7-(4-(benzyl(methyl)amino)butoxy)-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-(4-(benzyl(methyl)amino)butoxy)-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one
• 英文别名: 7-[4-[Benzyl(methyl)amino]butoxy]-2-[4-(dimethylamino)phenyl]chromen-4-one；7-[4-[benzyl(methyl)amino]butoxy]-2-[4-(dimethylamino)phenyl]chromen-4-one
• 化学式: C₂₉H₃₂N₂O₃
• 分子量: 456.585
• InChiKey: AQXHNJKXLYVXMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯-1-(2,4-二羟基苯基)乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 42.0h， 生成 7-(4-(benzyl(methyl)amino)butoxy)-2-(4-(dimethylamino)phenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and evaluation of novel 4-dimethylamine flavonoid derivatives as potential multi-functional anti-Alzheimer agents

  摘要：

  A series of 4-dimethylamine flavonoid derivatives 5a-5r were designed, synthesized and evaluated as potential multi-functional anti-Alzheimer agents. The results showed that most of the synthesized compounds exhibited high acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity at the micromolar range (IC50, 1.83-33.20 mu M for AChE and 0.82-11.45 mu M for BChE). A Lineweaver-Burk plot indicated a mixed-type inhibition for compound 5j with AChE, and molecular modeling study showed that 5j targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Besides, the derivatives showed potent self-induced A beta aggregation inhibitory activity at 20 mu M with percentage from 25% to 48%. In addition, some compounds (5j-5q) showed potent oxygen radical absorbance capacity (ORAC) ranging from 1.5- to 2.6-fold of the Trolox value. These compounds should be further investigated as multi-potent agents for the treatment of Alzheimer's disease. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.061

文献信息

• Design, synthesis and evaluation of novel 4-dimethylamine flavonoid derivatives as potential multi-functional anti-Alzheimer agents
  作者：Wen Luo、Ya-Bin Su、Chen Hong、Run-Guo Tian、Lei-Peng Su、Yue-Qiao Wang、Yang Li、Jun-Jie Yue、Chao-Jie Wang

  DOI：10.1016/j.bmc.2013.09.061

  日期：2013.12

  A series of 4-dimethylamine flavonoid derivatives 5a-5r were designed, synthesized and evaluated as potential multi-functional anti-Alzheimer agents. The results showed that most of the synthesized compounds exhibited high acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity at the micromolar range (IC50, 1.83-33.20 mu M for AChE and 0.82-11.45 mu M for BChE). A Lineweaver-Burk plot indicated a mixed-type inhibition for compound 5j with AChE, and molecular modeling study showed that 5j targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Besides, the derivatives showed potent self-induced A beta aggregation inhibitory activity at 20 mu M with percentage from 25% to 48%. In addition, some compounds (5j-5q) showed potent oxygen radical absorbance capacity (ORAC) ranging from 1.5- to 2.6-fold of the Trolox value. These compounds should be further investigated as multi-potent agents for the treatment of Alzheimer's disease. (C) 2013 Elsevier Ltd. All rights reserved.