5-propyl-2-(4-methoxyphenyl)-1H-indole | 943439-42-7

• 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-propyl-2-(4-methoxyphenyl)-1H-indole
• 英文别名: 2-(4-methoxyphenyl)-5-n-propylindole；2-(4-methoxyphenyl)-5-propyl-1H-indole
• CAS: 943439-42-7
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: HRDCKNIPEJBTSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-propyl-2-(4-methoxyphenyl)-1H-indole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 3.0h， 以35%的产率得到2-(4-methoxyphenyl)-5-propyl-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

  摘要：

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.030
• 作为产物：
  描述：

  对丙基苯胺 、 alpha-溴-4-甲氧基苯乙酮 在 N,N-二甲基苯胺 作用下， 以 xylene 为溶剂， 以20%的产率得到5-propyl-2-(4-methoxyphenyl)-1H-indole
  参考文献：
  名称：

  Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

  摘要：

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.030

文献信息

• Antibacterial activity of a novel series of 3-bromo-4-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione derivatives – An extended structure–activity relationship study
  作者：Siavosh Mahboobi、Emerich Eichhorn、Matthias Winkler、Andreas Sellmer、Ute Möllmann

  DOI：10.1016/j.ejmech.2007.05.009

  日期：2008.3

  Compounds containing 3-bromo-2,5-dihydro-1H-2,5-pyrroledione and indole substructures were found to have antibacterial activity against resistant strains of Staphylococcus aureus and some other Gram positive bacteria. The investigated compounds exhibit minimal inhibition concentrations (MICs) lower than those of common antibiotics like vancomycin or ciprofloxacin. Activity against multiresistant strains suggests a mechanism of action different from common antibiotics. This might be important in circumventing existing resistance mechanisms. Here we report about the antibacterial activity in an extended structure-activity relationship study. (c) 2007 Elsevier Masson SAS. All rights reserved.