(Z)-2-(2,3-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one

• 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-(2,3-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one
• 英文别名: (2Z)-2-(2,3-dimethoxybenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one；(2Z)-2-[(2,3-dimethoxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one
• 化学式: C₁₇H₁₄O₅
• mdl: MFCD04142368
• 分子量: 298.295
• InChiKey: GQSYGPPHMQKVOE-NVNXTCNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.117
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-2-(2,3-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one 、 N-(3-氯丙基)吡咯烷盐酸盐 在 potassium carbonate 、 乙醇 、 乙酰氯 作用下， 以 丙酮 为溶剂， 以101 mg的产率得到(Z)-2-(2,3-dimethoxybenzylidene)-6-(3-(pyrrolidin-1-yl)propoxy)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
• 作为产物：
  描述：

  6-羟基-2H-苯并呋喃-3-酮 、 2,3-二甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-2-(2,3-dimethoxybenzylidene)-6-hydroxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones

  摘要：

  uAminomethylation of aurones was studied by using anabasine. The reaction in the case of 6-hydroxyaurones was shown to selectively provide 7-aminomethyl-6-hydroxyaurones, while 5-aminomethyl-6-hydroxy-7-methylaurones could be obtained by transamination of 5-dimethylaminomethyl derivatives of 6-hydroxy-7-methylaurones in the presence of anabasine.

  DOI：

  10.1007/s10593-019-02444-2

文献信息

• Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones
  作者：Antonina V. Popova、Svitlana P. Bondarenko、Valentina I. Vinogradova、Mykhaylo S. Frasinyuk

  DOI：10.1007/s10593-019-02444-2

  日期：2019.3

  uAminomethylation of aurones was studied by using anabasine. The reaction in the case of 6-hydroxyaurones was shown to selectively provide 7-aminomethyl-6-hydroxyaurones, while 5-aminomethyl-6-hydroxy-7-methylaurones could be obtained by transamination of 5-dimethylaminomethyl derivatives of 6-hydroxy-7-methylaurones in the presence of anabasine.
• 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.
• Design, synthesis, and repurposing of O-aminoalkyl-sulfuretin analogs towards discovery of potential lead compounds as antileishmanial agents
  作者：Ahmed H.E. Hassan、Trong-Nhat Phan、Suyeon Moon、Chae Hyeon Lee、Yeon Ju Kim、Soo Bin Cho、Selwan M. El-Sayed、Yeonwoo Choi、Joo Hwan No、Yong Sup Lee

  DOI：10.1016/j.ejmech.2023.115256

  日期：2023.5