2,3-bis[2-(4-chlorophenyl)ethenyl]-1H-indole | 1330539-89-3

• 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: 2,3-bis[2-(4-chlorophenyl)ethenyl]-1H-indole
• CAS: 1330539-89-3
• 化学式: C₂₄H₁₇Cl₂N
• 分子量: 390.312
• InChiKey: HFOODGLJBVXKRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.79
• 氢给体数：
  1.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2,3-bis[2-(4-chlorophenyl)ethenyl]-1H-indole 在 palladium 10% on activated carbon 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以88%的产率得到2,3-bis(4-chlorophenyl)-9H-carbazole
  参考文献：
  名称：

  Unprecedented C-2 arylation of indole with diazonium salts: Syntheses of 2,3-disubstituted indoles and their antimicrobial activity

  摘要：

  A novel reaction of indole with aryldiazonium salts leading to the formation of 2-aryl-3-(arylazo)indoles was discovered. The products were found to possess potent anti-MRSA and anti-LLVRE activities. The SAR studies indicate that the potentially metabolically labile azo functionality can be replaced with ether oxygen and thioether sulfur atoms without any loss of activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.081
• 作为产物：
  描述：

  吲哚 、 4-氯苯乙烯 在 copper diacetate 、 palladium diacetate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 以41%的产率得到2,3-bis[2-(4-chlorophenyl)ethenyl]-1H-indole
  参考文献：
  名称：

  Photoactivated 2,3-distyrylindoles kill multi-drug resistant bacteria

  摘要：

  Compounds based on the 2,3-distyrylindole scaffold were found to exhibit bactericidal properties upon irradiation with white light. At the concentration of 1 mu M, the lead compound 1 completely (ca. 10(9) CFU/mL) eradicated such Gram-positive organisms as S. aureus (MRSA, MSSA), E. faecalis (VRE), S. pyogenes and S. mutans when irradiated with white light for 2 min. At the concentration of 5 mu L and in the presence of polymyxin E at non-bactericidal 1.25 mu g/mL concentration, 1 also showed a 7-log to 9-log reductions in bacterial counts of such Gram-negative organisms as multi-drug resistant (MDR) A baumannii, MDR P. aeruginosa, E. coll and Klebsiella pneumoniae (CRE: KPC and NDM-1), also when irradiated with white light for 2 mm The structure-activity relationship studies revealed that unsubstituted at benzene rings 2,3-distyrylindole 2 was most potent and gave a 5-order of magnitude eradication of a MRSA strain at the concentration of 30 nM upon irradiation with white light. Initial mechanistic experiments revealed the disruption of bacterial cell membrane, but indicated that singlet oxygen production, which is commonly associated with photodynamic therapy, may not play a role in the bactericidal effects of the 2,3-distyryhndoles. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.04.001