008 Jul 18.

Abstract

A new series of 1,3,4-oxadiazole-3(2H)-carboxamide derivatives have been synthesized by direct heterocyclization reaction of substituted benzoylisocyanate with various aroylhydrazones as novel monoamine oxidase inhibitors (MAOIs). The target molecules have been identified on the basis of satisfactory analytical and spectra (IR, (1)H NMR, (13)C NMR, and HR-MS) data. The newly synthesized compounds were evaluated for their MAO inhibitory activity by kynuramine fluorimetric assay method. The preliminary results showed that most of the compounds have moderate inhibitory activities toward MAO at the concentration of 10(-5)-10(-3)M. This work may provide a novel class of lead compounds with potential MAO inhibitions for further optimization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mitochondria / metabolism
  • Monoamine Oxidase / chemistry
  • Monoamine Oxidase / metabolism
  • Monoamine Oxidase Inhibitors / chemical synthesis*
  • Monoamine Oxidase Inhibitors / chemistry
  • Monoamine Oxidase Inhibitors / pharmacology*
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology*
  • Rats
  • Spectrophotometry, Infrared
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis
  • Urea / pharmacology

Substances

  • Monoamine Oxidase Inhibitors
  • Oxadiazoles
  • Urea
  • Monoamine Oxidase