N-[2-(1-benzylpiperidin-4-yl)ethyl]-7-methoxy-2-oxo-2H-chromene-3-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-[2-(1-benzylpiperidin-4-yl)ethyl]-7-methoxy-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-[2-(1-benzylpiperidin-4-yl)ethyl]-7-methoxy-2-oxochromene-3-carboxamide
• 化学式: C₂₅H₂₈N₂O₄
• 分子量: 420.508
• InChiKey: BOYUHPHGPUPZAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(1-苄基-4-哌啶)乙腈 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 N-[2-(1-benzylpiperidin-4-yl)ethyl]-7-methoxy-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors

  摘要：

  Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.024

文献信息

• Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors
  作者：Ali Asadipour、Masoumeh Alipour、Mona Jafari、Mehdi Khoobi、Saeed Emami、Hamid Nadri、Amirhossein Sakhteman、Alireza Moradi、Vahid Sheibani、Farshad Homayouni Moghadam、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2013.10.024

  日期：2013.12

  Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study. (C) 2013 Elsevier Masson SAS. All rights reserved.