2,5-dibromo-3,6-bis(2-methyl-1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione | 1394077-35-0

• 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: 2,5-dibromo-3,6-bis(2-methyl-1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione
• 英文别名: 2,5-dibromo-3,6-bis(2-methylindol-3-yl)-1,4-benzoquinone
• CAS: 1394077-35-0
• 化学式: C₂₄H₁₆Br₂N₂O₂
• 分子量: 524.211
• InChiKey: JJNFMHRVUBFIEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-甲基吲哚 、 2,5-二溴-1,4-苯醌 在 对甲苯磺酸 作用下， 以80 %的产率得到2,5-dibromo-3,6-bis(2-methyl-1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  通过无溶剂多键形成工艺一锅机械化学合成单-和双-吲哚基醌

  摘要：

  有趣的真菌：双吲哚基醌是真菌天然产物，具有有趣的药理特性。这里描述了一种用于合成吲哚基醌的新一锅机械化学方法，该方法通过多米诺迈克尔加成/氧化过程从吲哚和二卤醌开始，在 FeCl 3或p- TsOH 作为催化剂和 Fetizon 试剂作为氧化剂的存在下发生。

  DOI：

  10.1002/cssc.202101529

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.
• CN116924960
  申请人：——

  公开号：——

  公开（公告）日：——
• One‐Pot Mechanochemical Synthesis of Mono‐ and Bis‐Indolylquinones via Solvent‐Free Multiple Bond‐Forming Processes
  作者：Marta Piquero、Cristina Font、Natalia Gullón、Pilar López‐Alvarado、J. Carlos Menéndez

  DOI：10.1002/cssc.202101529

  日期：2021.11.4

  with fungi: Bis-indolylquinones are fungal natural products endowed with interesting pharmacological properties. Here a new one-pot mechanochemical methodology for the synthesis of indolylquinones is described, which takes place via domino Michael addition/oxidation processes starting from indoles and dihaloquinones in the presence of FeCl3 or p-TsOH as catalysts and Fetizon's reagent as an oxidant

  有趣的真菌：双吲哚基醌是真菌天然产物，具有有趣的药理特性。这里描述了一种用于合成吲哚基醌的新一锅机械化学方法，该方法通过多米诺迈克尔加成/氧化过程从吲哚和二卤醌开始，在 FeCl 3或p- TsOH 作为催化剂和 Fetizon 试剂作为氧化剂的存在下发生。