8-bromo-2-chloro-5-methyl-5H-indolo[3,2-c]quinoline | 1351085-73-8

• 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-bromo-2-chloro-5-methyl-5H-indolo[3,2-c]quinoline
• 英文别名: 8-bromo-2-chloroisocryptolepine；8-Bromo-2-chloro-5-methyl-indolo[3,2-c]quinoline；8-bromo-2-chloro-5-methylindolo[3,2-c]quinoline
• CAS: 1351085-73-8
• 化学式: C₁₆H₁₀BrClN₂
• 分子量: 345.626
• InChiKey: HLLMQAJIHXLHER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 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：

  N-tosyl-5-bromoindole 在 三氟甲磺酸 、 水 、 硝基苯 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 8-bromo-2-chloro-5-methyl-5H-indolo[3,2-c]quinoline
  参考文献：
  名称：

  Synthesis of isocryptolepine analogues and their structure–activity relationship studies as antiplasmodial and antiproliferative agents

  摘要：

  Novel isocryptolepine analogues have been conveniently synthesized and evaluated for antimalarial and antiproliferative activities. We have found 3-fluoro-8-bromo-isocryptolepine (1n) to have the highest activities against chloroquine-resistant chloroquine-sensitive 307, and chloroquine- and mefloquine-resistant SKF58 and SRIV35 strains. Several fluorine-substituted analogues (1b, 1n, and 1q) also showed excellent selectivities while maintaining good to excellent activities against all four Plasmodium falciparum strains. Additionally, antiproliferative properties of isocryptolepine derivatives against HepG2, HuCCA-1, MOLT-3 and A549 cancer cell lines are reported for the first time in this study. 2-Chloroisocryptolepine (1c) and benzo-fused-2-chloroisocryptolepine (1i) showed significant bioactivities whereas several novel fluorinated compounds and 2-chloro-8-bromoisocryptolepine (If) displayed excellent selectivities. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.047

文献信息

• 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.
• Synthesis of isocryptolepine analogues and their structure–activity relationship studies as antiplasmodial and antiproliferative agents
  作者：Pasuk Aroonkit、Charnsak Thongsornkleeb、Jumreang Tummatorn、Suppachai Krajangsri、Mathirut Mungthin、Somsak Ruchirawat

  DOI：10.1016/j.ejmech.2015.02.047

  日期：2015.4

  Novel isocryptolepine analogues have been conveniently synthesized and evaluated for antimalarial and antiproliferative activities. We have found 3-fluoro-8-bromo-isocryptolepine (1n) to have the highest activities against chloroquine-resistant chloroquine-sensitive 307, and chloroquine- and mefloquine-resistant SKF58 and SRIV35 strains. Several fluorine-substituted analogues (1b, 1n, and 1q) also showed excellent selectivities while maintaining good to excellent activities against all four Plasmodium falciparum strains. Additionally, antiproliferative properties of isocryptolepine derivatives against HepG2, HuCCA-1, MOLT-3 and A549 cancer cell lines are reported for the first time in this study. 2-Chloroisocryptolepine (1c) and benzo-fused-2-chloroisocryptolepine (1i) showed significant bioactivities whereas several novel fluorinated compounds and 2-chloro-8-bromoisocryptolepine (If) displayed excellent selectivities. (C) 2015 Elsevier Masson SAS. All rights reserved.