(E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-phenylacrylic acid | 1265206-61-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-phenylacrylic acid
• 英文别名: (E)-3-(3,5-ditert-butyl-4-hydroxyphenyl)-2-phenylprop-2-enoic acid
• CAS: 1265206-61-8
• 化学式: C₂₃H₂₈O₃
• 分子量: 352.474
• InChiKey: WGAJAWADKIWYGS-SFQUDFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙酸 、 3,5-二叔丁基-4-羟基苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 5.0h， 以72%的产率得到(E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-phenylacrylic acid
  参考文献：
  名称：

  Design, synthesis and pharmacobiological evaluation of novel acrylic acid derivatives acting as lipoxygenase and cyclooxygenase-1 inhibitors with antioxidant and anti-inflammatory activities

  摘要：

  A series of novel acrylic acid derivatives bearing at the 3 position thienyl, furfuryl and 3,5-ditert-butyl-4-hydroxyphenyl substituents have been designed, synthesized and tested as potential dual lipoxygenase/cyclooxygenase-1 (LOX/COX-1) inhibitors and as antioxidant and anti-inflammatory agents. Some compounds have shown moderate antioxidant and COX-1 inhibitory activities, very good anti-inflammatory activity and an inhibition of soybean lipoxygenase (LOX) higher than caffeic acid. In particular, compound 4I disclosed a moderate in vitro LOX inhibition with an IC50 = 100 mu M whereas compounds 1I and 2II exhibited the best, albeit poor, activity as COX-1 inhibition (75% inhibition at 100 mu M). Good radical scavenging properties were shown by compounds 4I, 3I and 1II. Docking simulations performed on LOX inhibitor 4I and COX-1 inhibitor 1I indicated that hydrophobic key interactions may govern the enzyme-inhibitor binding. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.035

文献信息

• Design, synthesis and pharmacobiological evaluation of novel acrylic acid derivatives acting as lipoxygenase and cyclooxygenase-1 inhibitors with antioxidant and anti-inflammatory activities
  作者：Eleni Pontiki、Dimitra Hadjipavlou-Litina、Konstantinos Litinas、Orazio Nicolotti、Angelo Carotti

  DOI：10.1016/j.ejmech.2010.10.035

  日期：2011.1

  A series of novel acrylic acid derivatives bearing at the 3 position thienyl, furfuryl and 3,5-ditert-butyl-4-hydroxyphenyl substituents have been designed, synthesized and tested as potential dual lipoxygenase/cyclooxygenase-1 (LOX/COX-1) inhibitors and as antioxidant and anti-inflammatory agents. Some compounds have shown moderate antioxidant and COX-1 inhibitory activities, very good anti-inflammatory activity and an inhibition of soybean lipoxygenase (LOX) higher than caffeic acid. In particular, compound 4I disclosed a moderate in vitro LOX inhibition with an IC50 = 100 mu M whereas compounds 1I and 2II exhibited the best, albeit poor, activity as COX-1 inhibition (75% inhibition at 100 mu M). Good radical scavenging properties were shown by compounds 4I, 3I and 1II. Docking simulations performed on LOX inhibitor 4I and COX-1 inhibitor 1I indicated that hydrophobic key interactions may govern the enzyme-inhibitor binding. (C) 2010 Elsevier Masson SAS. All rights reserved.