4-oxo-4-[4-(phenylpropionylamino)piperidin-1-yl]butyric acid

• 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: 4-oxo-4-[4-(phenylpropionylamino)piperidin-1-yl]butyric acid
• 英文别名: 4-oxo-4-[4-(N-propanoylanilino)piperidin-1-yl]butanoic acid
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: FHBUESMYRMOUIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-oxo-4-[4-(phenylpropionylamino)piperidin-1-yl]butyric acid 、 Boc-Tyr-D-Ala-Gly-Phe-NH-NH2 在 N-甲基吗啉 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Development of Novel Enkephalin Analogues that Have Enhanced Opioid Activities at Both μ and δ Opioid Receptors

  摘要：

  Enkephalin analogues with a 4-anilidopiperidine scaffold have been designed and synthesized to achieve therapeutic benefit for the treatment of pain due to mixed mu and delta opioid agonist activities. Ligand 16, in which a Dmt-substituted enkephalin-like structure was linked to the N-phenyl-N-piperidin-4-yl propionamide moiety, showed very high binding affinities (0.4 nM) at mu and delta receptors with an increased hydrophobicity (aLogP = 2.96). This novel lead compound was found to have very potent agonist activities in MVD (1.8 nM) and GPI (8.5 nM) assays.

  DOI：

  10.1021/jm061465o
• 作为产物：
  描述：

  丁二酸酐 、 N-苯基-N-(4-哌啶)丙胺 混合盐酸 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 4-oxo-4-[4-(phenylpropionylamino)piperidin-1-yl]butyric acid
  参考文献：
  名称：

  Development of Novel Enkephalin Analogues that Have Enhanced Opioid Activities at Both μ and δ Opioid Receptors

  摘要：

  Enkephalin analogues with a 4-anilidopiperidine scaffold have been designed and synthesized to achieve therapeutic benefit for the treatment of pain due to mixed mu and delta opioid agonist activities. Ligand 16, in which a Dmt-substituted enkephalin-like structure was linked to the N-phenyl-N-piperidin-4-yl propionamide moiety, showed very high binding affinities (0.4 nM) at mu and delta receptors with an increased hydrophobicity (aLogP = 2.96). This novel lead compound was found to have very potent agonist activities in MVD (1.8 nM) and GPI (8.5 nM) assays.

  DOI：

  10.1021/jm061465o

文献信息

• Development of Novel Enkephalin Analogues that Have Enhanced Opioid Activities at Both μ and δ Opioid Receptors
  作者：Yeon Sun Lee、Ravil Petrov、Chad K. Park、Shou-wu Ma、Peg Davis、Josephine Lai、Frank Porreca、Ruben Vardanyan、Victor J. Hruby

  DOI：10.1021/jm061465o

  日期：2007.11.1

  Enkephalin analogues with a 4-anilidopiperidine scaffold have been designed and synthesized to achieve therapeutic benefit for the treatment of pain due to mixed mu and delta opioid agonist activities. Ligand 16, in which a Dmt-substituted enkephalin-like structure was linked to the N-phenyl-N-piperidin-4-yl propionamide moiety, showed very high binding affinities (0.4 nM) at mu and delta receptors with an increased hydrophobicity (aLogP = 2.96). This novel lead compound was found to have very potent agonist activities in MVD (1.8 nM) and GPI (8.5 nM) assays.