1,4-bis(di(5-bromo-1H-indol-3-yl)methyl)benzene | 1359085-85-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1,4-bis(di(5-bromo-1H-indol-3-yl)methyl)benzene
• 英文别名: 1,4-bis(bis(5-bromo-1H-indol-3-yl)methyl)benzene；3-[[4-[bis(5-bromo-1H-indol-3-yl)methyl]phenyl]-(5-bromo-1H-indol-3-yl)methyl]-5-bromo-1H-indole
• CAS: 1359085-85-0
• 化学式: C₄₀H₂₆Br₄N₄
• 分子量: 882.289
• InChiKey: PJAPMGSDHIYRGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  48
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.2
• 氢给体数：
  4
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 对苯二甲醛 在 Ru-exchanged montmorillonite 作用下， 以77 %的产率得到1,4-bis(di(5-bromo-1H-indol-3-yl)methyl)benzene
  参考文献：
  名称：

  钌交换蒙脱土作为双（吲哚基）甲烷合成的高效且可重复使用的催化剂

  摘要：

  系统地探索了钌（Ru）交换蒙脱土（一种成熟的多相催化剂）的催化功效，以合成各种双（吲哚基）甲烷。所开发的方法始终以令人满意的收率产生所需的产物，而所提出的方法的显着优点包括最短的反应时间和无溶剂条件。此外，该方法的特点是程序简单、催化剂合成容易、从商业来源容易获得起始材料以及催化剂可回收的潜力。

  DOI：

  10.1007/s13738-024-03038-2

文献信息

• An efficient and practical synthesis of bis(indolyl)methanes catalyzed by N-sulfonic acid poly(4-vinylpyridinium) chloride
  作者：Frahad Shirini、Nader Ghaffari Khaligh、Omid Goli Jolodar

  DOI：10.1016/j.dyepig.2013.03.003

  日期：2013.8

  A mild, simple and convenient procedure for the synthesis of bis(indolyl)methane derivatives was described using N-sulfonic acid poly(4-vinylpyridinium) chloride as an efficient, cheap, and reusable catalyst under mild conditions.

  描述了使用N-磺酸聚（4-乙烯基吡啶）氯化物作为温和条件下的有效，廉价和可重复使用的催化剂的温和，简单和方便的合成双（吲哚基）甲烷衍生物的方法。
• PEG-SO₃H as a Catalyst for the Preparation of Bis-Indolyl and Tris-Indolyl Methanes in Aqueous Media
  作者：V. Jhansi Rani、K. Veena Vani、C. Venkata Rao

  DOI：10.1080/00397911.2010.551700

  日期：2012.7.15

  Abstract A facile, efficient, and green synthesis of bis-indolyl and tris-indolyl methanes has been developed by one-pot condensation of indole with structurally diverse aldehydes and ketones in the presence of poly(ethylene glycol)–bound sulfonic acid as catalyst at room temperature. GRAPHICAL ABSTRACT

  摘要 在聚（乙二醇）结合的磺酸作为催化剂存在下，通过吲哚与结构不同的醛和酮的一锅缩合，开发了一种简便、高效和绿色的双吲哚和三吲哚甲烷合成方法。室内温度。图形概要
• Two novel binuclear sulfonic-functionalized ionic liquids: Influence of anion and carbon-spacer on catalytic efficiency for one-pot synthesis of bis(indolyl)methanes
  作者：Nader Ghaffari Khaligh、Taraneh Mihankhah、Mohd Rafie Johan、Juan Joon Ching

  DOI：10.1016/j.molliq.2018.03.044

  日期：2018.6

  from pyrazinium, piperazinium, benzimidazolium, imidazolium mono- or di-cation containing chloride and hydrogen sulfate as counter anion under optimized conditions. It was proved that the new ionic liquids containing two sulfonic imidazole moieties with four-carbon spacer as well as hydrogen sulfate as acidic counter anion were superior to the previously reported ionic liquids.

  合成了两种新的具有四碳间隔基的双核磺酸官能化离子液体，并通过FTIR，MS，1 H和13对其结构进行了表征1 H NMR; 然后确定特定任务的新型离子液体水溶液的一些物理性质和pH值。研究了它们在温和条件下的双溶剂催化活性，以合成双（吲哚基）甲烷。在优化的条件下，将这些离子液体的催化活性与衍生自吡嗪鎓，哌嗪鎓，苯并咪唑鎓，咪唑鎓单或二阳离子的氯化物和硫酸氢盐作为抗衡阴离子的某些离子液体进行了比较。事实证明，含有两个带有四个碳间隔基的磺酸咪唑部分以及硫酸氢盐作为酸性抗衡阴离子的新型离子液体优于以前报道的离子液体。
• Synthesis and Evaluation of the Cytotoxicities of Tetraindoles: Observation that the 5-Hydroxy Tetraindole (SK228) Induces G₂ Arrest and Apoptosis in Human Breast Cancer Cells
  作者：Wen-Shan Li、Chie-Hong Wang、Shengkai Ko、Tzu Ting Chang、Ya Ching Jen、Ching-Fa Yao、Shivaji V. More、Shu-Chuan Jao

  DOI：10.1021/jm2013425

  日期：2012.2.23

  Current chemical and biological interest in indole-3-carbinol (I3C) and its metabolites has resulted in the discovery of new biologically active indoles. As part of a program aimed at the development of indole analogues, tetraindoles 1-15 were prepared and their antiproliferative effects on human breast cancer cells were evaluated. The results show that the 5-hydroxy-tetraindole 8 (SK228) has optimum antiproliferative activity against breast adenocarcinoma (MCF 7 and MDA-MB-231) cells and that this activity involves G(2)-phase arrest of the cell cycle with a distinctive increase in the expression of cyclin B1 and phospho-cdc2. Further observations suggest that 5-hydroxy-tetraindole 8 induces apoptosis through externalization of membrane phosphatidylserine, DNA fragmentation, and activation of caspase-3. Given the fact that I3C and its metabolites have been shown to improve therapeutic efficacy and to have a broad range of antitumor activities in human cancer cells, the current findings have important pharmacological relevance as they open a promising route to the development of a potential chemotherapeutic application of tetraindoles as agents for the treatment of breast cancer.