Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives


Özdemir Z., Kandilci H. B., Gümüşel B., Çaliş Ü., Bilgin A. A.

European Journal of Medicinal Chemistry, vol.42, no.3, pp.373-379, 2007 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 42 Issue: 3
  • Publication Date: 2007
  • Doi Number: 10.1016/j.ejmech.2006.09.006
  • Journal Name: European Journal of Medicinal Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.373-379
  • Keywords: pyrazolines, thiocarbamoyl compounds, antidepressant activity, anticonvulsant activity, MONOAMINE-OXIDASE, 1,3,5-TRISUBSTITUTED PYRAZOLINES
  • Lokman Hekim University Affiliated: No

Abstract

Twelve 1-phenyl-, 1-thiocarbamoyl- and 1-N-substituted thiocarbamoyl-3-(2-furyl)-5-phenyl/(2-furyl)-2-pyrazoline derivatives were synthesized. The chemical structures of the compounds were proved by IR, 1H NMR, Mass spectrometric data and microanalyses. The antidepressant activities of the compounds were investigated by Porsolt's behavioural despair (forced swimming) test on albino mice. 1-N-Ethylthiocarbamoyl-3-(2-furyl)-5-phenyl-2-pyrazoline (6) and 1-N-allylthiocarbamoyl-3,5-di(2-furyl)-2-pyrazoline (11) reduced 33.80-31.42% duration of immobility times at 10 mg kg-1 dose level. Anticonvulsant activities of the compounds were determined by maximal electroshock seizure (MES) and subcutaneous pentylenetetrazole (metrazol) (scMet.) tests, neurotoxicities were determined by rotarod toxicity test on albino mice. 1,5-Diphenyl-3-(2-furyl)-2-pyrazoline (2), 1-N-allylthiocarbamoyl-3-(2-furyl)-5-phenyl-2-pyrazoline (7), 1-N-allylthiocarbamoyl-3,5-di(2-furyl)-2-pyrazoline (11) and 1-N-phenylthiocarbamoyl-3,5-di(2-furyl)-2-pyrazoline (12) were active at 100-300 mg kg-1 dose levels. 1-Thiocarbamoyl-3,5-di(2-furyl)-2-pyrazoline (4), 1-N-methylthiocarbamoyl-3,5-di(2-furyl)-2-pyrazoline (9) and 1-N-ethylthiocarbamoyl-3,5-di(2-furyl)-2-pyrazoline (10) were found protective against MES and scMet. at 30-300 mg kg-1 dose levels. © 2006 Elsevier Masson SAS. All rights reserved.