7-(3-(benzyl(ethyl)amino)propoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one | 1439912-98-7

• 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: 7-(3-(benzyl(ethyl)amino)propoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 7-[3-[Benzyl(ethyl)amino]propoxy]-5-hydroxy-3-(4-hydroxyphenyl)chromen-4-one；7-[3-[benzyl(ethyl)amino]propoxy]-5-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 1439912-98-7
• 化学式: C₂₇H₂₇NO₅
• 分子量: 445.515
• InChiKey: STWYDJBHZCAVTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  染料木素 在 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 7-(3-(benzyl(ethyl)amino)propoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and evaluation of genistein-O-alkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease

  摘要：

  A series of genistein derivatives with carbon spacer-linked alkylbenzylamines were designed, synthesized and tested as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good acetylcholinesterase (AChE) inhibitory activity, with moderate-to-good anti-oxidative activity. Specifically, compounds 10b, 19d and 254 exhibited significant inhibition of beta-amyloid (A beta) aggregation and exhibited metal chelating properties. In particular, 25d inhibited: self-induced A beta(1-42) aggregation, Cu2+-induced A beta(1-42) aggregation, and human AChE-induced A beta(1-40) aggregation by 35%, 77.8%, and 36.2%, respectively. Moreover, both kinetic analysis of AChE inhibition and the molecular modeling study suggested that 25d binds simultaneously to catalytic active site and peripheral anionic site of AChE. More importantly, compound 25d disassembled the well-structured A beta fibrils generated by Cu2+-induced A beta aggregation by 72.1%. Furthermore, the step-down passive avoidance test showed this compound significantly reversed scopolamine-induced memory deficit in mice. These results suggest that 25d may be a promising multifunctional agent for AD treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.045

文献信息

• Design, synthesis and evaluation of genistein-O-alkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease
  作者：Xiaoming Qiang、Zhipei Sang、Wen Yuan、Yan Li、Qiang Liu、Ping Bai、Yikun Shi、Wei Ang、Zhenghuai Tan、Yong Deng

  DOI：10.1016/j.ejmech.2014.02.045

  日期：2014.4

  A series of genistein derivatives with carbon spacer-linked alkylbenzylamines were designed, synthesized and tested as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good acetylcholinesterase (AChE) inhibitory activity, with moderate-to-good anti-oxidative activity. Specifically, compounds 10b, 19d and 254 exhibited significant inhibition of beta-amyloid (A beta) aggregation and exhibited metal chelating properties. In particular, 25d inhibited: self-induced A beta(1-42) aggregation, Cu2+-induced A beta(1-42) aggregation, and human AChE-induced A beta(1-40) aggregation by 35%, 77.8%, and 36.2%, respectively. Moreover, both kinetic analysis of AChE inhibition and the molecular modeling study suggested that 25d binds simultaneously to catalytic active site and peripheral anionic site of AChE. More importantly, compound 25d disassembled the well-structured A beta fibrils generated by Cu2+-induced A beta aggregation by 72.1%. Furthermore, the step-down passive avoidance test showed this compound significantly reversed scopolamine-induced memory deficit in mice. These results suggest that 25d may be a promising multifunctional agent for AD treatment. (C) 2014 Elsevier Masson SAS. All rights reserved.