3,8-dibromoglaucine | 121387-31-3

• 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: 3,8-dibromoglaucine
• CAS: 121387-31-3
• 化学式: C₂₁H₂₃Br₂NO₄
• 分子量: 513.226
• InChiKey: ASBWDKCWWYXICI-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.16
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  海罂粟碱 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 作用下， 反应 2.0h， 以47%的产率得到3,8-dibromoglaucine
  参考文献：
  名称：

  Structure–affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity

  摘要：

  Halogenation of the aporphine alkaloid boldine at the 3-position leads to increased affinity for rat brain D-1-like dopaminergic receptors with some selectivity over D-2-like receptors. A series of 3-halogenated and 3,8-dihalogenated (halogen = Cl, Br or 1) derivatives of predicentrine (9-O-methylboldine) and glaucine (2,9-di-O-methylboldine) were prepared and assayed for binding at D-1 and D-2 sites. Halogenation of predicentrine led to strong increases in affinity for D-1-like receptors, while the affinities for D-2-like receptors were either practically unchanged or reduced three- to fourfold. Halogenated glaucine derivatives did not show any clear trend towards enhanced selectivity, and the affinities were poor and similar to or worse than the values previously recorded for glaucine itself. Together with earlier work on boldine derivatives, these results suggest that the 2-hydroxy group on the aporphine skeleton may determine a binding mode favoring D-1-like over D-2-like receptors, with enhanced affinity when the C-3 position is halogenated. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.022

文献信息

• Bhakuni, Dewan S.; Jain, Sudha; Singh, Meenakshi, Heterocycles, 1989, vol. 28, # 1, p. 315 - 320
  作者：Bhakuni, Dewan S.、Jain, Sudha、Singh, Meenakshi

  DOI：——

  日期：——