mono(N-((4R,4aR,7aR,12bS,E)-3-(cyclopropylmethyl)-9-hydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-ylidene)-2-hydroxy-N-methylethan-1-aminium) monohydrogen monobenzoate | 107819-67-0

• 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: mono(N-((4R,4aR,7aR,12bS,E)-3-(cyclopropylmethyl)-9-hydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-ylidene)-2-hydroxy-N-methylethan-1-aminium) monohydrogen monobenzoate
• CAS: 107819-67-0
• 化学式: 2C₇H₅O₂*C₂₃H₃₁N₂O₃*H
• 分子量: 626.75
• InChiKey: CUFJPFZBUTUUFB-AUZSPYABSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  37.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  96.07
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  mono(N-((4R,4aR,7aR,12bS,E)-3-(cyclopropylmethyl)-9-hydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-ylidene)-2-hydroxy-N-methylethan-1-aminium) monohydrogen monobenzoate 在 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 17-(cyclopropylmethyl)-4,5α-epoxy-6β-morphinan-3-ol
  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
• 作为产物：
  描述：

  N-甲基-2-羟基乙胺 、 17-(cyclopropylmethyl)-4,5α-epoxy-6-oxo-morphinan 、 苯甲酸 以 苯 为溶剂， 反应 18.0h， 生成 mono(N-((4R,4aR,7aR,12bS,E)-3-(cyclopropylmethyl)-9-hydroxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-ylidene)-2-hydroxy-N-methylethan-1-aminium) monohydrogen monobenzoate
  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