(-)-(R)-2-bromoapocodeine N-oxide hydrochloride | 1068135-35-2

• 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)-2-bromoapocodeine N-oxide hydrochloride
• 英文别名: (6aR)-2-bromo-10-methoxy-6-methyl-6-oxido-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-11-ol;hydrochloride
• CAS: 1068135-35-2
• 化学式: C₁₈H₁₈BrNO₃*ClH
• 分子量: 412.711
• InChiKey: RHJBACXGOUAVQD-VQISVFHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(R)-2-bromoapocodeine N-oxide hydrochloride 在 ferrous(II) sulfate heptahydrate 、 乙二胺四乙酸 、 氨 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以554 mg的产率得到(-)-(R)-2-bromonorapocodeine
  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
• 作为产物：
  描述：

  2-bromoapocodeine 在 sodium tungstate 、 双氧水 、 盐酸 作用下， 以 1,4-二氧六环 、 水 、 乙醇 、 正戊烷 为溶剂， 生成 (-)-(R)-2-bromoapocodeine N-oxide 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

• Synthesis of Pharmacologically Active Apomorphines by Direct N-Substitution on the Aporphine Backbone
  作者：Attila Sipos、Sándor Berényi

  DOI：10.1055/s-2008-1078494

  日期：——

  A method has been developed for the direct N-substitution of aporphines comprising the N-oxidation-N-deprotection-N-alkylation sequence. This methodology was found to be insensitive to the change in the substitution pattern of rings A or D, therefore it is presumed to be applicable also for aporphines derived from total synthesis and natural sources.

  已经开发了一种用于直接 N-取代阿朴啡的方法，包括 N-氧化-N-脱保护-N-烷基化序列。发现该方法对环 A 或 D 的取代模式的变化不敏感，因此推测它也适用于全合成和天然来源的阿朴啡。