((S)-2-(4-Hydroxy-phenyl)-1-{2-oxo-2-[4-(phenyl-propionyl-amino)-piperidin-1-yl]-ethylcarbamoyl}-ethyl)-carbamic acid benzyl ester | 85221-32-5

• 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: ((S)-2-(4-Hydroxy-phenyl)-1-{2-oxo-2-[4-(phenyl-propionyl-amino)-piperidin-1-yl]-ethylcarbamoyl}-ethyl)-carbamic acid benzyl ester
• CAS: 85221-32-5
• 化学式: C₃₃H₃₈N₄O₆
• 分子量: 586.688
• InChiKey: NTVCKURQSFKGGY-LJAQVGFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  128.28
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  溶剂黄146 、 ((S)-2-(4-Hydroxy-phenyl)-1-{2-oxo-2-[4-(phenyl-propionyl-amino)-piperidin-1-yl]-ethylcarbamoyl}-ethyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以92%的产率得到N-<1-(tyrosylglycyl)-4-piperidyl>-N-phenylpropanamide acetate
  参考文献：
  名称：

  Synthesis and evaluation of 1- and 2-substituted fentanyl analogs for opioid activity

  摘要：

  We synthesized fentanyl analogues that possess key groups common to the opioid peptides to investigate whether or not these two classes of compounds interact with common subsites on opioid receptors. The design of the analogues was based on the possibility of structural analogy between the two aromatic rings of fentanyl and the Tyr1 and Phe4 residues of the opioid peptides. The synthesized compounds showed very weak or no opioid activity as tested in the electrically stimulated longitudinal muscle of the guinea pig ileum or mouse vas deferens preparations. These results, together with those of reported studies, suggest that fentanyl and the opioid peptides interact with different subsites on either mu or sigma receptors. Studies using the irreversible mu opioid receptor antagonist, beta-funaltrexamine, indicate that fentanyl interacts preferentially with mu opioid receptors.

  DOI：

  10.1021/jm00357a007
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 、 N-(1-glycyl-4-piperidyl)-N-phenylpropanamide 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以58%的产率得到((S)-2-(4-Hydroxy-phenyl)-1-{2-oxo-2-[4-(phenyl-propionyl-amino)-piperidin-1-yl]-ethylcarbamoyl}-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and evaluation of 1- and 2-substituted fentanyl analogs for opioid activity

  摘要：

  We synthesized fentanyl analogues that possess key groups common to the opioid peptides to investigate whether or not these two classes of compounds interact with common subsites on opioid receptors. The design of the analogues was based on the possibility of structural analogy between the two aromatic rings of fentanyl and the Tyr1 and Phe4 residues of the opioid peptides. The synthesized compounds showed very weak or no opioid activity as tested in the electrically stimulated longitudinal muscle of the guinea pig ileum or mouse vas deferens preparations. These results, together with those of reported studies, suggest that fentanyl and the opioid peptides interact with different subsites on either mu or sigma receptors. Studies using the irreversible mu opioid receptor antagonist, beta-funaltrexamine, indicate that fentanyl interacts preferentially with mu opioid receptors.

  DOI：

  10.1021/jm00357a007