7α-(aminomethyl)-6,14-endo-ethanotetrahydrothebaine | 957053-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 7α-(aminomethyl)-6,14-endo-ethanotetrahydrothebaine
• 英文别名: [(1S,2S,6R,14R,15R,16R)-11,15-dimethoxy-5-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-16-yl]methanamine
• CAS: 957053-57-5
• 化学式: C₂₂H₃₀N₂O₃
• 分子量: 370.492
• InChiKey: KPBTWVGBHUMGCP-GEAUKGQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  57
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7α-(aminomethyl)-6,14-endo-ethanotetrahydrothebaine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以70%的产率得到7α-(aminomethyl)-6,14-endoethanotetrahydrooripavine
  参考文献：
  名称：

  Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endo-ethanotetrahydrooripavine and Related Opioid Ligands

  摘要：

  A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7 alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu. opioid receptor.

  DOI：

  10.1021/jm070255o
• 作为产物：
  描述：

  7α-(Aminomethyl)-6,14-endo-ethenotetrahydrothebaine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、275.8 kPa 条件下， 以61%的产率得到7α-(aminomethyl)-6,14-endo-ethanotetrahydrothebaine
  参考文献：
  名称：

  Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-endo-ethanotetrahydrothebaine and 7α-Aminomethyl-6,14-endo-ethanotetrahydrooripavine and Related Opioid Ligands

  摘要：

  A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7 alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu. opioid receptor.

  DOI：

  10.1021/jm070255o

文献信息

• Cinnamoyl Derivatives of 7α-Aminomethyl-6,14-<i>endo</i>-ethanotetrahydrothebaine and 7α-Aminomethyl-6,14-<i>endo</i>-ethanotetrahydrooripavine and Related Opioid Ligands
  作者：David Rennison、Adrian P. Neal、Gerta Cami-Kobeci、Mario D. Aceto、Fernando Martinez-Bermejo、John W. Lewis、Stephen M. Husbands

  DOI：10.1021/jm070255o

  日期：2007.10.1

  A new series of ligands has been synthesized where the cinnamoyl group of the 14-cinnamoylamino morphinones has been introduced to the 7 alpha-substituent of the 6,14-bridged oripavine series. In vitro the compounds were mostly low efficacy partial agonists or antagonists with some selectivity for the mu opioid receptor, with evidence of mu efficacy in vivo. The similarity in SAR between these 6,14-bridged oripavines and the 14-cinnamoylamino series suggests a similar mode of interaction with the mu. opioid receptor.