3-bromopredicentrine | 87167-04-2

• 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: 3-bromopredicentrine
• 英文别名: (S)-3-bromo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol；(6aS)-3-bromo-1,9,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-2-ol
• CAS: 87167-04-2
• 化学式: C₂₀H₂₂BrNO₄
• 分子量: 420.303
• InChiKey: OVHSYOZHNXMGQC-ZDUSSCGKSA-N

物化性质

• 熔点：
  192-193 °C (decomp)
• 沸点：
  509.0±50.0 °C(predicted)
• 密度：
  1.422±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromopredicentrine 在 正丁基锂 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.17h， 生成 3-carboxipredicentrine hydrochloride
  参考文献：
  名称：

  Towards a more selective analogue of oxaliplatin: Synthesis of [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)]

  摘要：

  A novel oxaliplatin analogue, [Pt((1R,2R)-diaminocyclohexane)(3-carboxypredicentrinato)], boldiplatin, has been synthesized by the coordination of the boldine derivative 3-carboxypredicentrinate to the corresponding platinum(II) moiety in 5.8% overall yield. The complex was fully characterized and biologically evaluated in vitro. Boldiplatin was compared with its parent drug oxaliplatin, showing equal activity over four human tumor cell lines (MCF-7, MDA-MB-231, PC-3 and HT-29) and a tenfold decrease in toxicity over a non-tumor cell line (DHF). This selectivity makes boldiplatin a good candidate for further evaluations to assess its potential as antitumor drug. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.12.013
• 作为产物：
  描述：

  海罂粟碱 在 sodium tetrahydroborate 、 硫酸 、 氢溴酸 、 双氧水 作用下， 反应 80.0h， 生成 3-bromopredicentrine
  参考文献：
  名称：

  Synthesis and properties of glaucine-quinol

  摘要：

  DOI：

  10.1016/s0040-4020(01)88694-4

文献信息

• Structure–affinity relationships of halogenated predicentrine and glaucine derivatives at D1 and D2 dopaminergic receptors: halogenation and D1 receptor selectivity
  作者：Marcelo Asencio、Claudio Hurtado-Guzmán、John J. López、Bruce K. Cassels、Philippe Protais、Abdeslam Chagraoui

  DOI：10.1016/j.bmc.2005.03.022

  日期：2005.6

  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.