14β-(3-phenyl-propylamino)morphindole

• 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: 14β-(3-phenyl-propylamino)morphindole
• 英文别名: (1R,2S,13R,21R)-22-methyl-2-(3-phenylpropylamino)-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)-heptaen-16-ol
• 化学式: C₃₂H₃₃N₃O₂
• 分子量: 491.633
• InChiKey: YTWJWDDYBVMLGJ-SSHYCOHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  60.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-碘-3-苯基丙烷 在 六甲基磷酰三胺 、 丙烷-1-硫醇 、 sodium hydride 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 20.0h， 生成 14β-(3-phenyl-propylamino)morphindole
  参考文献：
  名称：

  14-Amino, 14-Alkylamino, and 14-Acylamino Analogs of Oxymorphindole. Differential Effects on Opioid Receptor Binding and Functional Profiles

  摘要：

  The 14-amino analogue of oxymorphindole (OMI) was synthesized and found to possess delta-opioid binding affinity and selectivity similar to OMI. Substitution of the amino group with alkyl, arylalkyl, and acyl groups had relatively little effect on delta-affinity but delta-selectivity was reduced. In functional assays the 14-phenylacetylamino derivative 6d was a selective delta-agonist whereas the phenethylamino analogue 5d was a mu-agonist and low efficacy delta partial agonist that warrants further investigation as an analgesic with low tolerance and dependence.

  DOI：

  10.1021/jm021073r

文献信息

• 14-Amino, 14-Alkylamino, and 14-Acylamino Analogs of Oxymorphindole. Differential Effects on Opioid Receptor Binding and Functional Profiles
  作者：Peter Grundt、Andrew R. Jales、John R. Traynor、John W. Lewis、Stephen M. Husbands

  DOI：10.1021/jm021073r

  日期：2003.4.1

  The 14-amino analogue of oxymorphindole (OMI) was synthesized and found to possess delta-opioid binding affinity and selectivity similar to OMI. Substitution of the amino group with alkyl, arylalkyl, and acyl groups had relatively little effect on delta-affinity but delta-selectivity was reduced. In functional assays the 14-phenylacetylamino derivative 6d was a selective delta-agonist whereas the phenethylamino analogue 5d was a mu-agonist and low efficacy delta partial agonist that warrants further investigation as an analgesic with low tolerance and dependence.