(E)-4-<<17-(cyclopropylmethyl)-4,5α-epoxy-3-hydroxymorphinan-6β-yl>amino>-4-oxo-2-butenoic acid methyl ester | 107819-66-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: (E)-4-<<17-(cyclopropylmethyl)-4,5α-epoxy-3-hydroxymorphinan-6β-yl>amino>-4-oxo-2-butenoic acid methyl ester
• CAS: 107819-66-9
• 化学式: C₂₅H₃₀N₂O₅
• 分子量: 438.524
• InChiKey: ZHBOGKMSNKELPI-FOOSHTOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  88.1
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  6β-amino-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan 在 氢氧化钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 50.0h， 生成 (E)-4-<<17-(cyclopropylmethyl)-4,5α-epoxy-3-hydroxymorphinan-6β-yl>amino>-4-oxo-2-butenoic acid methyl ester
  参考文献：
  名称：

  Nonequilibrium opioid antagonist activity of 6,14-dideoxynaltrexone derivatives

  摘要：

  A series of 6,14-dideoxynaltrexones that contain different electrophiles in the 6-position were synthesized and evaluated for nonequilibrium opioid antagonist activity in the guinea pig ileum and mouse vas deferens preparations. Members 3-5 of the series possessed irreversible antagonist activity profiles similar to those previously reported for the 14-hydroxy analogues. In contrast, the 14-deoxy-beta-funaltrexamine (14-deoxy-beta-FNA) analogue (6) exhibited a profile of irreversible antagonist activity that differed from that of beta-FNA. It was concluded that the 14-hydroxy group is not essential for irreversible blockage when the electrophile is capable of reacting with a broad spectrum of nucleophiles. However, with a highly selective electrophile such as the fumarate group, the 14-hydroxy function appears to play a role in aligning the molecule to optimize attack by a receptor-based nucleophile.

  DOI：

  10.1021/jm00389a014