8-chloro-5-methyl-5H-indolo[3,2-c]quinoline | 1140885-97-7

• 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: 8-chloro-5-methyl-5H-indolo[3,2-c]quinoline
• 英文别名: 8-chloroisocryptolepine；CMIQ；8-Chloro-5-methyl-indolo[3,2-c]quinoline；8-chloro-5-methylindolo[3,2-c]quinoline
• CAS: 1140885-97-7
• 化学式: C₁₆H₁₁ClN₂
• 分子量: 266.73
• InChiKey: JUNADHPIVBCNEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯喹啉 在 N-氯代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 44.5h， 生成 8-chloro-5-methyl-5H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  Synthesis and antimalarial evaluation of novel isocryptolepine derivatives

  摘要：

  A series of mono- and di-substituted analogues of isocryptolepine have been synthesized and evaluated for in vitro antimalarial activity against chloroquine sensitive (3D7) and resistant (W2mef) Plasmodium falciparum and for cytotoxicity (3T3 cells). Di-halogenated compounds were the most potent derivatives and 8-bromo-2-chloroisocryptolepine displayed the highest selectivity index (106; the ratio of cytotoxicity (IC(50) = 9005 nM) to antimalarial activity (IC(50) = 85 nM)). Our evaluation of novel isocryptolepine compounds has demonstrated that di-halogenated derivatives are promising antimalarial lead compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.037

文献信息

• A Facile and Expeditious Synthesis of Cryptosanguinolentines
  作者：Dalip Kumar、Maruthi Kumar. N.、V. S. Rao

  DOI：10.1246/cl.2009.156

  日期：2009.2.5

  A simple and efficient synthesis of naturally occurring cryptosanguinolentines is described. Neat reaction of easily accessible 1-methyl-1,2,3,4-tetrahydroquinolin-4-ones and aryl hydrazines in the presence of p-toluenesulfonic acid at 100 °C rapidly afforded cryptosanguinolentines in very good yields.

  本文描述了天然存在的隐血素类化合物的一种简单有效的合成方法。在100°C下，在四甲基苯磺酸存在下，易得的1-甲基-1,2,3,4-四氢喹啉-4-酮和芳基肼的简单反应迅速产生了隐血素类化合物，且收率很高。
• Regiodivergent Synthesis of 11 <i>H</i> ‐Indolo[3,2‐ <i>c</i> ]quinolines and Neocryptolepine from a Common Starting Material
  作者：Katja S. Håheim、Bjarte Aarmo Lund、Magne O. Sydnes

  DOI：10.1002/ejoc.202300137

  日期：——

  A common intermediate gives easy access to both neocryptolepine and isocryptolepine analogues in up to 80 % and 95 % yield, respectively.

  一种常见的中间体可以很容易地以高达 80% 和 95% 的收率分别获得新隐藤碱和异隐藤碱类似物。
• Synthesis and antimalarial evaluation of novel isocryptolepine derivatives
  作者：Louise R. Whittell、Kevin T. Batty、Rina P.M. Wong、Erin M. Bolitho、Simon A. Fox、Timothy M.E. Davis、Paul E. Murray

  DOI：10.1016/j.bmc.2011.10.037

  日期：2011.12

  A series of mono- and di-substituted analogues of isocryptolepine have been synthesized and evaluated for in vitro antimalarial activity against chloroquine sensitive (3D7) and resistant (W2mef) Plasmodium falciparum and for cytotoxicity (3T3 cells). Di-halogenated compounds were the most potent derivatives and 8-bromo-2-chloroisocryptolepine displayed the highest selectivity index (106; the ratio of cytotoxicity (IC(50) = 9005 nM) to antimalarial activity (IC(50) = 85 nM)). Our evaluation of novel isocryptolepine compounds has demonstrated that di-halogenated derivatives are promising antimalarial lead compounds. (C) 2011 Elsevier Ltd. All rights reserved.