11-methyl-6H-indolo[2,3-b] quinolin-9-ol | 1402935-83-4

• 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: 11-methyl-6H-indolo[2,3-b] quinolin-9-ol
• 英文别名: 11-methyl-6H-indolo[2,3-b]quinolin-9-ol
• CAS: 1402935-83-4
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: WKQXASHTUQDQNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 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：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11-methyl-6H-indolo[2,3-b] quinolin-9-ol 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 6.08h， 生成
  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：

  9-methoxy-11-methyl-6H-indolo[2,3-b]quinoline 在 氢溴酸 、 溶剂黄146 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 12.0h， 以53%的产率得到11-methyl-6H-indolo[2,3-b] quinolin-9-ol
  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

• HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-<i>b</i>]quinolines &amp; related natural products
  作者：Auqib Rashid、Waseem I. Lone、Preeti Dogra、Showkat Rashid、Bilal A. Bhat

  DOI：10.1039/d4ob00414k

  日期：——

  An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3-b]quinolines is reported. This protocol, executed in aqueous HFIP has broad substrate scope and is well inclined towards the ideas of sustainable chemistry. Applications of these strategies in accessing bioactive natural products like vibrindole, norcryptotakeine, neocryptolepine and indenoindolone scaffolds

  报道了吲哚的快速无金属 C-3 烷基化及其 NIS 介导的吲哚并[2,3- b ]喹啉的偏离。该协议在水性 HFIP 中执行，具有广泛的底物范围，并且非常倾向于可持续化学的理念。这些策略在获取生物活性天然产物（如 vibrindole、norcryptotakeine、neocryptolepine 和茚并吲哚酮支架）方面的应用也已得到证实。
• 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.