Synthesis and Evaluation of Human Monoamine Oxidase Inhibitory Activities of Some 3,5-Diaryl-N-substituted-4,5-dihydro-1H-pyrazole-1-carbothioamide Derivatives

Senturk K., Tan O., Ciftci S. Y., UÇAR G., PALASKA E.

ARCHIV DER PHARMAZIE, vol.345, no.9, pp.695-702, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 345 Issue: 9
  • Publication Date: 2012
  • Doi Number: 10.1002/ardp.201100448
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.695-702
  • Keywords: 2-Pyrazoline, 4, 5-Dihydropyrazole, Docking, Monoamine oxidase, 1-ACETYL-3,5-DIPHENYL-4,5-DIHYDRO-(1H)-PYRAZOLE DERIVATIVES, REVERSIBLE INHIBITORS, BEFLOXATONE, DOCKING
  • Hacettepe University Affiliated: Yes

Abstract

Sixteen 3-aryl-5-(4-fluorophenyl)-N-substituted-4,5-dihydro-1H-pyrazole-1-carbothioamide derivatives were synthesized and their structure were identified by UV, IR, 1H NMR, mass spectra, and microanalyses. The compounds were evaluated in vitro for their human monoamine oxidase (hMAO) inhibitory activities and their MAO-A and -B selectivity. All the compounds were found to potently inhibit MAO-A isoforms. 5-(4-Fluorophenyl)-3-(4-methoxyphenyl)-N-methyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (1.0?x?10-3?mu M) was found to inhibit hMAO-A most selectively and potently. The binding mode of 5-(4-fluorophenyl)-3-(4-methoxyphenyl)-N-methyl-4,5-dihydro-1H-pyrazole-1-carbothioamide to hMAO-A was also predicted using docking studies.