4-[5-[3-[(Z)-(5-oxo-2-sulfanylideneimidazolidin-4-ylidene)methyl]indol-1-yl]pentoxy]benzonitrile | 1190367-69-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-[5-[3-[(Z)-(5-oxo-2-sulfanylideneimidazolidin-4-ylidene)methyl]indol-1-yl]pentoxy]benzonitrile
• CAS: 1190367-69-1
• 化学式: C₂₄H₂₂N₄O₂S
• 分子量: 430.53
• InChiKey: FGIKASKTKROYNK-STZFKDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[5-[3-[(Z)-(5-oxo-2-sulfanylideneimidazolidin-4-ylidene)methyl]indol-1-yl]pentoxy]benzonitrile 在 叔丁基过氧化氢 、 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以74%的产率得到4-[5-[3-[(Z)-(2-amino-5-oxo-1H-imidazol-4-ylidene)methyl]indol-1-yl]pentoxy]benzonitrile
  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
• 作为产物：
  描述：

  4-(5-(3-formyl-1H-indol-1-yl)pentyloxy)benzonitrile 、 2-硫代乙内酰脲 在 C.I.酸性橙108 作用下， 以 乙醇 为溶剂， 以82%的产率得到4-[5-[3-[(Z)-(5-oxo-2-sulfanylideneimidazolidin-4-ylidene)methyl]indol-1-yl]pentoxy]benzonitrile
  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.