4-(5-(3-formyl-1H-indol-1-yl)pentyloxy)benzonitrile

• 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: 4-(5-(3-formyl-1H-indol-1-yl)pentyloxy)benzonitrile
• 英文别名: 1-(p-cyanophenoxypentyl)indole-3-carbaldehyde；4-[5-(3-Formylindol-1-yl)pentoxy]benzonitrile
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: MGWKKSVBYCEUIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,5-二溴戊烷 在 四丁基溴化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 1.5h， 生成 4-(5-(3-formyl-1H-indol-1-yl)pentyloxy)benzonitrile
  参考文献：
  名称：

  gem -Dithioacetylated indole derivatives as novel antileishmanial agents

  摘要：

  In this communication we report a serendipitously discovered hybrid molecule 1, combining fragment of 3 (an in vivo active antileishmanial molecule) with H2S donor moiety (known for bimodal behavior of cytoprotection and apoptosis), as antileishmanial agent. Compound 1 suppresses 99.82% parasitemia of L donovani infected macrophages at 12.5 mu g/ml without even deforming them (CC50 > 100 mu g/ml). This compound appears cytotoxic for intracellular amastigotes while cytoprotective to host macrophages. The concept can be utilized to develop high therapeutic index NCE (New Chemical Entities) for other macrophage mediated diseases like tuberculosis and cancer. (c) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.09.018

文献信息

• A multicomponent reaction efficiently producing arylmethylene 2-thiohydantoins
  作者：Sharad Porwal、Rishi Kumar、Prakas R. Maulik、Prem M.S. Chauhan

  DOI：10.1016/j.tetlet.2006.06.076

  日期：2006.8

  We describe here a multicomponent reaction that converts aryl/heteroaryl aldehydes efficiently into arylmethylene 2-thiohydantoins. 3-Formylindole behaves exceptionally giving a gem-diacetylthio derivative. A mechanistic study of the behaviour of 3-formylindole, which provides a new class of indole derivative, is described. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• gem -Dithioacetylated indole derivatives as novel antileishmanial agents
  作者：Sharad Porwal、Suman Gupta、Prem M.S. Chauhan

  DOI：10.1016/j.bmcl.2017.09.018

  日期：2017.10

  In this communication we report a serendipitously discovered hybrid molecule 1, combining fragment of 3 (an in vivo active antileishmanial molecule) with H2S donor moiety (known for bimodal behavior of cytoprotection and apoptosis), as antileishmanial agent. Compound 1 suppresses 99.82% parasitemia of L donovani infected macrophages at 12.5 mu g/ml without even deforming them (CC50 > 100 mu g/ml). This compound appears cytotoxic for intracellular amastigotes while cytoprotective to host macrophages. The concept can be utilized to develop high therapeutic index NCE (New Chemical Entities) for other macrophage mediated diseases like tuberculosis and cancer. (c) 2017 Elsevier Ltd. All rights reserved.