4-(1-benzotriazolyl)-6-chloroquinoline | 854161-02-7

• 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: 4-(1-benzotriazolyl)-6-chloroquinoline
• 英文别名: 4-benzotriazol-1-yl-6-chloro-quinoline；4-Benzotriazol-1-yl-6-chlor-chinolin；4-(Benzotriazol-1-yl)-6-chloroquinoline；4-(benzotriazol-1-yl)-6-chloroquinoline
• CAS: 854161-02-7
• 化学式: C₁₅H₉ClN₄
• 分子量: 280.716
• InChiKey: SEPNQFZLEUQSOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(1-benzotriazolyl)-6-chloroquinoline 在 polyphosphoric acid 作用下， 以77%的产率得到2-chloro-11H-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
• 作为产物：
  描述：

  T406石油添加剂 、 4,6-二氯喹啉 反应 0.5h， 以77%的产率得到4-(1-benzotriazolyl)-6-chloroquinoline
  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

• 115. Attempts to find new antimalarials. Part XXIX. The synthesis of various derivatives of 2 : 3-benz-γ-carboline
  作者：William O. Kermack、Nora E. Storey

  DOI：10.1039/jr9500000607

  日期：——
• 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.