Caffeic Acid 3,4-Dimethoxyphenyl Amide | 136944-22-4

• 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: Caffeic Acid 3,4-Dimethoxyphenyl Amide
• 英文别名: (E)-3-(3,4-Dihydroxyphenyl)-N-(3,4-dimethoxyphenyl)prop-2-enamide
• CAS: 136944-22-4
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: DEOHUSDXNWMAHF-XBXARRHUSA-N

物化性质

• 熔点：
  201 °C
• 沸点：
  574.0±50.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 、 3,4-二甲氧基苯胺 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以73%的产率得到Caffeic Acid 3,4-Dimethoxyphenyl Amide
  参考文献：
  名称：

  Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2004.11.055

文献信息

• 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.