N-cyclopropylmethyl-14β-cinnamoyloxy-7,8-dihydrocodeinone | 1134195-73-5

• 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: N-cyclopropylmethyl-14β-cinnamoyloxy-7,8-dihydrocodeinone
• 英文别名: N-Cyclopropylmethyl-14beta-cinnamoyloxy-7,8-dihydrocodeinone；[(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-9-methoxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl] (E)-3-phenylprop-2-enoate
• CAS: 1134195-73-5
• 化学式: C₃₀H₃₁NO₅
• 分子量: 485.58
• InChiKey: WGDLNMCFJZEUHA-ATTGEPADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  反式-桂皮酸酐 、 纳曲酮EP杂质J 以 甲苯 为溶剂， 以44%的产率得到N-cyclopropylmethyl-14β-cinnamoyloxy-7,8-dihydrocodeinone
  参考文献：
  名称：

  14β-O-Cinnamoylnaltrexone and Related Dihydrocodeinones are Mu Opioid Receptor Partial Agonists with Predominant Antagonist Activity

  摘要：

  14-O-Cinnamoyl esters of naltrexone (6) were synthesized and evaluated in isolated tissue assays in vitro and in vivo in mouse antinociceptive assays. Their predominant opioid receptor activity was mu receptor (MOR) antagonism, but the unsubstituted cinnamoyl derivative (6a) had partial MOR agonist activity in vitro and in vivo. When compared to the equivalent 14-cinnamoylaminomorphinones (5), the cinnamoyloxy morphinones (6) as MOR antagonists had a shorter duration of action and were less effective as pseudoirreversible antagonists. The antinociceptive activity of the cinnamoyloxycodeinones (7) was not significantly greater than that of the morphinones (6), but they exhibited no evidence of any pseudo irreversible MOR antagonism. In both respects, these profiles differed from those of the equivalent 14-cinnamoylaminocodeinones (4).

  DOI：

  10.1021/jm8012272

文献信息

• 14β-<i>O</i>-Cinnamoylnaltrexone and Related Dihydrocodeinones are Mu Opioid Receptor Partial Agonists with Predominant Antagonist Activity
  作者：H. Moynihan、A. R. Jales、B. M. Greedy、D. Rennison、J. H. Broadbear、L. Purington、J. R. Traynor、J. H. Woods、J. W. Lewis、S. M. Husbands

  DOI：10.1021/jm8012272

  日期：2009.3.26

  14-O-Cinnamoyl esters of naltrexone (6) were synthesized and evaluated in isolated tissue assays in vitro and in vivo in mouse antinociceptive assays. Their predominant opioid receptor activity was mu receptor (MOR) antagonism, but the unsubstituted cinnamoyl derivative (6a) had partial MOR agonist activity in vitro and in vivo. When compared to the equivalent 14-cinnamoylaminomorphinones (5), the cinnamoyloxy morphinones (6) as MOR antagonists had a shorter duration of action and were less effective as pseudoirreversible antagonists. The antinociceptive activity of the cinnamoyloxycodeinones (7) was not significantly greater than that of the morphinones (6), but they exhibited no evidence of any pseudo irreversible MOR antagonism. In both respects, these profiles differed from those of the equivalent 14-cinnamoylaminocodeinones (4).