2,3,5-tribromo-6-[2-(4-methylphenyl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione | 1394077-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3,5-tribromo-6-[2-(4-methylphenyl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
• CAS: 1394077-19-0
• 化学式: C₂₁H₁₂Br₃NO₂
• 分子量: 550.044
• InChiKey: LYWHFPDZVMKCIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-甲氧基-2-甲基吲哚 、 2,3,5-tribromo-6-[2-(4-methylphenyl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以28%的产率得到2,5-dibromo-3-(5-methoxy-2-methyl-1H-indol-3-yl)-6-[2-(4-methylphenyl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Synthesis and anti-breast cancer activity of new indolylquinone derivatives

  摘要：

  A series of novel indolylquinones have been synthesized by treating halogeno-quinone with 2-substituated indole derivatives in the presence of kalium carbonate and TEBA in acetonitrile at room temperature. These compounds were evaluated for their antiproliferative activity against human MDA-MB-231 and MCF-7 breast cancer cell lines. All the tested compounds showed potent mircomolar cytotoxicity activity in both breast cancer cell lines. 3d (IC50 value = 2.29 mu g/mL for MCF-7 cells) and 3g (IC50 value = 3.99 mu g/mL for MDA-MB-231 cells) displayed the most potent antiproliferative activity of the series. Also, in vitro anticancer activity of the compounds further showed that bis-indolylquinones were more active than mono-indolylquinones. Fluorescence microscopy analysis indicated that compound 3d and 3g inhibited breast cancer cells proliferation by triggering apoptotic cell death. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.019
• 作为产物：
  描述：

  2-(4-甲基苯基)-1H-吲哚 、 四溴对苯醌 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以77%的产率得到2,3,5-tribromo-6-[2-(4-methylphenyl)-1H-indol-3-yl]cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Synthesis and anti-breast cancer activity of new indolylquinone derivatives

  摘要：

  A series of novel indolylquinones have been synthesized by treating halogeno-quinone with 2-substituated indole derivatives in the presence of kalium carbonate and TEBA in acetonitrile at room temperature. These compounds were evaluated for their antiproliferative activity against human MDA-MB-231 and MCF-7 breast cancer cell lines. All the tested compounds showed potent mircomolar cytotoxicity activity in both breast cancer cell lines. 3d (IC50 value = 2.29 mu g/mL for MCF-7 cells) and 3g (IC50 value = 3.99 mu g/mL for MDA-MB-231 cells) displayed the most potent antiproliferative activity of the series. Also, in vitro anticancer activity of the compounds further showed that bis-indolylquinones were more active than mono-indolylquinones. Fluorescence microscopy analysis indicated that compound 3d and 3g inhibited breast cancer cells proliferation by triggering apoptotic cell death. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.019

文献信息

• Synthesis and anti-breast cancer activity of new indolylquinone derivatives
  作者：Xue Li、Shi-Long Zheng、Xian Li、Ju-Lian Li、Ou Qiang、Rui Liu、Ling He

  DOI：10.1016/j.ejmech.2012.04.019

  日期：2012.8

  A series of novel indolylquinones have been synthesized by treating halogeno-quinone with 2-substituated indole derivatives in the presence of kalium carbonate and TEBA in acetonitrile at room temperature. These compounds were evaluated for their antiproliferative activity against human MDA-MB-231 and MCF-7 breast cancer cell lines. All the tested compounds showed potent mircomolar cytotoxicity activity in both breast cancer cell lines. 3d (IC50 value = 2.29 mu g/mL for MCF-7 cells) and 3g (IC50 value = 3.99 mu g/mL for MDA-MB-231 cells) displayed the most potent antiproliferative activity of the series. Also, in vitro anticancer activity of the compounds further showed that bis-indolylquinones were more active than mono-indolylquinones. Fluorescence microscopy analysis indicated that compound 3d and 3g inhibited breast cancer cells proliferation by triggering apoptotic cell death. (C) 2012 Elsevier Masson SAS. All rights reserved.