N-propyl-2-phenylnorapomorphine hydrochloride | 1114452-67-3

• 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: N-propyl-2-phenylnorapomorphine hydrochloride
• 英文别名: (6aR)-2-phenyl-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol;hydrochloride
• CAS: 1114452-67-3
• 化学式: C₂₅H₂₅NO₂*ClH
• 分子量: 407.94
• InChiKey: KUBBPURRDHRXFJ-ZMBIFBSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  43.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-propyl-2-phenylnorapocodeine 在 甲烷磺酸 、 DL-蛋氨酸 、 氨 、 盐酸 作用下， 以 水 、 乙醇 为溶剂， 反应 2.0h， 以85%的产率得到N-propyl-2-phenylnorapomorphine hydrochloride
  参考文献：
  名称：

  N-Substituted-2-alkyl- and 2-arylnorapomorphines: Novel, highly active D2 agonists

  摘要：

  Two synthesis routes have been elaborated for the preparation of novel N-substituted-2-alkyl- and 2-arylnorapomorphines. The first one utilizes the traditional methodology of N-substitution of morphinans before acid-catalyzed rearrangements into aporphinoids, while our new approach involves the N-substitution directly on the aporphine backbone. The aimed compounds were obtained in similar overall yields in different synthesis routes and were investigated with respect to their binding affinities and activities to dopamine D-2 and D-1 receptors. These studies revealed remarkable affinity and selectivity of some compounds for D-2 over D-1 receptor subtypes. Partial or full agonist properties were confirmed for all tested compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.047

文献信息

• N-Substituted-2-alkyl- and 2-arylnorapomorphines: Novel, highly active D2 agonists
  作者：Laura Herm、Sándor Berényi、Argo Vonk、Ago Rinken、Attila Sipos

  DOI：10.1016/j.bmc.2009.04.047

  日期：2009.7

  Two synthesis routes have been elaborated for the preparation of novel N-substituted-2-alkyl- and 2-arylnorapomorphines. The first one utilizes the traditional methodology of N-substitution of morphinans before acid-catalyzed rearrangements into aporphinoids, while our new approach involves the N-substitution directly on the aporphine backbone. The aimed compounds were obtained in similar overall yields in different synthesis routes and were investigated with respect to their binding affinities and activities to dopamine D-2 and D-1 receptors. These studies revealed remarkable affinity and selectivity of some compounds for D-2 over D-1 receptor subtypes. Partial or full agonist properties were confirmed for all tested compounds. (C) 2009 Elsevier Ltd. All rights reserved.