(5Z)-5-[[1-[5-(4-phenylpiperazin-1-yl)pentyl]indol-3-yl]methylidene]-2-sulfanylideneimidazolidin-4-one | 1190367-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (5Z)-5-[[1-[5-(4-phenylpiperazin-1-yl)pentyl]indol-3-yl]methylidene]-2-sulfanylideneimidazolidin-4-one
• CAS: 1190367-71-5
• 化学式: C₂₇H₃₁N₅OS
• 分子量: 473.642
• InChiKey: VNTAYOALAPMBDG-CLCOLTQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  84.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-硫代乙内酰脲 、 1-[5-(4-Phenylpiperazin-1-yl)pentyl]indole-3-carbaldehyde 在 C.I.酸性橙108 作用下， 以 乙醇 为溶剂， 以69%的产率得到(5Z)-5-[[1-[5-(4-phenylpiperazin-1-yl)pentyl]indol-3-yl]methylidene]-2-sulfanylideneimidazolidin-4-one
  参考文献：
  名称：

  Discovery of Novel Antileishmanial Agents in an Attempt to Synthesize Pentamidine−Aplysinopsin Hybrid Molecule

  摘要：

  In an attempt to synthesize pent amidine - aplysinopsin hybrid molecule 25, a lead molecule 8 (containing Z-configured aplysinopsin moiety) was identified for antileishmanial activity. Optimization of lead 8 provided 24 (containing E-configured aplysinopsin) possessing 10 times more activity and 401-fold less toxicity than the drug pentamidine in cell based assays. Synthesis of 24 was possible, surprisingly, because of two innate reactivities of indole-3-carbaldehyde which provided it in diastereoand regio-selectively pure form without recourse to the long reaction pathway.

  DOI：

  10.1021/jm900564x

文献信息

• Discovery of Novel Antileishmanial Agents in an Attempt to Synthesize Pentamidine−Aplysinopsin Hybrid Molecule
  作者：Sharad Porwal、Shikha S. Chauhan、Prem M. S. Chauhan、Nishi Shakya、Aditya Verma、Suman Gupta

  DOI：10.1021/jm900564x

  日期：2009.10.8

  In an attempt to synthesize pent amidine - aplysinopsin hybrid molecule 25, a lead molecule 8 (containing Z-configured aplysinopsin moiety) was identified for antileishmanial activity. Optimization of lead 8 provided 24 (containing E-configured aplysinopsin) possessing 10 times more activity and 401-fold less toxicity than the drug pentamidine in cell based assays. Synthesis of 24 was possible, surprisingly, because of two innate reactivities of indole-3-carbaldehyde which provided it in diastereoand regio-selectively pure form without recourse to the long reaction pathway.