(E)-1-(4-(2-(diethylamino)ethoxy)phenyl)-3-phenylprop-2-en-1-one | 25960-41-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4-(2-(diethylamino)ethoxy)phenyl)-3-phenylprop-2-en-1-one
• 英文别名: 4'-(2-diethylamino-ethoxy)-trans-chalcone；4'-(2-Diaethylamino-aethoxy)-trans-chalkon；(E)-1-[4-[2-(diethylamino)ethoxy]phenyl]-3-phenylprop-2-en-1-one
• CAS: 25960-41-2
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: LZBQTJUASOHOGJ-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl magnesium iodide 、 (E)-1-(4-(2-(diethylamino)ethoxy)phenyl)-3-phenylprop-2-en-1-one 在 乙醚 作用下， 生成 1-[4-(2-diethylamino-ethoxy)-phenyl]-3-phenyl-pentan-1-one
  参考文献：
  名称：

  Derivatives of 4(diethylaminoethoxy)-diphenylpropane

  摘要：

  公开号：

  US02796435A1
• 作为产物：
  描述：

  (E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one 在 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 (E)-1-(4-(2-(diethylamino)ethoxy)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of chalcone derivatives as acetylcholinesterase inhibitors

  摘要：

  A novel series of chalcone derivatives (4a-8d) were designed, synthesized, and evaluated for the inhibition activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The logP values of the compounds were shown to range from 1.49 to 2.19, which suggested that they were possible to pass blood brain barriers in vivo. The most promising compound 4a (IC50: 4.68 mu mol/L) was 2-fold more potent than Rivastigmine against AChE (IC50: 10.54 mu mol/L) and showed a high selectivity for AChE over BuChE (ratio: 4.35). Enzyme kinetic study suggested that the inhibition mechanism of compound 4a was a mixed-type inhibition. Meanwhile, the result of molecular docking showed its potent inhibition of AChE and high selectivity for AChE over BuChE. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.08.033

文献信息

• Derivatives of 4(diethylaminoethoxy)-diphenylpropane
  申请人：HOFFMANN LA ROCHE

  公开号：US02796435A1

  公开（公告）日：1957-06-18
• Design, synthesis and pharmacological evaluation of chalcone derivatives as acetylcholinesterase inhibitors
  作者：Hao-ran Liu、Xian-jun Liu、Hao-qun Fan、Jing-jing Tang、Xiao-hui Gao、Wu-Kun Liu

  DOI：10.1016/j.bmc.2014.08.033

  日期：2014.11

  A novel series of chalcone derivatives (4a-8d) were designed, synthesized, and evaluated for the inhibition activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). The logP values of the compounds were shown to range from 1.49 to 2.19, which suggested that they were possible to pass blood brain barriers in vivo. The most promising compound 4a (IC50: 4.68 mu mol/L) was 2-fold more potent than Rivastigmine against AChE (IC50: 10.54 mu mol/L) and showed a high selectivity for AChE over BuChE (ratio: 4.35). Enzyme kinetic study suggested that the inhibition mechanism of compound 4a was a mixed-type inhibition. Meanwhile, the result of molecular docking showed its potent inhibition of AChE and high selectivity for AChE over BuChE. (C) 2014 Elsevier Ltd. All rights reserved.