3-(2-chloro-3,4-dimethoxyphenyl)-1-(4-chlorophenyl)prop-2-en-1-one | 399031-85-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-chloro-3,4-dimethoxyphenyl)-1-(4-chlorophenyl)prop-2-en-1-one
• CAS: 399031-85-7
• 化学式: C₁₇H₁₄Cl₂O₃
• 分子量: 337.202
• InChiKey: WSNWGBITHKFPKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(2-chloro-3,4-dimethoxyphenyl)-1-(4-chlorophenyl)prop-2-en-1-one 在 二氮烯 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以94.3%的产率得到5-(2-chloro-3,4-dimethoxyphenyl)-3-(4-chlorophenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

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

  摘要：

  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, H-1-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. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01243-0
• 作为产物：
  描述：

  2-氯-3,4-二甲氧基苯甲醛 、 对氯苯乙酮 生成 3-(2-chloro-3,4-dimethoxyphenyl)-1-(4-chlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  1-硫代氨基甲酰基-3,5-二苯基-4,5-二氢-1H-吡唑衍生物的合成及单胺氧化酶抑制活性

  摘要：

  十新1-硫代氨基甲酰基-3-(苯基和/或4-取代苯基)-5-(3,4-二甲氧基苯基和/或2-氯-3,4-二甲氧基苯基)-4,5-二氢-1H-吡唑衍生物是通过 1,3-diphenylpropen-1-ones 和氨基硫脲反应合成的。通过IR、1H-NMR、ESI-MS光谱数据和元素分析验证了化合物的化学结构。通过体外试验研究了所有化合物选择性抑制单胺氧化酶 (MAO) 的能力。从大鼠肝脏匀浆和人血小板的线粒体提取物中分离和纯化单胺氧化酶。将化合物的单胺氧化酶抑制活性与帕吉林和氯吉林进行比较。大多数化合物抑制大鼠肝脏匀浆的总活性。1-硫代氨基甲酰基-3-(4-甲氧基苯基)-5-(3,4-二甲氧基苯基)-4,5-二氢-1H-吡唑和1-硫代氨基甲酰基-3-(4-甲氧基苯基)对单胺氧化酶-A的抑制作用) -5- (2-氯-3,4-二甲氧基苯基) -4,5-二氢-1H-吡唑被检测到与氯吉林一样有效。合成化合物对大鼠肝脏单胺氧化酶-A

  DOI：

  10.1002/ardp.200700159

文献信息

• Synthesis and antidepressant activities of some 1,3,5-triphenyl-2-pyrazolines
  作者：E Palaska、D Erol、R Demirdamar

  DOI：10.1016/s0223-5234(96)80005-5

  日期：1996.1

  Ten new 1,3,5-triphenyl-2-pyrazoline derivatives were synthesized by reacting 1,3-diphenyl-2-propen-1-one with phenylhydrazine. The chemical structures of the compounds were proved by means of their UV, IR, H-1-NMR spectroscopic data and elementary analyses. The antidepressant activities of these compounds were screened by the Porsolt behavioral despair test. 1-Phenyl-3-(4-methylphenyl)-5-(3,4-dimethoxyphenyl)-2-pyrazoline and 1-phenyl-3-(4-methylphenyl)-5-(2-chloro-3,4-dimethoxyphenyl)-2-prazoline showed significant antidepressant activity compared with clomipramine and tranylcypromine. A methyl substituent on the phenyl ring at position 3 of the pyrazoline ring enhances the antidepressant activity; the replacement of this methyl group by chloro or bromo substituents decreases the activity. In addition, introduction of a chloro substituent to the phenyl at the position 5 decreases the antidepressant activity.