(-)-(R)-11-methoxy-10-methylaporphine hydrochloride | 143051-84-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (-)-(R)-11-methoxy-10-methylaporphine hydrochloride
• 英文别名: 10-methyl-11-methoxyaporphine hydrochloride
• CAS: 143051-84-7
• 化学式: C₁₉H₂₁NO*ClH
• 分子量: 315.843
• InChiKey: CDJJMRZUHACNQY-PKLMIRHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-(R)-11-methoxy-10-methylaporphine hydrochloride 在 氢溴酸 作用下， 反应 3.5h， 生成 (-)-(R)-11-hydroxy-10-methylaporphine
  参考文献：
  名称：

  (R)-11-Hydroxy- and (R)-11-Hydroxy-10-methylaporphine: Synthesis, Pharmacology, and Modeling of D2A and 5-HT1A Receptor Interactions

  摘要：

  (R)-11-Hydroxyaporphine (2) and (R)-11-hydroxy-10-methylaporphine (3) were synthesized from natural morphine by using new, short, and efficient synthetic sequences. The dopaminergic and serotonergic effects of 2 and 3 were evaluated by use of in vitro and in vivo test systems. The results indicate that 3 is a potent, selective, and efficacious 6-HT1A receptor agonist. In contrast, 2 is a partial 5-HT1A receptor agonist of low potency which has affinity also for central D-1 and D-2A receptors. The differences in pharmacological profiles were rationalized by modeling of ligand-receptor interactions using homology-based receptor models of the 6-HT1A and D-2A receptor binding site. The selective and pronounced serotonergic effects of 3 appear to be due to the CIO-methyl group, which is accommodated by a lipophilic pocket in the 5-HT1A receptor. In contrast, the C10-methyl group of 3 is not accommodated by the binding site model of the D-2A receptor.

  DOI：

  10.1021/jm00004a011