5-bromo-3-(1-(5-bromo-1H-indol-3-yl)butyl)-1H-indole | 1314695-33-4

• 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: 5-bromo-3-(1-(5-bromo-1H-indol-3-yl)butyl)-1H-indole
• 英文别名: 3,3'-(butane-1,1-diyl)bis(5-bromo-1H-indole)；3,3'-(but-1,1-diyl)bis(5-bromo-1H-indole)；5-bromo-3-[1-(5-bromo-1H-indol-3-yl)butyl]-1H-indole
• CAS: 1314695-33-4
• 化学式: C₂₀H₁₈Br₂N₂
• 分子量: 446.184
• InChiKey: GYLNNZSOTKUCRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 三正丁胺 在 copper diacetate 、 palladium diacetate 作用下， 反应 12.0h， 以62%的产率得到5-bromo-3-(1-(5-bromo-1H-indol-3-yl)butyl)-1H-indole
  参考文献：
  名称：

  钯通过叔胺的脂肪族C–H键活化催化吲哚烷基化

  摘要：

  吲哚的烷基化是通过Pd催化叔胺与吲哚偶联的脂肪族C–H键活化，再与吲哚偶联，然后进行C–N键裂解，然后再添加吲哚。该方法涉及烷烃链从叔胺迁移到吲哚。

  DOI：

  10.1016/j.tetlet.2011.04.110

文献信息

• Seralite SRC-120 resin catalyzed synthesis of bis(indolyl)methanes using indoles and low/high boiling point carbonyl compounds under solvent free conditions
  作者：Harish K. Indurthi、Reena Virdi、Papita Koli、Desaboini Nageswara Rao、Deepak K Sharma

  DOI：10.1080/00397911.2020.1849724

  日期：2021.1.2

  Abstract A highly inexpensive, and operationally simple seralite SRC-120 (strongly acidic cation exchange resin) catalyzed synthesis of 3,3′-bis(indolyl)methanes (BIMs) from indoles and low/high boiling point carbonyl compounds under solvent-free condition is reported. Synthesis of BIMs with low boiling point carbonyls at room temperature takes prolonged reaction time and give low yields at high temperature

  摘要 在无溶剂条件下，由吲哚和低/高沸点羰基化合物合成的3,3'-双（吲哚基）甲烷（BIM）的合成反应非常便宜，并且操作简单，是一种Seralite SRC-120（强酸性阳离子交换树脂）。报告。在室温下合成具有低沸点羰基的BIM会延长反应时间，并且在高温下产率较低。报道的方法克服了这些限制，并且在微波辐射条件下以较短/较短的反应时间（5-10分钟）与低/高沸点醛/酮一起使用时效果显着，并提供中等至极好的收率（65-94％）。而且，催化剂至少可循环使用五次而活性没有明显损失，这使整个过程具有吸引力且绿色环保。
• Fe/Al pillared clay catalyzed solvent-free synthesis of bisindolylmethanes using diversely substituted indoles and carbonyl compounds
  作者：Deepak K. Sharma、Altaf Hussain、Mallikharjuna Rao Lambu、Syed Khalid Yousuf、Sudip Maiety、Baldev Singh、Debaraj Mukherjee

  DOI：10.1039/c2ra22258b

  日期：——

  A fast, solvent-free solid acid mediated synthetic strategy for the synthesis of bisindolylmethanes has been developed. The process is applicable to a wide range of substrates with different protecting group survival properties. Reusability of Fe/Al pillared clay for more than 5 cycles without significant loss of catalytic activity adds to the features of the reaction.

  我们开发了一种快速、无溶剂的固体酸介导合成双吲哚甲烷的方法。该工艺适用于多种具有不同保护基团存活特性的底物。铁/铝柱状粘土可重复使用 5 次以上而不会明显丧失催化活性，这也是该反应的一大特点。
• Natural Products for Biocides Discovery: Discovery of Arundine and It’s Derivatives as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents
  作者：Ziwen Wang、Qingmin Wang、Ancai Liao、Shengli Jin

  DOI：10.3987/com-19-14192

  日期：——

  Plant diseases are one of the natural disasters that seriously harm agricultural production, and it is very difficult to control. The discovery of new antiviral and antifungal lead compounds becomes more and more important. Natural product arundine was found to have anti-tobacco mosaic virus (TMV) activity and anti-phytopathogenic-fungus activity for the first time. A series of arundine analogues were designed, synthesized and evaluated for their antiviral and fungicidal activities. Compound 6 with excellent antiviral activity emerged as novel antiviral lead compound. Compound 7 with 12.6-38.3 mu g/mL EC50 values against 14 plant pathogens emerged as novel antifungal lead compound. This work laid a foundation for promoting the application of arundine analogues in plant protection.
• A new class of bactericidal agents against S. aureus, MRSA and VRE derived from bisindolylmethane
  作者：Deepak K. Sharma、Anil K. Tripathi、Rashmi Sharma、Reena Chib、Reyaz ur Rasool、Altaf Hussain、Baldev Singh、Anindya Goswami、Inshad A. Khan、Debaraj Mukherjee

  DOI：10.1007/s00044-013-0764-4

  日期：2014.4

  A series of bisindolylmethanes (BIMs) (1a-7j) including hybrid BIMs 6a-6c were prepared for bioevaluation. The results of initial antimicrobial screening of compounds 1a-6c showed compounds 2b, 2m, 4a and 5b to be the most potent inhibitors, exhibiting MIC as well as MBC values equal to or less than that of ciprofloxacin (0.5-2 mu g/mL) against Staphylococcus aureus, MRSA and VRE. Compound 2m was selected further to study the effect of N,N' disubstitution towards antibacterial and antitumor activity. It was observed that substitution at N,N' position (7a-7j) of 2m diminishes its antibacterial activity though in vitro antitumour activity against a panel of prostate, cervical and lung cancer cell lines remains more or less intact.