(Z)-2(2,3-dimethoxybenzylidene)benzofuran-3(2H)-one | 111017-66-4

• 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)benzofuran-3(2H)-one
• 英文别名: 2-(2,3-dimethoxy-benzylidene)-benzofuran-3-one；2-(2,3-Dimethoxy-benzyliden)-benzofuran-3-on；(2Z)-2-[(2,3-dimethoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 111017-66-4
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: YPCAFRBKJPAXEZ-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2(2,3-dimethoxybenzylidene)benzofuran-3(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到(Z)-2-(2,3-dihydroxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Aurones as histone deacetylase inhibitors: Identification of key features

  摘要：

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.019
• 作为产物：
  描述：

  2,3-二甲氧基-2’-羟基查耳酮 在 mercury(II) diacetate 作用下， 以 吡啶 为溶剂， 反应 1.5h， 以74%的产率得到(Z)-2(2,3-dimethoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Aurones as histone deacetylase inhibitors: Identification of key features

  摘要：

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.019

文献信息

• Tambor; Gubler, Helvetica Chimica Acta, 1919, vol. 2, p. 107
  作者：Tambor、Gubler

  DOI：——

  日期：——
• Imafuku, Kimiaki; Honda, Masaaki; McOmie, J. F. W., Synthesis, 1987, # 2, p. 199 - 201
  作者：Imafuku, Kimiaki、Honda, Masaaki、McOmie, J. F. W.

  DOI：——

  日期：——
• IMAFUKU KIMIAKI; HONDA MASAAKI; MCOMIE J. F. W., SYNTHESIS,(1987) N 2, 199-201
  作者：IMAFUKU KIMIAKI、 HONDA MASAAKI、 MCOMIE J. F. W.

  DOI：——

  日期：——
• Aurones as histone deacetylase inhibitors: Identification of key features
  作者：Vincent Zwick、Alkiviadis-Orfefs Chatzivasileiou、Nathalie Deschamps、Marina Roussaki、Claudia A. Simões-Pires、Alessandra Nurisso、Iza Denis、Christophe Blanquart、Nadine Martinet、Pierre-Alain Carrupt、Anastasia Detsi、Muriel Cuendet

  DOI：10.1016/j.bmcl.2014.10.019

  日期：2014.12

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.