3-chloro-11H-indolo[3,2-c]quinoline | 116792-07-5

• 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: 3-chloro-11H-indolo[3,2-c]quinoline
• CAS: 116792-07-5
• 化学式: C₁₅H₉ClN₂
• 分子量: 252.703
• InChiKey: ROOSRIFSHAIYNI-UHFFFAOYSA-N

物化性质

• 沸点：
  500.2±30.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-chloro-11H-indolo[3,2-c]quinoline 以60%的产率得到
  参考文献：
  名称：

  Werbel L. M., Kesten S. J., Turner W. R., Eur. J. Med. Chem, 28 (1993) N 11, S 837-852

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-氯苯基)-1H-吲哚-3-甲醛 在 吡啶 、 盐酸羟胺 、 四氯化锡 、 三乙胺 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 3-chloro-11H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  SnCl4催化吲哚-3-甲醛肟环化合成11H-吲哚[3,2-c]喹啉

  摘要：

  开发了一种通过 SnCl4 催化 2-芳基吲哚-3-甲醛 O-乙酰肟分子内亲电胺化合成 11H-吲哚并[3,2-c] 喹啉的新方法。

  DOI：

  10.1007/s11172-019-2697-7

文献信息

• Palladium-catalyzed regioselective aerobic oxidative cyclization via C–H activation in chloroquine analogues: synthesis and cytotoxic study
  作者：Gopal Senthil Kumar、Mohamed Ashraf Ali、Tan Soo Choon、Karnam Jayarampillai Rajendra Prasad

  DOI：10.1007/s00706-015-1474-z

  日期：2015.12

  The intramolecular regioselective aerobic oxidative cyclization via two types of discrete C-H activation in 7-chloroquinoline analogues is described. All the synthesized compounds are screened against three human cancer cell lines (CCRF-CEM, HT29, and MCF7) for their anticancer activities. Among them, chloroquine analogues with naphthalene ring either substituted/fused form enhance remarkable cytotoxic activity against human breast adenocarcinoma cancer cell line (MCF-7) which outranged positive control doxorubicin. Similarly, 3-chloro-7H,12H-pyrazolo[5,4-b]quinolino[3,2-c]indole has possessed significant activity against all the tested cell lines and outranged activity against CCRF-CEM cell line.
• Structure-activity relationships of antimalarial indolo[3,2-c]quinolines [1, 2]
  作者：LM Werbel、SJ Kesten、WR Turner

  DOI：10.1016/0223-5234(93)90036-e

  日期：1993.1

  Structure-activity relationships have been ascertained and chemical methodology developed for a series of antimalarial 3-chloroindolo[3,2-c]quinoline-5-oxides. The basic side chain as well as the ring N-oxide are critical for antimalarial activity as is a bromine or chlorine in position 3. Substitution at positions 7, 8, 9, 10 is not essential, although the most potent analog in our studies was the 8-nitro compound 4vv.
• 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.
• Iodine catalyzed one-pot synthesis of chloro-substituted linear and angular indoloquinolines and in vitro antiproliferative activity study of different indoloquinolines
  作者：Prakash T. Parvatkar、Amrendra Kumar Ajay、Manoj Kumar Bhat、Perunninakulath S. Parameswaran、Santosh G. Tilve

  DOI：10.1007/s00044-012-0015-0

  日期：2013.1

  This article describes a facile one-pot synthesis of different chloro-substituted linear and angular indoloquinolines using iodine as a catalyst and in vitro antiproliferative activity of these chloro-substituted indoloquinolines (3e and 3f) and some indolo[2,3-b]quinolines (3a-d) against human hepatocellular carcinoma HepG2 and human breast carcinoma MCF-7 cells. Anti-proliferative assay against human hepatocellular carcinoma HepG2 and human breast carcinoma MCF-7 cells indicated methyl-substituted 6H-indolo[2,3-b]quinoline 3c to be the most active and the parent 6H-indolo[2,3-b]quinoline 3a to be the least active, while the other compounds including the different chloro derivatives exhibited only intermediate activity.
• Werbel L. M., Kesten S. J., Turner W. R., Eur. J. Med. Chem, 28 (1993) N 11, S 837-852
  作者：Werbel L. M., Kesten S. J., Turner W. R.

  DOI：——

  日期：——