7-(4-(4-(2-hydroxyphenyl)piperazin-1-yl)-4-oxobutoxy)-4-methyl-2H-chromen-2-one | 1618668-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 7-(4-(4-(2-hydroxyphenyl)piperazin-1-yl)-4-oxobutoxy)-4-methyl-2H-chromen-2-one
• 英文别名: 7-[4-[4-(2-Hydroxyphenyl)piperazin-1-yl]-4-oxobutoxy]-4-methylchromen-2-one；7-[4-[4-(2-hydroxyphenyl)piperazin-1-yl]-4-oxobutoxy]-4-methylchromen-2-one
• CAS: 1618668-16-8
• 化学式: C₂₄H₂₆N₂O₅
• 分子量: 422.481
• InChiKey: SYBPUPHIQWIZSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 4-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)butanoate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 29.0h， 生成 7-(4-(4-(2-hydroxyphenyl)piperazin-1-yl)-4-oxobutoxy)-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis and anti-cholinesterase activity of new 7-hydroxycoumarin derivatives

  摘要：

  A series of 7-hydroxycoumarin derivatives connected by an amidic linker to the different amines were designed and synthesized as cholinesterase inhibitors. Most compounds showed remarkable inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among them, N-(1-benzylpiperidin-4-yl)acetamide derivative 4r with IC50 value of 1.6 mu M was the most potent compound against AChE. The selectivity index of compound 4r for anti-AChE activity was about 26. Moreover, the compound 4r significantly protected PC12 neurons against H2O2-induced cell death at low concentrations. The docking study of compound 4r with AChE enzyme showed that both CAS and PAS are occupied by the ligand. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.056

文献信息

• Synthesis and anti-cholinesterase activity of new 7-hydroxycoumarin derivatives
  作者：Masoumeh Alipour、Mehdi Khoobi、Alireza Moradi、Hamid Nadri、Farshad Homayouni Moghadam、Saeed Emami、Zeinab Hasanpour、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2014.05.056

  日期：2014.7

  A series of 7-hydroxycoumarin derivatives connected by an amidic linker to the different amines were designed and synthesized as cholinesterase inhibitors. Most compounds showed remarkable inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among them, N-(1-benzylpiperidin-4-yl)acetamide derivative 4r with IC50 value of 1.6 mu M was the most potent compound against AChE. The selectivity index of compound 4r for anti-AChE activity was about 26. Moreover, the compound 4r significantly protected PC12 neurons against H2O2-induced cell death at low concentrations. The docking study of compound 4r with AChE enzyme showed that both CAS and PAS are occupied by the ligand. (C) 2014 Elsevier Masson SAS. All rights reserved.