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

Eur J Med Chem. 2007 Mar;42(3):373-9. doi: 10.1016/j.ejmech.2006.09.006. Epub 2006 Oct 25.

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, (1)H 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anticonvulsants / chemical synthesis*
  • Anticonvulsants / pharmacology*
  • Anticonvulsants / toxicity
  • Antidepressive Agents / chemical synthesis*
  • Antidepressive Agents / pharmacology*
  • Antidepressive Agents / toxicity
  • Convulsants
  • Electroshock
  • Furans / chemical synthesis*
  • Furans / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Neurotoxicity Syndromes / psychology
  • Pentylenetetrazole
  • Postural Balance / drug effects
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology*
  • Seizures / chemically induced
  • Seizures / drug therapy
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship
  • Swimming / psychology

Substances

  • Anticonvulsants
  • Antidepressive Agents
  • Convulsants
  • Furans
  • Pyrazoles
  • Pentylenetetrazole