ethyl 1-[3-((7-chloroquinolin-4-yl)amino)propyl]-2-methyl-5-(4-chlorophenyl)-1H-pyrrole-3-carboxylate | 1251469-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-[3-((7-chloroquinolin-4-yl)amino)propyl]-2-methyl-5-(4-chlorophenyl)-1H-pyrrole-3-carboxylate
• CAS: 1251469-34-7
• 化学式: C₂₆H₂₅Cl₂N₃O₂
• 分子量: 482.409
• InChiKey: VIIRGBVKURBVGE-UHFFFAOYSA-N

物化性质

• 熔点：
  148.5-151.5 °C(Solvent: Dichloromethane; Diethyl ether)
• 沸点：
  653.6±55.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  56.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  四氢吡咯 、 ethyl 1-[3-((7-chloroquinolin-4-yl)amino)propyl]-2-methyl-5-(4-chlorophenyl)-1H-pyrrole-3-carboxylate 在 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 0.58h， 以78%的产率得到[5-(4-chlorophenyl)-1-(3-((7-chloroquinolin-4-yl)amino)-propyl)-2-methyl-1H-pyrrol-3-yl](pyrrolidin-1-yl)methane
  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：

  N-(7-chloroquinolin-4-yl)propane-1,3-diamine 、 2-乙酰基-4-(4-氯苯基)-4-氧代丁酸乙酯 在 溶剂黄146 、 sodium hydroxide 作用下， 反应 2.0h， 以75%的产率得到ethyl 1-[3-((7-chloroquinolin-4-yl)amino)propyl]-2-methyl-5-(4-chlorophenyl)-1H-pyrrole-3-carboxylate
  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