N-{[(2S,6S,11R)-8-hydroxy-3,6,11-trimethyl-3,4,5,6-tetrahydro-2,6-methano-3-benzazocin-2(1H)-yl]carbonyl}glycylglycyl-L-phenylalanyl-L-methioninamide | 83380-08-9

• 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: N-{[(2S,6S,11R)-8-hydroxy-3,6,11-trimethyl-3,4,5,6-tetrahydro-2,6-methano-3-benzazocin-2(1H)-yl]carbonyl}glycylglycyl-L-phenylalanyl-L-methioninamide
• 英文别名: (-)-(2R,6R,11R)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-2-yl)carbonyl>glycylglycylphenylalanylmethioninamide；(-)-(2R,6R,11R)-[(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-2-yl)carbonyl]glycylglycylphenylalanylmethioninamide
• CAS: 83380-08-9；83435-04-5
• 化学式: C₃₄H₄₆N₆O₆S
• 分子量: 666.842
• InChiKey: WFZKBMKXXAOYTC-BUHASIMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  182.96
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  甘氨酰苯基丙氨酸 在 N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.58h， 生成 N-{[(2S,6S,11R)-8-hydroxy-3,6,11-trimethyl-3,4,5,6-tetrahydro-2,6-methano-3-benzazocin-2(1H)-yl]carbonyl}glycylglycyl-L-phenylalanyl-L-methioninamide
  参考文献：
  名称：

  Synthesis and biological evaluation of a metazocine-containing enkephalinamide. Evidence for nonidentical roles of the tyramine moiety in opiates and opioid peptides

  摘要：

  In an effort to test the hypothesis that the tyramine moiety present in opiates and in opioid peptides plays an identical functional role at opioid receptors, a hybrid enkephalinamide (3) that contains (-)-metazocine (4a) in place of Tyr was synthesized. It was found that 3 and its congeners are inactive or feebly active in the electrically stimulated guinea pig ileum and mouse vas deferens preparations. The results of these studies suggest that the tyramine moiety in opiates and related structures does not play the same functional role as that in the opioid peptides. It is suggested that the different functional roles of the tyramine moiety in opiates and opioid peptides is a consequence of different modes of interaction with common receptors.

  DOI：

  10.1021/jm00354a006