3,5-bis(trifluoromethyl)benzyl 3-(1H-indol-3-yl)-2-(5-oxo-5-((1-phenethylpiperidin-4-yl)(phenyl)amino)pentanamido)propanoate | 1338727-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,5-bis(trifluoromethyl)benzyl 3-(1H-indol-3-yl)-2-(5-oxo-5-((1-phenethylpiperidin-4-yl)(phenyl)amino)pentanamido)propanoate
• 英文别名: [3,5-bis(trifluoromethyl)phenyl]methyl (2S)-3-(1H-indol-3-yl)-2-[[5-oxo-5-(N-[1-(2-phenylethyl)piperidin-4-yl]anilino)pentanoyl]amino]propanoate
• CAS: 1338727-41-5
• 化学式: C₄₄H₄₄F₆N₄O₄
• 分子量: 806.848
• InChiKey: FSXQTMXCXNMEIZ-KDXMTYKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  94.7
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  N-苯基-1-(2-苯乙基)-4-哌啶胺 在 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.25h， 生成 3,5-bis(trifluoromethyl)benzyl 3-(1H-indol-3-yl)-2-(5-oxo-5-((1-phenethylpiperidin-4-yl)(phenyl)amino)pentanamido)propanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of new opioid agonist and neurokinin-1 antagonist bivalent ligands

  摘要：

  Newly designed bivalent ligands-opioid agonist/NK1-antagonists have been synthesized. The synthesis of new starting materials-carboxy-derivatives of Fentanyl (1a-1c) was developed. These products have been transformed to 'isoimidium perchlorates' (2a-c). The new isoimidium perchlorates have been successfully implemented in nucleophilic addition reactions, with L-tryptophan 3,5-bis(trifluoromethyl)benzyl ester to give the target compounds-amides (3a-c). Perchlorates (2a-c) successfully undergo reactions with other nucleophiles such as alcohols, amines or hydrazines. The obtained compound 3b exhibited mu-opioid agonist activity and NK1-antagonist activity and may serve as a useful lead compound for the further design of a new series of opioid agonist/NK1-antagonist compounds. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2011.08.027

文献信息

• Synthesis and biological evaluation of new opioid agonist and neurokinin-1 antagonist bivalent ligands
  作者：Ruben Vardanyan、Vlad K. Kumirov、Gary S. Nichol、Peg Davis、Erika Liktor-Busa、David Rankin、Eva Varga、Todd Vanderah、Frank Porreca、Josephine Lai、Victor J. Hruby

  DOI：10.1016/j.bmc.2011.08.027

  日期：2011.10

  Newly designed bivalent ligands-opioid agonist/NK1-antagonists have been synthesized. The synthesis of new starting materials-carboxy-derivatives of Fentanyl (1a-1c) was developed. These products have been transformed to 'isoimidium perchlorates' (2a-c). The new isoimidium perchlorates have been successfully implemented in nucleophilic addition reactions, with L-tryptophan 3,5-bis(trifluoromethyl)benzyl ester to give the target compounds-amides (3a-c). Perchlorates (2a-c) successfully undergo reactions with other nucleophiles such as alcohols, amines or hydrazines. The obtained compound 3b exhibited mu-opioid agonist activity and NK1-antagonist activity and may serve as a useful lead compound for the further design of a new series of opioid agonist/NK1-antagonist compounds. Published by Elsevier Ltd.