Synthesis of new series of quinoxaline based MAO-inhibitors and docking studies

Eur J Med Chem. 2010 Oct;45(10):4479-89. doi: 10.1016/j.ejmech.2010.07.008. Epub 2010 Jul 21.

Abstract

A series of 2-benzyl-3-(2-arylidenehydrazinyl)quinoxalines 3, 4-benzyl-1-aryl-[1,2,4]triazolo[4,3-a]quinoxalines 4 and phenyl(1-aryl-[1,2,4]triazolo[4,3-a]quinoxalin-4-yl)methanones 5 analogues were synthesized and investigated for their monoamine oxidase (MAO) inhibitory property. The inhibition profile was found to be competitive for compounds 3k, 3m, 5f and 5n with MAO-A selectivity. Observation of the docked positions of these compounds revealed interactions with many residues previously reported to have an effect on the inhibition of the enzyme. The structural features of the new compounds have been determined from the microanalytical, IR, (1)H, (13)C NMR spectral studies and X-ray crystalography.

MeSH terms

  • Animals
  • Cattle
  • Crystallography, X-Ray
  • Humans
  • Male
  • Mice
  • Mitochondria / enzymology
  • Models, Molecular
  • Monoamine Oxidase / chemistry
  • Monoamine Oxidase / metabolism*
  • Monoamine Oxidase Inhibitors / adverse effects
  • Monoamine Oxidase Inhibitors / chemical synthesis
  • Monoamine Oxidase Inhibitors / chemistry*
  • Monoamine Oxidase Inhibitors / pharmacology*
  • Protein Binding
  • Quinoxalines / adverse effects
  • Quinoxalines / chemical synthesis
  • Quinoxalines / chemistry*
  • Quinoxalines / pharmacology*
  • Rats

Substances

  • Monoamine Oxidase Inhibitors
  • Quinoxalines
  • Monoamine Oxidase