6β-amino-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan | 107819-72-7

• 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: 6β-amino-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan
• CAS: 107819-72-7
• 化学式: C₂₇H₃₂N₂O₄S
• 分子量: 480.628
• InChiKey: IYPIQLSUTIWFNA-JBUKQTOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  81.86
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6β-amino-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan 在 氢氧化钾 作用下， 反应 2.0h， 以61%的产率得到6β-amino-17-(cyclopropylmethyl)-4,5α-epoxymorphinan-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