8-bromo-6-methyl-3-(3,4,5-trimethoxyphenyl)coumarin | 1247212-21-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-bromo-6-methyl-3-(3,4,5-trimethoxyphenyl)coumarin
• 英文别名: 8-Bromo-6-methyl-3-(3'',4'',5''-trimethoxyphenyl)coumarin；8-bromo-6-methyl-3-(3,4,5-trimethoxyphenyl)chromen-2-one
• CAS: 1247212-21-0
• 化学式: C₁₉H₁₇BrO₅
• 分子量: 405.245
• InChiKey: VWKQTQVNQOYLAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴-2-羟基-5-甲基苯甲醛 、 3,4,5-三甲氧基苯乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以50%的产率得到8-bromo-6-methyl-3-(3,4,5-trimethoxyphenyl)coumarin
  参考文献：
  名称：

  New halogenated 3-phenylcoumarins as potent and selective MAO-B inhibitors

  摘要：

  With the aim to find out the structural features for the MAO inhibitory activity and selectivity, in the present communication we report the synthesis and pharmacological evaluation of a new series of bromo-6-methyl-3-phenylcoumarin derivatives (with bromo atom in both different benzene rings of the skeleton) with and without different number of methoxy substituent at the 3-phenyl ring. The methoxy substituents were introduced, in this new scaffold, in the meta and/or para positions of the 3-phenyl ring. The synthesized compounds 3-7 were evaluated as MAO-A and B inhibitors using R-(-)-deprenyl (selegiline) and iproniazide as reference inhibitors, showing, most of them, MAO-B inhibitory activities in the low nanomolar range. Compounds 4 (IC50 = 11.05 nM), 5 (IC50 = 3.23 nM) and 6 (IC50 = 7.12 nM) show higher activity than selegiline (IC50 = 19.60 nM) and higher MAO-B selectivity, with more than 9050-fold, 30,960-fold and 14,045-fold inhibition levels, with respect to the MAO-A isoform. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.013