N^6α-acetyl-α-oxymorphamine | 109745-13-3

• 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^6α-acetyl-α-oxymorphamine
• 英文别名: N-[(4R,4aS,7S,7aR,12bS)-4a,9-dihydroxy-3-methyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl]acetamide
• CAS: 109745-13-3
• 化学式: C₁₉H₂₄N₂O₄
• 分子量: 344.411
• InChiKey: WZKKHNQPRSDJFT-YIBUMMLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  82
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酸酐 、 6α-oxymorphamine 以 丙酮 为溶剂， 反应 0.5h， 生成 N^6α-acetyl-α-oxymorphamine
  参考文献：
  名称：

  Hybrid bivalent ligands with opiate and enkephalin pharmacophores

  摘要：

  Bivalent ligands consisting of oxymorphamine and [D-Glu2]enkephalin pharmacophores linked through a spacer attached to the 6-amino group of the former and D-Glu of the latter were synthesized in an effort to investigate the possible coexistence of mu and delta recognition sites in the same opioid receptor complex. Of the two bivalent ligands (1,2) synthesized, only 1 had substantially greater antinociceptive potency in mice than its monovalent analogues (1a, 1b). Testing of 1, 1a, and 1b in the guinea pig ileum preparation (GPI) revealed a potency profile similar to that found in vivo, whereas no correlation was observed in the mouse vas deferens (MVD). Binding data indicated the same rank-order affinities at delta receptors as the opioid activities in the GPI and in mice. However, mu binding exhibited no relationship with activity. These results are consistent with the simultaneous occupation of mu and delta by a single bivalent ligand 1, but they are also in harmony with the interaction of 1 with an opioid receptor and an accessory binding site.

  DOI：

  10.1021/jm00394a010

文献信息

• Hybrid bivalent ligands with opiate and enkephalin pharmacophores
  作者：Philip S. Portoghese、D. L. Larson、G. Ronsisvalle、P. W. Schiller、Nguyen Thi Mai Dung、C. Lemieux、A. E. Takemori

  DOI：10.1021/jm00394a010

  日期：1987.11

  Bivalent ligands consisting of oxymorphamine and [D-Glu2]enkephalin pharmacophores linked through a spacer attached to the 6-amino group of the former and D-Glu of the latter were synthesized in an effort to investigate the possible coexistence of mu and delta recognition sites in the same opioid receptor complex. Of the two bivalent ligands (1,2) synthesized, only 1 had substantially greater antinociceptive potency in mice than its monovalent analogues (1a, 1b). Testing of 1, 1a, and 1b in the guinea pig ileum preparation (GPI) revealed a potency profile similar to that found in vivo, whereas no correlation was observed in the mouse vas deferens (MVD). Binding data indicated the same rank-order affinities at delta receptors as the opioid activities in the GPI and in mice. However, mu binding exhibited no relationship with activity. These results are consistent with the simultaneous occupation of mu and delta by a single bivalent ligand 1, but they are also in harmony with the interaction of 1 with an opioid receptor and an accessory binding site.