Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines

• Published in: European journal of medicinal chemistry Vol. 36; no. 6; pp. 539 - 543
• Main Authors: Palaska, Erhan, Aytemir, Mutlu, Uzbay, İ.Tayfun, Erol, Dilek
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Masson SAS 01-06-2001; Elsevier
• Subjects: 3,5-diphenyl-2-pyrazolines; Animals; antidepressant activity; Antidepressive Agents - chemical synthesis; Antidepressive Agents - pharmacology; Biological and medical sciences; Clomipramine - chemical synthesis; Clomipramine - chemistry; Clomipramine - pharmacology; Dose-Response Relationship, Drug; Drug Design; Drug Evaluation, Preclinical; Forced-Swimming Test; Magnetic Resonance Spectroscopy; Male; Medical sciences; Mice; Neuropharmacology; Neuropsychological Tests; Pharmacology. Drug treatments; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease); Psychology. Psychoanalysis. Psychiatry; Psychopharmacology; Pyrazoles - chemical synthesis; Pyrazoles - chemistry; Pyrazoles - pharmacology; Spectrophotometry, Infrared; Structure-Activity Relationship; Swimming; Tranylcypromine - chemical synthesis; Tranylcypromine - chemistry; Tranylcypromine - pharmacology; 3,5-diphenyl-2-pyrazolines; Forced-Swimming Test; antidepressant activity; Five membered ring; Intraperitoneal administration; Nitrogen heterocycle; Psychotropic; Rodentia; Benzene derivatives; Behavioral despair; Vertebrata; Mammalia; Structure activity relation; Mouse; Chlorine Organic compounds; Animal; Antidepressant agent; Behavior; Chemical synthesis
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/S0223-5234(01)01243-0

Ten new 3,5-diphenyl-2-pyrazoline derivatives were synthesised by reacting 1,3-diphenyl-2-propen-1-one with hydrazine hydrate. The chemical structures of the compounds were proved by means of their IR,
1H-NMR spectroscopic data and microanalyses. The antidepressant activities of these compounds were evaluated by the ‘Porsolt Behavioural Despair Test’ on Swiss–Webster mice. 3-(4-Methoxyphenyl)-5-(3,4-dimethoxyphenyl)-2-pyrazoline, 3-(4-methoxyphenyl)-5-(2-chloro-3,4-dimethoxyphenyl)-2-pyrazoline and 3-(4-chlorophenyl)-5-(2-chloro-3,4-dimethoxyphenyl)-2-pyrazoline reduced 41.94–48.62% immobility times at 100 mg
kg
−1 dose level. In addition, it was found that 4-methoxy and 4-chloro substituents on the phenyl ring at position 3 of the pyrazoline ring increased the antidepressant activity; the replacement of these groups by bromo and methyl substituents decreased activity in mice.