(5α,7α)-7-aminomethyl-17-(cyclopropylmethyl)-4,5-epoxy-6-methoxy-6,14-ethanomorphinan-3-ol | 329310-71-6

• 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: (5α,7α)-7-aminomethyl-17-(cyclopropylmethyl)-4,5-epoxy-6-methoxy-6,14-ethanomorphinan-3-ol
• 英文别名: 7α-aminomethyl-N-cyclopropylmethyl-6,14-endoethanotetrahydronororipavine
• CAS: 329310-71-6
• 化学式: C₂₄H₃₂N₂O₃
• 分子量: 396.53
• InChiKey: JEHUXDJQKIEJNE-RXCHFPMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  67.95
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-苯基-2-丙烯酰氯 、 (5α,7α)-7-aminomethyl-17-(cyclopropylmethyl)-4,5-epoxy-6-methoxy-6,14-ethanomorphinan-3-ol 在 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 以71%的产率得到BU 160
  参考文献：
  名称：

  Cinnamoyl Derivatives of 7α-Amino- and 7α-(Aminomethyl)-N-(cyclopropylmethyl)-6,14-endo-ethanotetrahydronororipavines are High-Potency Opioid Antagonists

  摘要：

  DOI：

  10.1002/1522-2675(20001220)83:12<3122::aid-hlca3122>3.0.co;2-2
• 作为产物：
  描述：

  (5α,7α)-17-(cyclopropylmethyl)-4,5-epoxy-3,6-dimethoxy-6,14-ethenomorphinan-7-carboxyl chloride 在 palladium on activated charcoal 氢氧化钾 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二乙二醇 为溶剂， 45.0 ℃ 、206.84 kPa 条件下， 反应 32.0h， 生成 (5α,7α)-7-aminomethyl-17-(cyclopropylmethyl)-4,5-epoxy-6-methoxy-6,14-ethanomorphinan-3-ol
  参考文献：
  名称：

  Cinnamoyl Derivatives of 7α-Amino- and 7α-(Aminomethyl)-N-(cyclopropylmethyl)-6,14-endo-ethanotetrahydronororipavines are High-Potency Opioid Antagonists

  摘要：

  DOI：

  10.1002/1522-2675(20001220)83:12<3122::aid-hlca3122>3.0.co;2-2

文献信息

• Fumaroylamino-4,5-epoxymorphinans and Related Opioids with Irreversible μ Opioid Receptor Antagonist Effects
  作者：Humphrey A. Moynihan、Ian. Derrick、Jillian H. Broadbear、Benjamin M. Greedy、Mario D. Aceto、Louis S. Harris、Lauren C. S. Purington、Mark P. Thomas、James H. Woods、John R. Traynor、Stephen M. Husbands、John W. Lewis

  DOI：10.1021/jm301096s

  日期：2012.11.26

  We have.-previously, shown that cinnamoyl derivatives of 14 beta-amino-17-cyclopropylmethyl-7,8-dihydronormorphinone and 7 alpha-aminomethyl-6,14-endoethanonoror-ipavine have pronounced pseudoirreversible mu opioid receptor.. (MOR) antagonism. the present communication describes the synthesis and evaluation of fumaroylamino analogues of these cinnamoylamino derivatives together with some related. fumaroyl derivatives. The predominant activity of the new ligands was MOR antagonism. The fumaroylamino analogues (2a, 5a) of the pseudoirreversible antagonist cinnamoylamino morphinones and oripavines (2b, 5b) were themselves irreversible antagonists in vivo. However the fumaroylamino derivatives had significantly higher MOR efficacy than the cinnamoylamino derivative's in mouse antinociceptive tests. Comparison Of 2a and 5a with the prototypic fumaroylamino opioid beta-FNA (1a) shows that they have similar MOR irreversible antagonist actions but differ in the nature of their opioid receptor. agonist effects; 2a is a predominant MOR agonist and Sa shows no opioid receptor selectivity, whereas. the agonist effect of beta-FNA is Clearly kappa opioid riceptor (KOR) mediated.