17-(cyclopropylmethyl)-4,5α-epoxy-6β-morphinan-3-ol hydrochloride | 107846-39-9

• 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: 17-(cyclopropylmethyl)-4,5α-epoxy-6β-morphinan-3-ol hydrochloride
• CAS: 107846-39-9
• 化学式: C₂₃H₃₂N₂O₃*ClH
• 分子量: 420.98
• InChiKey: RGUDGHVZVXHQDK-TXUWJKIMSA-N

反应信息

• 作为反应物：
  描述：

  17-(cyclopropylmethyl)-4,5α-epoxy-6β-morphinan-3-ol hydrochloride 在 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以100%的产率得到6β--17-(cyclopropylmethyl)-4,5α-epoxymorphinan-3-ol dihydrochloride
  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