6β-azido-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan | 107819-71-6

• 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-azido-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan
• CAS: 107819-71-6
• 化学式: C₂₇H₃₀N₄O₄S
• 分子量: 506.626
• InChiKey: BHFMXRDSMAIPSM-JBUKQTOJSA-N

反应信息

• 作为反应物：
  描述：

  6β-azido-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 48.0h， 以99.6%的产率得到6β-amino-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan 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
• 作为产物：
  描述：

  17-(cyclopropylmethyl)-4,5α-epoxy-3,6α-bis(tosyloxy)morphinan 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以69%的产率得到6β-azido-17-(cyclopropylmethyl)-4,5α-epoxy-3-(tosyloxy)morphinan
  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