(Z)-2-(3-methoxybenzylidene)-6-(2-(piperidin-1-yl)ethoxy)benzofuran-3(2H)-one hydrochloride

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-2-(3-methoxybenzylidene)-6-(2-(piperidin-1-yl)ethoxy)benzofuran-3(2H)-one hydrochloride
• 英文别名: (2Z)-2-[(3-methoxyphenyl)methylidene]-6-(2-piperidin-1-ylethoxy)-1-benzofuran-3-one;hydrochloride
• 化学式: C₂₃H₂₅NO₄*ClH
• 分子量: 415.917
• InChiKey: AMTYCQPCZIHCBB-YNYSCKANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-羟基-2H-苯并呋喃-3-酮 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 生成 (Z)-2-(3-methoxybenzylidene)-6-(2-(piperidin-1-yl)ethoxy)benzofuran-3(2H)-one hydrochloride
  参考文献：
  名称：

  Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors

  摘要：

  Alzheimer's disease (AD), a progressive and neurodegenerative disorder of the brain, is the most common cause of dementia among elderly people. To date, the successful therapeutic strategy to treat AD is maintaining the levels of acetylcholine by inhibiting acetylcholinesterase (AChE). In the present study, aurone derivatives were designed and synthesized as AChE inhibitors based on the lead structure of sulfuretin. Of those synthesized, compound 10d showed ca. 1700-fold and 6-fold higher AChE inhibitory activity than sulfuretin and galantamine, respectively. This compound also ameliorated scopolamine-induced memory deficit in mice when administered orally at the dose of 1 and 2 mg/kg. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.11.004

文献信息

• Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors
  作者：Young Hun Lee、Min Cheol Shin、Yong Don Yun、Seo Young Shin、Jong Min Kim、Jeong Moo Seo、Nam-Jung Kim、Jong Hoon Ryu、Yong Sup Lee

  DOI：10.1016/j.bmc.2014.11.004

  日期：2015.1

  Alzheimer's disease (AD), a progressive and neurodegenerative disorder of the brain, is the most common cause of dementia among elderly people. To date, the successful therapeutic strategy to treat AD is maintaining the levels of acetylcholine by inhibiting acetylcholinesterase (AChE). In the present study, aurone derivatives were designed and synthesized as AChE inhibitors based on the lead structure of sulfuretin. Of those synthesized, compound 10d showed ca. 1700-fold and 6-fold higher AChE inhibitory activity than sulfuretin and galantamine, respectively. This compound also ameliorated scopolamine-induced memory deficit in mice when administered orally at the dose of 1 and 2 mg/kg. (C) 2014 Published by Elsevier Ltd.