glycylglycylphenylalanylmethioninamide hydrochloride | 83380-11-4

• 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: glycylglycylphenylalanylmethioninamide hydrochloride
• CAS: 83380-11-4
• 化学式: C₁₈H₂₇N₅O₄S*ClH
• 分子量: 445.97
• InChiKey: UGNVEFYVDYIWJK-IODNYQNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.07
• 重原子数：
  29.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  156.41
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  glycylglycylphenylalanylmethioninamide hydrochloride 、 alkaline earth salt of/the/ methylsulfuric acid 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以40%的产率得到(-)-(2R,6R,11R)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide
  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
• 作为产物：
  描述：

  Boc-Gly-Gly-Phe-Met-OH 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到glycylglycylphenylalanylmethioninamide hydrochloride
  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