(E)-3-(3,4-dihydroxyphenyl)-N-(3-hydroxyphenyl)acrylamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(3,4-dihydroxyphenyl)-N-(3-hydroxyphenyl)acrylamide
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-N-(3-hydroxyphenyl)prop-2-enamide
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: TUCRGTOIEKYIRD-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 、 3-氨基苯酚 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以84%的产率得到(E)-3-(3,4-dihydroxyphenyl)-N-(3-hydroxyphenyl)acrylamide
  参考文献：
  名称：

  咖啡酸酰胺作为选择性MMP-2和MMP-9抑制剂的设计，合成和生物学评估

  摘要：

  战略，管理与卫生政策 临床前研究

  DOI：

  10.1002/ddr.21038

文献信息

• Synthesis and evaluation of caffeic acid amides as antioxidants
  作者：Padinchare Rajan、Irina Vedernikova、Paul Cos、Dirk Vanden Berghe、Koen Augustyns、Achiel Haemers

  DOI：10.1016/s0960-894x(00)00630-2

  日期：2001.1

  A series of amides of caffeic acid has been synthesised and their antioxidant properties evaluated as lipid peroxidation inhibitors. Anilides of caffeic acid were found to be very efficient antioxidants with IC50's of 0.3 microM.

  已经合成了一系列咖啡酸酰胺，并评估了它们的抗氧化性能作为脂质过氧化抑制剂。发现咖啡酸的苯甲酸酯是非常有效的抗氧化剂，IC50为0.3 microM。
• Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents
  作者：Chia-Cheng Hung、Wei-Jen Tsai、Li-Ming Yang Kuo、Yao-Haur Kuo

  DOI：10.1016/j.bmc.2004.11.055

  日期：2005.3.1

  A series of amides of caffeic acid were synthesized and evaluated for their anti-platelet and anti-oxidative activities. N-(2-Bromo-phenyl)-3-(3,4-dihydroxy-phenyl)-acrylamide (12) and N-(3-Bromo-phenyl)-3-(3,4-dihydroxy-phenyl)-acrylamide (13) exhibited potent inhibitory activity (IC50 = 5.8 and 6.7 muM, respectively) against arachidonic acid-induced (AA) platelet aggregation, comparable with invalid caffeic acid. Most of the synthesized caffeic acid anifides exhibited the promising anti-platelet aggregation in AA-induced assay and anti-oxidative activities. This study also exhibited that caffeic anilides displayed more potent anti-oxidative activity in the radical scavenging activity assay than trolox and vitamin E. (C) 2004 Elsevier Ltd. All rights reserved.
• Design, Synthesis and Biological Evaluation of Caffeic Acid Amides as Selective MMP-2 and MMP-9 Inhibitors
  作者：Zhi-Hao Shi、Nian-Guang Li、Qian-Ping Shi、Hao Tang、Yu-Ping Tang、Wei Li、Lian Yin、Jian-Ping Yang、Jin-Ao Duan

  DOI：10.1002/ddr.21038

  日期：2012.9

  Strategy, Management and Health Policy Preclinical Research

  战略，管理与卫生政策 临床前研究