17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-methoxy-6,7:2',3'-indolomorphinan | 210967-60-5

• 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)-6,7-didehydro-4,5α-epoxy-3-methoxy-6,7:2',3'-indolomorphinan
• 英文别名: (1S,2R,13R,21R)-22-(cyclopropylmethyl)-16-methoxy-14-oxa-11,22-diazaheptacyclo[13.9.1.01,13.02,21.04,12.05,10.019,25]pentacosa-4(12),5,7,9,15,17,19(25)-heptaene
• CAS: 210967-60-5
• 化学式: C₂₇H₂₈N₂O₂
• 分子量: 412.532
• InChiKey: LGMKVDVJIDZJEF-LQIWJUJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-methoxy-6,7:2',3'-indolomorphinan 在 盐酸 、 三溴化硼 作用下， 生成 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-hydroxy-6,7:2',3'-indolomorphinan
  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
• 作为产物：
  描述：

  二氢可待因酮 在 盐酸 、 氯甲酸乙烯酯 、 碳酸氢钠 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 62.0h， 生成 17-(cyclopropylmethyl)-6,7-didehydro-4,5α-epoxy-3-methoxy-6,7:2',3'-indolomorphinan
  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