2-[(3-chloro-10H-indolo[3,2-b]quinolin-11-yl)oxy]-N,N-diethylethanamine | 1254031-87-2

• 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: 2-[(3-chloro-10H-indolo[3,2-b]quinolin-11-yl)oxy]-N,N-diethylethanamine
• CAS: 1254031-87-2
• 化学式: C₂₁H₂₂ClN₃O
• 分子量: 367.878
• InChiKey: GYPSVEWXFPTGRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-chloro-5H,10H,11H-indolo[3,2-b]quinolin-11-one 、 2-二乙氨基氯乙烷盐酸盐 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 以21%的产率得到3-chloro-5,10-bis[2-(diethylamino)ethyl]-5H-indolo[3,2-b]quinolin-11(10H)-one
  参考文献：
  名称：

  Bis-alkylamine quindolone derivatives as new antimalarial leads

  摘要：

  Quindolone derivatives, designed to target the malaria parasite digestive vacuole and heme detoxification pathway, have been synthesized by reaction with 2-chloro-N,N-diethylethanamine. This reaction gave N,O-, N,N- and O-alkylated products containing one or two basic side-chains. The compounds were evaluated for antiplasmodial activity against the chloroquine-resistant Plasmodium falciparum W2 strain and for cytotoxicity in HepG2 A16 hepatic cells. By incorporating alkylamine side chains and chlorine atoms in the quindolone nucleus we transformed the inactive tetracyclic parent quindolones into moderate or highly active and selective antimalarial compounds. The most active and selective compound, 5c, showed an IC50 = 51 nM for P. falciparum and a selectivity ratio of 98. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.043

文献信息

• Bis-alkylamine quindolone derivatives as new antimalarial leads
  作者：João Lavrado、Kaamil Gani、Pedro A. Nobre、Sofia A. Santos、Paula Figueiredo、Dinora Lopes、Virgílio do Rosário、Jiri Gut、Philip J. Rosenthal、Rui Moreira、Alexandra Paulo

  DOI：10.1016/j.bmcl.2010.08.043

  日期：2010.10

  Quindolone derivatives, designed to target the malaria parasite digestive vacuole and heme detoxification pathway, have been synthesized by reaction with 2-chloro-N,N-diethylethanamine. This reaction gave N,O-, N,N- and O-alkylated products containing one or two basic side-chains. The compounds were evaluated for antiplasmodial activity against the chloroquine-resistant Plasmodium falciparum W2 strain and for cytotoxicity in HepG2 A16 hepatic cells. By incorporating alkylamine side chains and chlorine atoms in the quindolone nucleus we transformed the inactive tetracyclic parent quindolones into moderate or highly active and selective antimalarial compounds. The most active and selective compound, 5c, showed an IC50 = 51 nM for P. falciparum and a selectivity ratio of 98. (C) 2010 Elsevier Ltd. All rights reserved.