(E)-1-(2-chlorobenzyl)-5-((4-hydroxy-3-methoxybenzylidene)amino)-1H-imidazole-4-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-1-(2-chlorobenzyl)-5-((4-hydroxy-3-methoxybenzylidene)amino)-1H-imidazole-4-carbonitrile
• 英文别名: 1-[(2-chlorophenyl)methyl]-5-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]imidazole-4-carbonitrile
• 化学式: C₁₉H₁₅ClN₄O₂
• 分子量: 366.807
• InChiKey: ZTYQPSJUCLDIJP-LSHDLFTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2-chlorobenzyl)-(Z)-N-[2-amino-1,2-dicyanovinyl]formamidine 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.42h， 生成 (E)-1-(2-chlorobenzyl)-5-((4-hydroxy-3-methoxybenzylidene)amino)-1H-imidazole-4-carbonitrile
  参考文献：
  名称：

  Imine/amide–imidazole conjugates derived from 5-amino-4-cyano- N 1-substituted benzyl imidazole: Microwave-assisted synthesis and anticancer activity via selective topoisomerase-II-α inhibition

  摘要：

  Microwave-accelerated synthesis and anticancer activity of novel imine/ amide-imidazole conjugates derived from 5-amino-4-cyano-N1-substituted benzyl imidazole against a panel of seven cancer cell lines are reported for the first time. Compounds ARK-4, 10 and 12 in the series show promising in vitro anti proliferative activity with low micromolar IC50 values against A-459 (lung), Hep-G2 (liver) and H-460 (liver) cancer cell lines. Compounds caused the increase in ROS levels as well as mitochondrial membrane depolarization, which might induce apoptosis. Further, mechanistic interventions on biological and molecular modeling data supported that compounds inhibited topoisomerase-II selectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.020

文献信息

• Imine/amide–imidazole conjugates derived from 5-amino-4-cyano- N 1-substituted benzyl imidazole: Microwave-assisted synthesis and anticancer activity via selective topoisomerase-II-α inhibition
  作者：Arvind Negi、Jimi Marin Alex、Suyog M. Amrutkar、Ashish T. Baviskar、Gaurav Joshi、Sandeep Singh、Uttam C. Banerjee、Raj Kumar

  DOI：10.1016/j.bmc.2015.07.020

  日期：2015.9

  Microwave-accelerated synthesis and anticancer activity of novel imine/ amide-imidazole conjugates derived from 5-amino-4-cyano-N1-substituted benzyl imidazole against a panel of seven cancer cell lines are reported for the first time. Compounds ARK-4, 10 and 12 in the series show promising in vitro anti proliferative activity with low micromolar IC50 values against A-459 (lung), Hep-G2 (liver) and H-460 (liver) cancer cell lines. Compounds caused the increase in ROS levels as well as mitochondrial membrane depolarization, which might induce apoptosis. Further, mechanistic interventions on biological and molecular modeling data supported that compounds inhibited topoisomerase-II selectively. (C) 2015 Elsevier Ltd. All rights reserved.