3-hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-5-(3,4-dimethoxyphenyl)penta-2,4-dien-1-one | 1196971-30-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-5-(3,4-dimethoxyphenyl)penta-2,4-dien-1-one
• CAS: 1196971-30-8
• 化学式: C₂₁H₂₂O₇
• 分子量: 386.401
• InChiKey: JBNCOHQMAKTTCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  94.45
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-5-(3,4-dimethoxyphenyl)penta-2,4-dien-1-one 在 对甲苯磺酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 以62%的产率得到(E)-3',4',7,8-tetramethoxy-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
• 作为产物：
  描述：

  (E)-3',4'-dimethoxy-2'-(3,4-dimethoxycinnamoyloxy)acetophenone 在 potassium hydroxide 、 盐酸 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 2.0h， 以62%的产率得到3-hydroxy-1-(2-hydroxy-3,4-dimethoxyphenyl)-5-(3,4-dimethoxyphenyl)penta-2,4-dien-1-one
  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