Palaska E, Aytemir M, Uzbay I T, Erol D
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100, Ankara, Turkey.
Eur J Med Chem. 2001 Jun;36(6):539-43. 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 mgkg(-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.
通过使1,3 - 二苯基 - 2 - 丙烯 - 1 - 酮与水合肼反应合成了10种新的3,5 - 二苯基 - 2 - 吡唑啉衍生物。通过红外光谱、1H - NMR光谱数据和微量分析证实了这些化合物的化学结构。通过对瑞士 - 韦伯斯特小鼠进行“波索尔特行为绝望试验”评估了这些化合物的抗抑郁活性。3 - (4 - 甲氧基苯基) - 5 - (3,4 - 二甲氧基苯基) - 2 - 吡唑啉、3 - (4 - 甲氧基苯基) - 5 - (2 - 氯 - 3,4 - 二甲氧基苯基) - 2 - 吡唑啉和3 - (4 - 氯苯基) - 5 - (2 - 氯 - 3,4 - 二甲氧基苯基) - 2 - 吡唑啉在100 mgkg(-1)剂量水平下使不动时间减少了41.94 - 48.62%。此外，还发现吡唑啉环3位苯环上的4 - 甲氧基和4 - 氯取代基增加了抗抑郁活性；在小鼠中用溴和甲基取代基取代这些基团会降低活性。
