5-bromo-3-(1-(5-bromo-1H-indol-3-yl)nonyl)-1H-indole | 1454799-85-9

• 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-(1-(5-bromo-1H-indol-3-yl)nonyl)-1H-indole
• 英文别名: 3,3'-(nonan-1,1-diyl)-bis-(5-bromo-1H-indole)；5-bromo-3-[1-(5-bromo-1H-indol-3-yl)nonyl]-1H-indole
• CAS: 1454799-85-9
• 化学式: C₂₅H₂₈Br₂N₂
• 分子量: 516.319
• InChiKey: WHWIZHCYIFUUDA-UHFFFAOYSA-N

物化性质

• 沸点：
  629.4±50.0 °C(predicted)
• 密度：
  1.438±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 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 、 壬醛 在 Fe/Al pillared clay-425 °C 作用下， 以 neat (no solvent) 为溶剂， 以81%的产率得到5-bromo-3-(1-(5-bromo-1H-indol-3-yl)nonyl)-1H-indole
  参考文献：
  名称：

  A new class of bactericidal agents against S. aureus, MRSA and VRE derived from bisindolylmethane

  摘要：

  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.

  DOI：

  10.1007/s00044-013-0764-4

文献信息

• A Tandem Hydroformylation‐Organocatalyzed Friedel‐Crafts Reaction for the Synthesis of Diindolylmethanes
  作者：Lukas Miller、Felix Bauer、Bernhard Breit

  DOI：10.1002/chem.202400188

  日期：——

  Herein, a highly efficient and atom-economic tandem hydroformylation – organocatalyzed Friedel-Crafts reaction sequence for the synthesis of diindolylmethanes is presented. The synthesis of 21 derivatives with overall yields of up to 85 % showed that we were able to expand the range of readily accessible diidolylmethanes while demonstrating the utility of our presented method.

  在此，提出了一种高效且原子经济的串联加氢甲酰化 - 有机催化的傅克反应序列，用于合成二吲哚基甲烷。 21 种衍生物的合成总产率高达 85%，这表明我们能够扩大容易获得的二吲哚基甲烷的范围，同时证明我们提出的方法的实用性。
• 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.