1-((7-chloroquinolin-4-yl)amino)-2-methyl-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylic acid | 1251469-43-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-((7-chloroquinolin-4-yl)amino)-2-methyl-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylic acid
• CAS: 1251469-43-8
• 化学式: C₂₁H₁₅ClN₄O₄
• 分子量: 422.827
• InChiKey: PDZACXATLZLNNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  110.29
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-((7-chloroquinolin-4-yl)amino)-2-methyl-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylic acid 、 二乙胺 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以74%的产率得到1-((7-chloroquinolin-4-yl)amino)-2-methyl-5-(4-nitrophenyl)-1H-pyrrole-3-(N,N-diethyl)-carboxamide
  参考文献：
  名称：

  Synthesis, antimalarial activity, and cellular toxicity of new arylpyrrolylaminoquinolines

  摘要：

  A set of nine new arylpyrrolyl derivatives of 7-chloro-4-aminoquinoline, characterized by different substituents on the phenyl ring or different distance between the pyrrolic nitrogen and the 4-aminoquinoline, has been synthesized and tested for their activity against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited activity against the CQ-S strain in the low nM range, comparable to that of chloroquine. Some of them were also highly active against the CQ-R strain and not toxic against normal cells. The antimalarial activity of this new class of compounds seems to be related to the inhibition of heme detoxification process of parasites, as in the case of chloroquine. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.001
• 作为产物：
  描述：

  ethyl 1-[(7-chloroquinolin-4-yl)amino]-2-methyl-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylate 在 lithium hydroxide monohydrate 、 水 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以96%的产率得到1-((7-chloroquinolin-4-yl)amino)-2-methyl-5-(4-nitrophenyl)-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, antimalarial activity, and cellular toxicity of new arylpyrrolylaminoquinolines

  摘要：

  A set of nine new arylpyrrolyl derivatives of 7-chloro-4-aminoquinoline, characterized by different substituents on the phenyl ring or different distance between the pyrrolic nitrogen and the 4-aminoquinoline, has been synthesized and tested for their activity against D-10 (CQ-S) and W-2 (CQ-R) strains of Plasmodium falciparum. All compounds exhibited activity against the CQ-S strain in the low nM range, comparable to that of chloroquine. Some of them were also highly active against the CQ-R strain and not toxic against normal cells. The antimalarial activity of this new class of compounds seems to be related to the inhibition of heme detoxification process of parasites, as in the case of chloroquine. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.001