4,5,6-Trimethoxy-1-(4-methoxy-2-nitrophenyl)indole | 1334752-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,5,6-Trimethoxy-1-(4-methoxy-2-nitrophenyl)indole
• CAS: 1334752-59-8
• 化学式: C₁₈H₁₈N₂O₆
• 分子量: 358.351
• InChiKey: OSQRXCQCXRTNBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5,6-Trimethoxy-1-(4-methoxy-2-nitrophenyl)indole 在 铁粉 、 氯化铵 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以49%的产率得到5-methoxy-2-(4,5,6-trimethoxy-indol-1-yl)-phenylamine
  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
• 作为产物：
  描述：

  4,5,6-三甲氧基-1H-吲哚 、 4-碘基-3-硝基苯甲醚 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14%的产率得到4,5,6-Trimethoxy-1-(4-methoxy-2-nitrophenyl)indole
  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