(E)-4-chloro-N'-(4-(dimethylamino)benzylidene)benzohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-chloro-N'-(4-(dimethylamino)benzylidene)benzohydrazide
• 英文别名: 4-chloro-N'-[4-(dimethylamino)benzylidene]benzohydrazide；4-chloro-N-[(E)-[4-(dimethylamino)phenyl]methylideneamino]benzamide
• 化学式: C₁₆H₁₆ClN₃O
• 分子量: 301.776
• InChiKey: WGXXBEBMZAVWKW-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰肼 、 对二甲氨基苯甲醛 以 乙醇 为溶剂， 以54%的产率得到(E)-4-chloro-N'-(4-(dimethylamino)benzylidene)benzohydrazide
  参考文献：
  名称：

  (Hetero-)(arylidene)arylhydrazides as Multitarget-Directed Monoamine Oxidase Inhibitors

  摘要：

  Fourteen (hetero-)(arylidene)arylhydrazide derivatives (ABH1-ABH14) were synthesized, and their inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE) were evaluated. Compound ABHS most potently inhibited MAO-B with an IC50 value of 0.025 +/- 0.0019 mu M; ABH2 and ABH3 exhibited high IC so values as well. Most of the compounds weakly inhibited MAO-A, except ABHS (IC50 = 3.31 +/- 0.41 mu M). Among the active compounds, ABH2 showed the highest selectivity index (SI) of 174 for MAO-B, followed by ABHS (SI = 132). ABH3 and ABHS effectively inhibited AChE with IC so values of 15.7 +/- 6.52 and 16.5 +/- 7.29 mu M, respectively, whereas the other compounds were weak inhibitors of AChE. ABHS was shown to be a reversible competitive inhibitor for MAO-A and MAO-B with K-i values of 0.96 +/- 0.19 and 0.024 +/- 0.0077 mu M, respectively, suggesting that this molecule can be considered as an interesting candidate for further development as a multitarget inhibitor relating to neurodegenerative disorders.

  DOI：

  10.1021/acscombsci.0c00136

文献信息

• (Hetero-)(arylidene)arylhydrazides as Multitarget-Directed Monoamine Oxidase Inhibitors
  作者：Ashique Palakkathondi、Jong Min Oh、Sanal Dev、T. M. Rangarajan、Swafvan Kaipakasseri、Fathima Sahla Kavully、Nicola Gambacorta、Orazio Nicolotti、Hoon Kim、Bijo Mathew

  DOI：10.1021/acscombsci.0c00136

  日期：2020.11.9

  Fourteen (hetero-)(arylidene)arylhydrazide derivatives (ABH1-ABH14) were synthesized, and their inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE) were evaluated. Compound ABHS most potently inhibited MAO-B with an IC50 value of 0.025 +/- 0.0019 mu M; ABH2 and ABH3 exhibited high IC so values as well. Most of the compounds weakly inhibited MAO-A, except ABHS (IC50 = 3.31 +/- 0.41 mu M). Among the active compounds, ABH2 showed the highest selectivity index (SI) of 174 for MAO-B, followed by ABHS (SI = 132). ABH3 and ABHS effectively inhibited AChE with IC so values of 15.7 +/- 6.52 and 16.5 +/- 7.29 mu M, respectively, whereas the other compounds were weak inhibitors of AChE. ABHS was shown to be a reversible competitive inhibitor for MAO-A and MAO-B with K-i values of 0.96 +/- 0.19 and 0.024 +/- 0.0077 mu M, respectively, suggesting that this molecule can be considered as an interesting candidate for further development as a multitarget inhibitor relating to neurodegenerative disorders.