2-{4-(2-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)piperazin-1-yl}ethanol | 1150313-41-9

• 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-{4-(2-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)piperazin-1-yl}ethanol
• 英文别名: 2-[4-(2-Chloro-5-methylindolo[2,3-b]quinolin-11-yl)piperazin-1-yl]ethanol
• CAS: 1150313-41-9
• 化学式: C₂₂H₂₃ClN₄O
• 分子量: 394.904
• InChiKey: BCSRSEZIIMZZRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-羟乙基哌嗪 、 2,11-dichloro-5-methyl-5H-indolo[2,3-b]quinoline 以76%的产率得到2-{4-(2-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)piperazin-1-yl}ethanol
  参考文献：
  名称：

  Synthesis and Antiplasmodial Activity of Aminoalkylamino-Substituted Neocryptolepine Derivatives

  摘要：

  A series of chloro- and aminoalkylamino-substituted neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives were synthesized and evaluated as antiplasmodial agents. The evaluation also included cytotoxicity (MRCS cells), inhibition of beta-hematin formation, and DNA interactions (DNA-methyl green assay). Introduction of aminoalkylamino chains increased the antiplasmodial activity of the neocryptolepine core substantially. The most efficient compounds showed antiplasmodial activities in the nanomolar range. N-1,N-1-Diethyl-N-4-(5-methyl-5H-indolo[2,3-b]quinolin-8-yl)pentane-1,4-diamine 11c showed an IC50 of 0.01 mu M and a selectivity index of 1800.

  DOI：

  10.1021/jm801490z

文献信息

• Synthesis and Antiplasmodial Activity of Aminoalkylamino-Substituted Neocryptolepine Derivatives
  作者：Ibrahim El Sayed、Pieter Van der Veken、Koen Steert、Liene Dhooghe、Steven Hostyn、Gitte Van Baelen、Guy Lemière、Bert U. W. Maes、Paul Cos、Louis Maes、Jurgen Joossens、Achiel Haemers、Luc Pieters、Koen Augustyns

  DOI：10.1021/jm801490z

  日期：2009.5.14

  A series of chloro- and aminoalkylamino-substituted neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives were synthesized and evaluated as antiplasmodial agents. The evaluation also included cytotoxicity (MRCS cells), inhibition of beta-hematin formation, and DNA interactions (DNA-methyl green assay). Introduction of aminoalkylamino chains increased the antiplasmodial activity of the neocryptolepine core substantially. The most efficient compounds showed antiplasmodial activities in the nanomolar range. N-1,N-1-Diethyl-N-4-(5-methyl-5H-indolo[2,3-b]quinolin-8-yl)pentane-1,4-diamine 11c showed an IC50 of 0.01 mu M and a selectivity index of 1800.