1-(5-氯戊基)-5-硝基吲哚 | 61205-62-7

• 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
• 中文名称: 1-(5-氯戊基)-5-硝基吲哚
• 英文名称: 1-(5-chloropentyl)-5-nitro-1H-indole
• 英文别名: 1-(5-Chlorpentyl)-5-nitroindol；1-(5-chloropentyl)-5-nitroindole
• CAS: 61205-62-7
• 化学式: C₁₃H₁₅ClN₂O₂
• 分子量: 266.727
• InChiKey: BJLJRSHWQTWAEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-氯戊基)-5-硝基吲哚 、 三苯基膦 在 potassium iodide 作用下， 以 乙腈 为溶剂， 以21%的产率得到(5-(5-nitro-1H-indol-1-yl)pentyl) triphenylphosphonium iodide
  参考文献：
  名称：

  Indolylalkyltriphenylphosphonium Analogues Are Membrane-Depolarizing Mycobactericidal Agents

  摘要：

  Agents that selectively target the mycobacterial membrane could potentially shorten treatment time for tuberculosis, reduce relapse, and curtail emergence of resistant strains. The lipophilicity and extensive charge-delocalized state of the triphenylphosphonium cation strongly favor accumulation within bacterial membranes. Here, we explored the antimycobacterial activities and membrane-targeting properties of indolylalkyltriphenylphosphonium analogues. The most active analogues preferentially inhibited growth of Mycobacterium tuberculosis H37Rv (MIC50 2-4 mu M) and were bactericidal against Mycobacterium bovis BCG (MBC99 3 mu M). In spite of their propensity to accumulate within membranes, we found no evidence that these compounds permeabilized mycobacterial membranes or induced cell-envelope stress. Our investigations indicated that their bacterical effects stem from sustained depolarization of mycobacterial membranes and ensuing disruptive effects on electron transfer and cell division.

  DOI：

  10.1021/acsmedchemlett.7b00287
• 作为产物：
  描述：

  3-chloro-4-(5-nitro-2-piperidin-1-ylphenyl)-1-phenylazetidin-2-one 以30%的产率得到
  参考文献：
  名称：

  BENTLEY R. L.; SUSCHITZKY H., J. CHEM. SOC. PERKIN TRANS., 1976, PART 1, NO 16, 1725-1734

  摘要：

  DOI：

文献信息

• Indolylalkyltriphenylphosphonium Analogues Are Membrane-Depolarizing Mycobactericidal Agents
  作者：Ming Li、Samuel A. Nyantakyi、Pooja Gopal、Dinah binte Aziz、Thomas Dick、Mei-Lin Go

  DOI：10.1021/acsmedchemlett.7b00287

  日期：2017.11.9

  Agents that selectively target the mycobacterial membrane could potentially shorten treatment time for tuberculosis, reduce relapse, and curtail emergence of resistant strains. The lipophilicity and extensive charge-delocalized state of the triphenylphosphonium cation strongly favor accumulation within bacterial membranes. Here, we explored the antimycobacterial activities and membrane-targeting properties of indolylalkyltriphenylphosphonium analogues. The most active analogues preferentially inhibited growth of Mycobacterium tuberculosis H37Rv (MIC50 2-4 mu M) and were bactericidal against Mycobacterium bovis BCG (MBC99 3 mu M). In spite of their propensity to accumulate within membranes, we found no evidence that these compounds permeabilized mycobacterial membranes or induced cell-envelope stress. Our investigations indicated that their bacterical effects stem from sustained depolarization of mycobacterial membranes and ensuing disruptive effects on electron transfer and cell division.
• BENTLEY R. L.; SUSCHITZKY H., J. CHEM. SOC. PERKIN TRANS., 1976, PART 1, NO 16, 1725-1734
  作者：BENTLEY R. L.、 SUSCHITZKY H.

  DOI：——

  日期：——