3-(3',5'-dimethoxy)phenyl-6-methylcoumarin | 1173998-03-2

• 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: 3-(3',5'-dimethoxy)phenyl-6-methylcoumarin
• 英文别名: 3-(3'',5''-Dimethoxy)phenyl-6-methylcumarin；3-(3,5-dimethoxyphenyl)-6-methylchromen-2-one
• CAS: 1173998-03-2
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: ZFSYKJRFFGNQCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3',5'-dimethoxy)phenyl-6-methylcoumarin 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 18.0h， 以46%的产率得到3-(2-bromo-3,5-dimethoxyphenyl)-6-methylcoumarin
  参考文献：
  名称：

  Synthesis and Study of a Series of 3-Arylcoumarins as Potent and Selective Monoamine Oxidase B Inhibitors

  摘要：

  New series of 6-substituted-3-arylcoumarins displaying several alkyl, hydroxyl, halogen, and alkoxy groups in the two benzene rings have been designed, synthesized, and evaluated in vitro as human monoamine cuddase A and B (hMAO-A and hMAO-B) inhibitors. Most of the studied compounds showed a high affinity and selectivity to the hMAO-B isoenzyme, with IC50 values on nanomolar and picomolar range. Ten of the 22 described compounds displayed higher MAO-B inhibitory activity and selectivity than selegiline. Coumarin 7 is the most active compound of this series, being 64 times more active than selegiline and also showing the highest hMAO-B specificity. In addition, docking experiments were carried out on hMAO-A and h-MAO-B structures. This study provided new information about the enzyme inhibitor interaction and the potential therapeutic application of this 3-arylcoumarin scaffold.

  DOI：

  10.1021/jm200716y
• 作为产物：
  描述：

  5-甲基水杨醛 、 (3,5-二甲氧基苯基)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60%的产率得到3-(3',5'-dimethoxy)phenyl-6-methylcoumarin
  参考文献：
  名称：

  A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors

  摘要：

  6-Methyl-3-phenylcoumarins 3-6 were designed, synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. The synthesis of these new compounds (resveratrol-coumarin hybrids) was carried out with good yield by a Perkin reaction, from the 5-methylsalicylaldehyde and the corresponding phenylacetic acid. They show high selectivity to the MAO-B isoenzyme, with IC(50) values in the nanomolar range. Compound 5 is the most active compound and is several times more potent and selective than the reference compound, R-(-)-deprenyl. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.085