4,5α-epoxy-3-methoxy-8-oxomorphinan | 155206-62-5

• 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: 4,5α-epoxy-3-methoxy-8-oxomorphinan
• CAS: 155206-62-5
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: FHMFGSMEIJRXOG-BYLNDYCFSA-N

物化性质

• 沸点：
  475.6±45.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.59
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4,5α-epoxy-3-methoxy-8-oxomorphinan 在 盐酸 、 三溴化硼 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 19.5h， 生成 17-(cyclopropylmethyl)-4,5α-epoxy-3-hydroxy-8-oxomorphinan
  参考文献：
  名称：

  Synthesis and .delta.-Opioid Receptor Antagonist Activity of a Naltrindole Analog with a Regioisomeric Indole Moiety

  摘要：

  Indolomorphinans 2 and 3, in which the indole moiety is fused to the 7,8-position of the morphinan system, have been synthesized from dihydropseudocodeinone 4 and evaluated for antagonist activity on the mouse vas deferens (MVD) and guinea pig ileum (GPI) preparations. Indolomorphinan 2 was found to be similar to 1/60th as potent as naltrindole 1 in the MVD and an agonist in the GPI preparation. A comparable difference in affinity between 1 and 2 was observed. The methyl analogue 3 was inactive in both preparations. The results of this study support the idea that the regio orientation of the indolic benzene moiety of 1 is optimal for delta-opioid receptor antagonist activity. It is proposed that the proper alignment of the benzene moiety with an address subsite on the delta receptor is critical for potent delta antagonist activity.

  DOI：

  10.1021/jm00038a019
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4,5α-epoxy-3-methoxy-8-oxomorphinan
  参考文献：
  名称：

  Synthesis and .delta.-Opioid Receptor Antagonist Activity of a Naltrindole Analog with a Regioisomeric Indole Moiety

  摘要：

  Indolomorphinans 2 and 3, in which the indole moiety is fused to the 7,8-position of the morphinan system, have been synthesized from dihydropseudocodeinone 4 and evaluated for antagonist activity on the mouse vas deferens (MVD) and guinea pig ileum (GPI) preparations. Indolomorphinan 2 was found to be similar to 1/60th as potent as naltrindole 1 in the MVD and an agonist in the GPI preparation. A comparable difference in affinity between 1 and 2 was observed. The methyl analogue 3 was inactive in both preparations. The results of this study support the idea that the regio orientation of the indolic benzene moiety of 1 is optimal for delta-opioid receptor antagonist activity. It is proposed that the proper alignment of the benzene moiety with an address subsite on the delta receptor is critical for potent delta antagonist activity.

  DOI：

  10.1021/jm00038a019