7-chloro-N-[[4-(4-chlorophenyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine | 1404112-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-chloro-N-[[4-(4-chlorophenyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine
• 英文别名: 7-chloro-N-[[5-(4-chlorophenyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine
• CAS: 1404112-75-9
• 化学式: C₁₉H₁₄Cl₂N₄
• 分子量: 369.253
• InChiKey: JPMKTHCRXXPJCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 聚合甲醛 、 7-chloro-N-[[4-(4-chlorophenyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以60%的产率得到7-chloro-N-[[4-(4-chlorophenyl)-5-(pyrrolidin-1-ylmethyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline

  摘要：

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.040
• 作为产物：
  描述：

  tert-butoxycarbonyl (4-(4-chlorophenyl)-1H-imidazol-2-yl)methylamine 在 三氟乙酸 、 苯酚 作用下， 反应 3.5h， 生成 7-chloro-N-[[4-(4-chlorophenyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline

  摘要：

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.040

文献信息

• Synthesis and antiplasmodial activity of new heteroaryl derivatives of 7-chloro-4-aminoquinoline
  作者：Manolo Casagrande、Anna Barteselli、Nicoletta Basilico、Silvia Parapini、Donatella Taramelli、Anna Sparatore

  DOI：10.1016/j.bmc.2012.07.040

  日期：2012.10

  With the aim to investigate the effect of different heterocyclic rings linked to the 4-aminoquinoline nucleus on the antimalarial activity, a set of 7-chloro-N-(heteroaryl)-methyl-4-aminoquinoline and 7-chloro-N-(heteroaryl)-4-aminoquinoline was synthesized and tested in vitro against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited from moderate to high antiplasmodial activities. The activity was strongly influenced both by the presence of a methylenic group, as a spacer between the 4-aminoquinoline and the heterocyclic ring, and by the presence of a basic head. The most potent molecules inhibited the growth of both CQ-S and CQ-R strains of P. falciparum with IC50 < 30 nM and were not toxic against human endothelial cells. These results confirm that the presence of an heteroaryl moiety in the side chain of 7-chloro-4-aminoquinoline is useful for the design and development of new powerful antimalarial agents. (C) 2012 Elsevier Ltd. All rights reserved.