3-chloro-6H-indolo[2,3-b]quinoline | 1150313-11-3

• 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-6H-indolo[2,3-b]quinoline
• CAS: 1150313-11-3
• 化学式: C₁₅H₉ClN₂
• 分子量: 252.703
• InChiKey: LTDAVZSQEZTXLA-UHFFFAOYSA-N

物化性质

• 沸点：
  496.4±25.0 °C(predicted)
• 密度：
  1.441±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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-6H-indolo[2,3-b]quinoline 、 碘甲烷 以 四氢呋喃 为溶剂， 生成 3-chloro-5-methyl-5H-indolo[2,3-b]quinoline hydroiodide
  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
• 作为产物：
  描述：

  (Z)-3-(2-bromo-4-chlorophenyl)-2-(2-nitrophenyl)acrylonitrile 在 盐酸 、 四(三苯基膦)钯 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 3-chloro-6H-indolo[2,3-b]quinoline
  参考文献：
  名称：

  钯催化的双重环空法：去甲隐油菜碱的合成方法

  摘要：

  报道了一种新型的钯催化双环合反应合成壬基隐油菜碱衍生物的新方法，该过程涉及两个中心杂环的协同构建。去甲隐油菜籽进一步的甲基化以提供其生物碱类似物新隐油菜籽暗示了各种新隐油菜籽衍生物的合成是可行的。根据机理研究表明，Pd（0）的氧化加成是激活腈分子内加成的关键步骤。

  DOI：

  10.1021/acs.orglett.9b00287

文献信息

• Materials for organic electroluminescent devices
  申请人：Merck Patent GmbH

  公开号：US10923665B2

  公开（公告）日：2021-02-16

  The present invention relates to compounds suitable for use in electronic devices, and to electronic devices, especially organic electroluminescent devices, comprising these compounds.

  本发明涉及适用于电子设备的化合物，以及包括这些化合物的电子设备，特别是有机电致发光器件。
• 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.
• MATERIALIEN FÜR ORGANISCHE ELEKTROLUMINESZENZVORRICHTUNGEN
  申请人：Merck Patent GmbH

  公开号：EP3583104B1

  公开（公告）日：2021-06-09
• MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES
  申请人：Merck Patent GmbH

  公开号：US20200044162A1

  公开（公告）日：2020-02-06

  The present invention relates to compounds suitable for use in electronic devices, and to electronic devices, especially organic electroluminescent devices, comprising these compounds.
• Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine
  作者：Li-Hsuan Yeh、Hung-Kai Wang、Gangaram Pallikonda、Yu-Lun Ciou、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.9b00287

  日期：2019.3.15

  Pd-catalyzed dual annulation reaction to synthesize the norneocryptolepine derivatives involving the concerted construction of two central heterocycles is reported. The further methylation of the norneocryptolepine to afford its alkaloid analog neocryptolepine implies that synthesis of various neocryptolepine derivatives is feasible. The oxidative addition of Pd(0) is indicated as the key step to activate the

  报道了一种新型的钯催化双环合反应合成壬基隐油菜碱衍生物的新方法，该过程涉及两个中心杂环的协同构建。去甲隐油菜籽进一步的甲基化以提供其生物碱类似物新隐油菜籽暗示了各种新隐油菜籽衍生物的合成是可行的。根据机理研究表明，Pd（0）的氧化加成是激活腈分子内加成的关键步骤。