Synthesis and Screening of Human Monoamine Oxidase-A Inhibitor Effect of New 2-Pyrazoline and Hydrazone Derivatives

EVRANOS-AKSOZ B., BAYSAL İ. , Yabanoglu-Ciftci S. , Djikic T., Yelekci K., UÇAR G. , ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.348, ss.743-756, 2015 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 348 Konu: 10
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1002/ardp.201500212
  • Sayfa Sayıları: ss.743-756


A group of 3,5-diaryl-2-pyrazoline and hydrazone derivatives was prepared via the reaction of various chalcones with hydrazide compounds in ethanol. Twenty original compounds were synthesized. Ten of these original compounds have a pyrazoline structure, nine of these original compounds have a hydrazone structure, and one of these original compounds has a chalcone structure. Structural elucidation of the compounds was performed by IR, H-1 NMR, C-13 NMR, mass spectral data, and elemental analyses. These compounds were tested for their inhibitory activities toward the A and B isoforms of human monoamine oxidase (MAO). Except for 3k and 6c, all compounds were found to be competitive, reversible, and selective inhibitors for either one of the isoforms (hMAO-A or MAO-B). Compounds 3k and 6c were found to be competitive, reversible, but non-selective MAO inhibitors. Compound 6h showed hMAO-B inhibitory activity whereas the others potently inhibited hMAO-A. Compound 5c showed higher selectivity than the standard drug moclobemide. According to the experimental K-i values, compounds 6i, 6d, and 6a exhibited the highest inhibitory activity toward hMAO-A. The AutoDock 4.2 program was employed to perform automated molecular docking. The calculated results obtained computationally were in good agreement with the experimental values.