7-chloro-N-[[5-(pyrrolidin-1-ylmethyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine | 1404112-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-chloro-N-[[5-(pyrrolidin-1-ylmethyl)-1H-imidazol-2-yl]methyl]quinolin-4-amine
• CAS: 1404112-72-6
• 化学式: C₁₈H₂₀ClN₅
• 分子量: 341.843
• InChiKey: LQIIESHCEKKFNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,7-二氯喹啉 在 溶剂黄146 、 N,N-二异丙基乙胺 、 苯酚 作用下， 以 水 为溶剂， 反应 25.0h， 生成 7-chloro-N-[[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

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.