5-bromo-3-((5-bromo-1-pentyl-1H-indol-3-yl)(4-fluorophenyl)methyl)-1-pentyl-1H-indole | 1450624-87-9

• 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-((5-bromo-1-pentyl-1H-indol-3-yl)(4-fluorophenyl)methyl)-1-pentyl-1H-indole
• 英文别名: 5-Bromo-3-[(5-bromo-1-pentylindol-3-yl)-(4-fluorophenyl)methyl]-1-pentylindole；5-bromo-3-[(5-bromo-1-pentylindol-3-yl)-(4-fluorophenyl)methyl]-1-pentylindole
• CAS: 1450624-87-9
• 化学式: C₃₃H₃₅Br₂FN₂
• 分子量: 638.461
• InChiKey: MBJKZSQFMUAFJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-溴吲哚 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 5-bromo-3-((5-bromo-1-pentyl-1H-indol-3-yl)(4-fluorophenyl)methyl)-1-pentyl-1H-indole
  参考文献：
  名称：

  Fe/Al pillared clay catalyzed solvent-free synthesis of bisindolylmethanes using diversely substituted indoles and carbonyl compounds

  摘要：

  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。

  DOI：

  10.1039/c2ra22258b

文献信息

• 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。
• 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.