6-[2-(diethylamino)ethyl]-6H-indolo[2,3-b]quinoxaline | 59184-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-[2-(diethylamino)ethyl]-6H-indolo[2,3-b]quinoxaline
• 英文别名: 6-(2-diethylamino)ethyl-6H-indolo[2,3-b]quinoxaline；diethyl(2-indolo[2,3-b]quinoxalin-6-ylethyl)amine；diethyl-(2-indolo[2,3-b]quinoxalin-6-yl-ethyl)-amine；Diethyl-(2-indolo[2,3-b]quinoxalin-6-yl-ethyl)-amine；N,N-diethyl-2-indolo[3,2-b]quinoxalin-6-ylethanamine
• CAS: 59184-53-1
• 化学式: C₂₀H₂₂N₄
• mdl: MFCD02233043
• 分子量: 318.421
• InChiKey: FPWJYPHBDVQSKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 在 四丁基碘化铵 、 potassium carbonate 、 溶剂黄146 、 potassium hydroxide 作用下， 反应 60.0h， 生成 6-[2-(diethylamino)ethyl]-6H-indolo[2,3-b]quinoxaline
  参考文献：
  名称：

  6H-吲哚并[2,3-b]喹喔啉类化合物及其制备方法和应用

  摘要：

  本发明提供了一种6H‑吲哚并[2,3‑b]喹喔啉衍生物及其制备方法和应用，通式为，制备方法是以邻苯二胺、吲哚二酮、二卤代烷烃及胺类化合物为原料来合成6H‑吲哚并[2,3‑b]喹喔啉衍生物，且这类化合物表现出了良好的抗肿瘤活性。

  公开号：

  CN110540541A

文献信息

• Synthesis of an Indoloquinoxaline Derivative as Potential Inhibitor of InhA enzyme of Mycobacterium tuberculosis
  作者：Asmae Zanzoul、Aurélien Chollet、Estefania Piedra-Arroni、Jean-Luc Stigliani、Vania Bernardes-Génisson、El Mokhtar Essassi、Geneviève Pratviel

  DOI：10.2174/1570178612666150924000909

  日期：2015.11.2

  Seven heterocyclic compounds derived from isatin have been synthesized. Isatin was N-substituted with four aromatic/aliphatic and benzylic moieties (1a-d). Compounds 1a-c were condensed with o-phenylenediamine to afford indoloquinoxaline derivatives (2a-c). Products were tested as inhibitors of InhA enzyme of M. tuberculosis. Compound 6-(diethylaminoethyl)indoloquinoxaline (2a) inhibited 38% of InhA activity at 50 µM. The possible modes of interaction of 2a with InhA were explored by molecular docking. Docking experiments afford keys to improve compound 2a for the design of new potential active drugs against tuberculosis.

  已合成七种来源于靛红（Isatin）的杂环化合物。靛红进行了N-取代，引入了四种芳香/脂肪族和苄基部分（1a-d）。化合物1a-c与邻苯二胺缩合，得到了吲哚喹唑啉衍生物（2a-c）。这些产物被测试为结核分枝杆菌InhA酶的抑制剂。6-（二乙氨基乙基）吲哚喹唑啉（2a）在50 µM浓度下抑制了InhA活性的38%。通过分子对接研究了2a与InhA可能的相互作用方式。对接实验为改进化合物2a，以设计新的潜在抗结核活性药物提供了关键信息。
• Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines
  作者：Marina O. Shibinskaya、Sergey A. Lyakhov、Alexander V. Mazepa、Sergey A. Andronati、Alexander V. Turov、Nadezhda M. Zholobak、Nikolay Ya. Spivak

  DOI：10.1016/j.ejmech.2009.12.014

  日期：2010.3

  New 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines were synthesized with high yields using bromoethylisatin and 6-(2-bromoethyl)-6H-indolo[2,3-b]quinoxaline as intermediates. These compounds were screened for the cytotoxicity, antiviral activity and interferon inducing ability. it was shown, that tested 6-(2-aminoethyl)-6H-indolo[2,3-b]quinoxalines are low toxic potent interferon inducers and antivirals. Morpholine and 4-methyl-piperidine derivatives appeared as the most active antivirals and the least cytotoxic in the investigated series. (C) 2009 Elsevier Masson SAS. All rights reserved.
• KNOTZ F.; WENDELIN W., SCI. PHARM. <SCPH-A4>, 1975, 43, NO 4, 249-260
  作者：KNOTZ F.、 WENDELIN W.

  DOI：——

  日期：——
• INHIBITION OF NF-KB
  申请人：Gudkov Andrei V.

  公开号：US20090099191A1

  公开（公告）日：2009-04-16

  The present invention is generally related to the modulation of cell growth or apoptosis. Compositions for modulating cell growth or apoptosis, methods of use thereof, and methods of identification thereof are described.