phenethyl (E)-4-<<(5α,6β)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl>amino>-4-oxo-2-butenoate | 104035-10-1

• 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: phenethyl (E)-4-<<(5α,6β)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl>amino>-4-oxo-2-butenoate
• CAS: 104035-10-1
• 化学式: C₃₂H₃₆N₂O₆
• 分子量: 544.648
• InChiKey: YXAONQKRSJKQIS-PIVHFSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.33
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  6β-naltrexamine hydrochloride 、 Fumarsaeuremono(2-phenyl)ethylesterchlorid 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 以45%的产率得到phenethyl (E)-4-<<(5α,6β)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl>amino>-4-oxo-2-butenoate
  参考文献：
  名称：

  Irreversible blockage of opioid receptor types by ester homologs of .beta.-funaltrexamine

  摘要：

  A series of ester homologues 2-5 of the mu receptor nonequilibrium antagonist beta-funaltrexamine (1, beta-FNA) was synthesized. These ligands were of interest in our investigation of the relationship between the structure of the ester function and the ability to irreversibly block mu opioid receptors. While all of the ligands were potent reversible agonists in the guinea pig ileum (GPI) and mouse vas deferens (MVD) preparations, most appeared to behave as irreversible antagonists of morphine. The benzyl 5 and phenethyl 6 esters possessed irreversible mu antagonist potency that was of similar magnitude to that of beta-FNA in the GPI. In the MVD, all esters appeared to irreversibly block the agonist effect of morphine, but none of the compounds irreversibly antagonized [D-Ala2,D-Leu5]enkephalin to a significant degree. [3H]Dihydromorphine displacement studies revealed no relationship between the affinity of the esters 1-6 and the irreversible blockage of mu receptors in the GPI or MVD. Possible reasons for the observed structure-activity relationship are discussed.

  DOI：

  10.1021/jm00160a013