Premium
Synthesis and Evaluation of Human Monoamine Oxidase Inhibitory Activities of Some 3,5‐Diaryl‐ N ‐substituted‐4,5‐dihydro‐1 H ‐pyrazole‐1‐carbothioamide Derivatives
Author(s) -
Şentürk Kerem,
Tan Oya Unsal,
Çiftçi Samiye Yabanoğlu,
Uçar Gülberk,
Palaska Erhan
Publication year - 2012
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201100448
Subject(s) - chemistry , monoamine oxidase , pyrazole , in vitro , selectivity , stereochemistry , aryl , gene isoform , monoamine oxidase b , medicinal chemistry , enzyme , biochemistry , organic chemistry , alkyl , catalysis , gene
Sixteen 3‐aryl‐5‐(4‐fluorophenyl)‐ N ‐substituted‐4,5‐dihydro‐1 H ‐pyrazole‐1‐carbothioamide derivatives were synthesized and their structure were identified by UV, IR, 1 H 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‐1 H ‐pyrazole‐1‐carbothioamide (1.0 × 10 −3 µM) 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‐1 H ‐pyrazole‐1‐carbothioamide to hMAO‐A was also predicted using docking studies.