4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one-7-spiro-2'-indan

• 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: 4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one-7-spiro-2'-indan
• 英文别名: (4'R,4'aR,7'aR,12'bS)-9'-hydroxy-3'-methylspiro[1,3-dihydroindene-2,6'-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline]-7'-one
• 化学式: C₂₅H₂₅NO₃
• 分子量: 387.478
• InChiKey: RTJUCZCOZIOVDY-PJCFOSJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二氢可待因酮 在 盐酸 、 六甲基磷酰三胺 、 12-冠醚-4 、 三溴化硼 、 lithium hexamethyldisilazane 作用下， 反应 15.08h， 生成 4,5α-epoxy-3-hydroxy-17-methylmorphinan-6-one-7-spiro-2'-indan
  参考文献：
  名称：

  14-Desoxy Analogues of Naltrindole and 7-Spiroindanyloxymorphone:  The Role of the 14-Hydroxy Group at δ Opioid Receptors

  摘要：

  The 14-hydroxy group is known to increase the antagonist potency of mu-selective opioid ligands. To investigate the role of this group at the delta opioid receptor, the 14-desoxy analogues (7 and 9) of the delta-selective ligands, naltrindole (1, NTI) and spiroindanyloxymorphone (2, SIOM), have been synthesized and tested. The in vitro pharmacologic activities of 7 and 9 suggest that the 14-hydroxy group plays an important role in determining the delta selectivity and potency of NTI and SIOM.

  DOI：

  10.1021/jm980209b

文献信息

• 14-Desoxy Analogues of Naltrindole and 7-Spiroindanyloxymorphone:  The Role of the 14-Hydroxy Group at δ Opioid Receptors
  作者：Tushar A. Kshirsagar、Xinqin Fang、Philip S. Portoghese

  DOI：10.1021/jm980209b

  日期：1998.7.1

  The 14-hydroxy group is known to increase the antagonist potency of mu-selective opioid ligands. To investigate the role of this group at the delta opioid receptor, the 14-desoxy analogues (7 and 9) of the delta-selective ligands, naltrindole (1, NTI) and spiroindanyloxymorphone (2, SIOM), have been synthesized and tested. The in vitro pharmacologic activities of 7 and 9 suggest that the 14-hydroxy group plays an important role in determining the delta selectivity and potency of NTI and SIOM.