6-methoxy-2-(4,5,6-trimethoxy-indol-1-yl)-quinoline | 1334752-54-3

• 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: 6-methoxy-2-(4,5,6-trimethoxy-indol-1-yl)-quinoline
• 英文别名: 6-Methoxy-2-(4,5,6-trimethoxyindol-1-yl)quinoline
• CAS: 1334752-54-3
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: HLZSZPSMLWCZKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯-6-甲氧基喹啉 、 4,5,6-三甲氧基-1H-吲哚 在 caesium carbonate 、 copper(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以43%的产率得到6-methoxy-2-(4,5,6-trimethoxy-indol-1-yl)-quinoline
  参考文献：
  名称：

  Synthesis and biological evaluation of 1-(4′-Indolyl and 6′-Quinolinyl) indoles as a new class of potent anticancer agents

  摘要：

  A novel series of the biheterocycles-based compounds with core structure distinguished from combretastatin A-4 (1) and colchicine (5) have been synthesized and evaluated as potent anti-mitotic agents. Compound 1-(4'-Indolyl and 6'-quinolinyl)-4,5,6-trimethoxyindoles 13 and 19 showed substantial anti-proliferative activity against various human cancer cell lines, regardless to the tissue origin and the expression of multiple-drug resistance MDR1, with a mean IC50 value of 38 and 24 nM respectively. Compound 13 (IC50 = 1.7 mu M) also exhibited similar anti-tubulin activities to 1 (IC50 = 1.8 mu M) and displayed strong binding property to the colchicine binding site on the microtubules. Computational modeling analysis revealed that the binding mechanism of compound 13 is similar to that of CA4. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.065

文献信息

• Synthesis and biological evaluation of 1-(4′-Indolyl and 6′-Quinolinyl) indoles as a new class of potent anticancer agents
  作者：Mei-Jung Lai、Jang-Yang Chang、Hsueh-Yun Lee、Ching-Chuan Kuo、Mei-Hsiang Lin、Hsing-Pang Hsieh、Chi-Yen Chang、Jian-Sung Wu、Su-Ying Wu、Kuang-Shing Shey、Jing-Ping Liou

  DOI：10.1016/j.ejmech.2011.04.065

  日期：2011.9

  A novel series of the biheterocycles-based compounds with core structure distinguished from combretastatin A-4 (1) and colchicine (5) have been synthesized and evaluated as potent anti-mitotic agents. Compound 1-(4'-Indolyl and 6'-quinolinyl)-4,5,6-trimethoxyindoles 13 and 19 showed substantial anti-proliferative activity against various human cancer cell lines, regardless to the tissue origin and the expression of multiple-drug resistance MDR1, with a mean IC50 value of 38 and 24 nM respectively. Compound 13 (IC50 = 1.7 mu M) also exhibited similar anti-tubulin activities to 1 (IC50 = 1.8 mu M) and displayed strong binding property to the colchicine binding site on the microtubules. Computational modeling analysis revealed that the binding mechanism of compound 13 is similar to that of CA4. (C) 2011 Elsevier Masson SAS. All rights reserved.