3',4,4',6-(methoxymethoxy)aurone | 1202495-48-4

• 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: 3',4,4',6-(methoxymethoxy)aurone
• 英文别名: (2Z)-2-[3,4-bis(methoxymethoxy)benzylidene]-4,6-bis(methoxymethoxy)-1-benzofuran-3(2H)-one；3',4,4',6-Tetra(methoxymethyl)-aurone；(2Z)-2-[[3,4-bis(methoxymethoxy)phenyl]methylidene]-4,6-bis(methoxymethoxy)-1-benzofuran-3-one
• CAS: 1202495-48-4
• 化学式: C₂₃H₂₆O₁₀
• 分子量: 462.453
• InChiKey: XYPJLRMVXOEGIS-WNFQYIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3',4,4',6-(methoxymethoxy)aurone 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以88%的产率得到金色草素
  参考文献：
  名称：

  Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

  摘要：

  A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.002
• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.08h， 生成 3',4,4',6-(methoxymethoxy)aurone
  参考文献：
  名称：

  A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin

  摘要：

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.

  DOI：

  10.1055/s-0031-1291153

文献信息

• Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity
  作者：Anastasia Detsi、Maya Majdalani、Christos A. Kontogiorgis、Dimitra Hadjipavlou-Litina、Panagiotis Kefalas

  DOI：10.1016/j.bmc.2009.10.002

  日期：2009.12

  A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition. (C) 2009 Elsevier Ltd. All rights reserved.
• A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin
  作者：Zhixiang Xie、Ying Li、Xiaolong Zhao、Jie Liu

  DOI：10.1055/s-0031-1291153

  日期：2012.7

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.
• 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.