(E)-3',4'-dihydroxy-7,8-dimethoxy-2-styrylchromone | 1196971-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-3',4'-dihydroxy-7,8-dimethoxy-2-styrylchromone
• 英文别名: 2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-7,8-dimethoxychromen-4-one
• CAS: 1196971-16-0
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: KDDLEILPCASNFH-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-3',4'-dibenzyloxy-7,8-dimethoxy-2-styrylchromone 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.5h， 以82%的产率得到(E)-3',4'-dihydroxy-7,8-dimethoxy-2-styrylchromone
  参考文献：
  名称：

  Synthesis and antioxidant properties of new chromone derivatives

  摘要：

  Nowadays, the recognition of the benefits of antioxidants is eliciting an increasingly interest in the search for new molecules with improved activity. The aim of the present work was to search for improved reactive oxygen species (ROS) and reactive nitrogen species (RNS) scavengers by testing new structures of 2-styrylchromones (2-SC) and 3-substituted flavones, which were synthesised by the Baker-Venkataraman approach. The new compounds were also tested for their metal chelating capacity and reducing activity. The obtained results showed that the methylation of hydroxyl groups decreases the scavenging of ROS and RNS by 2-SC. The decrease in the scavenging activities was, generally, more evident when the methylation occurred in B-ring, except for O-2(center dot-) and O-1(2). On the other hand, the introduction of a substituent, either hydroxyl or methoxyl, in position 8 was sometimes favourable and others unfavourable to the scavenging activities, depending on the reactive species. In conclusion, the study of the antioxidant properties of the new 2-SC and flavones allowed establishing new structure-activity relationships and brought out, in some cases, pharmacophores with improved activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.056

文献信息

• Synthesis and antioxidant properties of new chromone derivatives
  作者：Ana Gomes、Ondrej Neuwirth、Marisa Freitas、Diana Couto、Daniela Ribeiro、Andrea G.P.R. Figueiredo、Artur M.S. Silva、Raquel S.G.R. Seixas、Diana C.G.A. Pinto、Augusto C. Tomé、José A.S. Cavaleiro、Eduarda Fernandes、José L.F.C. Lima

  DOI：10.1016/j.bmc.2009.08.056

  日期：2009.10

  Nowadays, the recognition of the benefits of antioxidants is eliciting an increasingly interest in the search for new molecules with improved activity. The aim of the present work was to search for improved reactive oxygen species (ROS) and reactive nitrogen species (RNS) scavengers by testing new structures of 2-styrylchromones (2-SC) and 3-substituted flavones, which were synthesised by the Baker-Venkataraman approach. The new compounds were also tested for their metal chelating capacity and reducing activity. The obtained results showed that the methylation of hydroxyl groups decreases the scavenging of ROS and RNS by 2-SC. The decrease in the scavenging activities was, generally, more evident when the methylation occurred in B-ring, except for O-2(center dot-) and O-1(2). On the other hand, the introduction of a substituent, either hydroxyl or methoxyl, in position 8 was sometimes favourable and others unfavourable to the scavenging activities, depending on the reactive species. In conclusion, the study of the antioxidant properties of the new 2-SC and flavones allowed establishing new structure-activity relationships and brought out, in some cases, pharmacophores with improved activity. (C) 2009 Elsevier Ltd. All rights reserved.