6-(2-dimethylaminoethyl)-11-methyl-9-nitro-6H-indolo[2,3-b]quinoline | 1402935-87-8

• 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: 6-(2-dimethylaminoethyl)-11-methyl-9-nitro-6H-indolo[2,3-b]quinoline
• 英文别名: N,N-dimethyl-2-(11-methyl-9-nitroindolo[2,3-b]quinolin-6-yl)ethanamine
• CAS: 1402935-87-8
• 化学式: C₂₀H₂₀N₄O₂
• 分子量: 348.404
• InChiKey: MMFHMWKLKZAVRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-dimethylaminoethyl)-11-methyl-9-nitro-6H-indolo[2,3-b]quinoline 在 吡啶 、 盐酸 、 硫酸 、 四丁基溴化铵 、 potassium carbonate 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 N-[6-(2-dimethylaminoethyl)-11-methyl-6H-indolo[2,3-b]quinol-9-yl]-N-(2-dimethylaminoethyl)-p-toluenesulfonamide
  参考文献：
  名称：

  New derivatives of 11-methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as cytotoxic DNA topoisomerase II inhibitors

  摘要：

  Novelindolo[2,3-b]quinoline derivatives substituted at N-6 and C-2 or C-9 positions with (dimethylamino) ethyl chains linked to heteroaromatic core by ether, amide or amine bonds, were manufactured and evaluated in vitro for their cytotoxic activity against several cell lines of different origin including multidrug resistant sublines and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. It was found, that all compounds show cytotoxic activity against cell lines tested, including multidrug resistant LoVo/DX, MES-SA/DX5 and HL-60 sublines. The tested compounds induce the G(2)M phase cell cycle arrest in Jurkat cells, and inhibit topoisomerase II activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.032
• 作为产物：
  描述：

  二甲氨基氯乙烷盐酸 、 11-methyl-9-nitro-6H-indolo[2,3-b]quinoline 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 5.0h， 以27%的产率得到6-(2-dimethylaminoethyl)-11-methyl-9-nitro-6H-indolo[2,3-b]quinoline
  参考文献：
  名称：

  New derivatives of 11-methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as cytotoxic DNA topoisomerase II inhibitors

  摘要：

  Novelindolo[2,3-b]quinoline derivatives substituted at N-6 and C-2 or C-9 positions with (dimethylamino) ethyl chains linked to heteroaromatic core by ether, amide or amine bonds, were manufactured and evaluated in vitro for their cytotoxic activity against several cell lines of different origin including multidrug resistant sublines and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. It was found, that all compounds show cytotoxic activity against cell lines tested, including multidrug resistant LoVo/DX, MES-SA/DX5 and HL-60 sublines. The tested compounds induce the G(2)M phase cell cycle arrest in Jurkat cells, and inhibit topoisomerase II activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.032

文献信息

• New derivatives of 11-methyl-6-[2-(dimethylamino)ethyl]-6H-indolo[2,3-b]quinoline as cytotoxic DNA topoisomerase II inhibitors
  作者：Wojciech Luniewski、Joanna Wietrzyk、Joanna Godlewska、Marta Switalska、Malgorzata Piskozub、Wanda Peczynska-Czoch、Lukasz Kaczmarek

  DOI：10.1016/j.bmcl.2012.08.032

  日期：2012.10

  Novelindolo[2,3-b]quinoline derivatives substituted at N-6 and C-2 or C-9 positions with (dimethylamino) ethyl chains linked to heteroaromatic core by ether, amide or amine bonds, were manufactured and evaluated in vitro for their cytotoxic activity against several cell lines of different origin including multidrug resistant sublines and tested for their ability to influence the cell cycle and inhibit topoisomerase II activity. It was found, that all compounds show cytotoxic activity against cell lines tested, including multidrug resistant LoVo/DX, MES-SA/DX5 and HL-60 sublines. The tested compounds induce the G(2)M phase cell cycle arrest in Jurkat cells, and inhibit topoisomerase II activity. (C) 2012 Elsevier Ltd. All rights reserved.