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

• Published in: European journal of medicinal chemistry Vol. 42; no. 3; pp. 373 - 379
• Main Authors: Özdemir, Zuhal, Kandilci, H. Burak, Gümüşel, Bülent, Çalış, Ünsal, Bilgin, A. Altan
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Masson SAS 01-03-2007; Elsevier
• Subjects: Animals; Anticonvulsant activity; Anticonvulsants - chemical synthesis; Anticonvulsants - pharmacology; Anticonvulsants - toxicity; Anticonvulsants. Antiepileptics. Antiparkinson agents; Antidepressant activity; Antidepressive Agents - chemical synthesis; Antidepressive Agents - pharmacology; Antidepressive Agents - toxicity; Biological and medical sciences; Convulsants; Electroshock; Furans - chemical synthesis; Furans - pharmacology; Magnetic Resonance Spectroscopy; Male; Medical sciences; Mice; Neuropharmacology; Neurotoxicity Syndromes - psychology; Pentylenetetrazole; Pharmacology. Drug treatments; Postural Balance - drug effects; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease); Psychology. Psychoanalysis. Psychiatry; Psychopharmacology; Pyrazoles - chemical synthesis; Pyrazoles - pharmacology; Pyrazolines; Seizures - chemically induced; Seizures - drug therapy; Spectrophotometry, Ultraviolet; Structure-Activity Relationship; Swimming - psychology; Thiocarbamoyl compounds; Thiocarbamoyl compounds; Anticonvulsant activity; Antidepressant activity; Pyrazolines; Psychotropic; Toxicity; Rodentia; Furan derivatives; Nervous system; Anticonvulsant; Biological activity; Vertebrata; Neurotoxicity; Mammalia; Mouse; Animal; Pyrazole derivatives; Antidepressant agent; Chemical synthesis
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2006.09.006

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.
[Display omitted] Several 3-(2-furyl)-2-pyrazoline derivatives were synthesized and evaluated for their antidepressant and anticonvulsant activities. Our pharmacological results indicate that they seem to be really promising compounds for their anticonvulsant activities.