2-(4-hydroxy-3-methoxybenzylidene)benzofuran-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: 2-(4-hydroxy-3-methoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 2-[(4-Hydroxy-3-methoxyphenyl)methylidene]-1-benzofuran-3-one
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: KNIKQAVPAFENMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2′,4-dihydroxy-3-methoxychalcone 在 吡啶 、 mercury(II) diacetate 作用下， 反应 1.0h， 以70%的产率得到2-(4-hydroxy-3-methoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

  摘要：

  A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.02.009

文献信息

• Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives
  作者：Vishnu Nayak Badavath、Chandrani Nath、Narayana Murthy Ganta、Gulberk Ucar、Barij Nayan Sinha、Venkatesan Jayaprakash

  DOI：10.1016/j.cclet.2017.02.009

  日期：2017.7

  A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1-20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1-5, 7-17, 19) were found to be selective towards hMAO-B, while two were non -selective (6 and 20) and one (18) selective towards hMAO-A. Compound 17 (Ki = 0.10 +/- 0.01 mu mol/L) was found to be equally potent and selective towards hMAO-B, when compared with the standard drug Selegiline (Ki = 0.12 0.01 p.mol/L). Nature and position of substitution in aryl ring at 2nd position of benzofuranone influences hMAO-B inhibitory potency, while their structural bulkiness influences selectivity between hMAO-A and hMAO-B. Molecular docking simulation was also carried out to understand the interaction of inhibitor with the enzyme at molecular level, and we found the docking results were in good agreement with the experimental values. Comparison of the activity profile of the aurones with their corresponding flavones reported earlier by our group revealed that there exists no difference in potency as well as selectivity. (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.