(E)-3-(3-(3,4-dihydroxyphenyl)acrylamido)propanoic acid | 675833-41-7

• 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-(3,4-dihydroxyphenyl)acrylamido)propanoic acid
• 英文别名: N-Caffeoyl-beta-alanine；3-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propanoic acid
• CAS: 675833-41-7
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: WPBOFJOMOJATDP-DUXPYHPUSA-N

物化性质

• 熔点：
  185 °C(Solv: methanol (67-56-1))
• 沸点：
  623.0±55.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 在 吡啶 、 甲醇 、 草酰氯 、 碳酸氢钠 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.25h， 生成  (E)-3-(3-(3,4-dihydroxyphenyl)acrylamido)propanoic acid
  参考文献：
  名称：

  Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors

  摘要：

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.033

文献信息

• MICROBIOLOGICAL METHOD FOR SYNTHESIZING CINNAMOYL AMIDE DERIVATIVES OF AMINO ACIDS
  申请人：Lorquin Jean

  公开号：US20120142778A1

  公开（公告）日：2012-06-07

  Method for the microbiological production of cinnamoyl amide derivatives of amino acids, certain products that result therefrom and uses thereof, especially as antioxidants.

  微生物生产氨基酸肉桂酰胺衍生物的方法，以及由此产生的某些产品及其用途，特别是作为抗氧化剂。
• PROCEDE MICROBIOLOGIQUE DE SYNTHESE DE DERIVES CINNAMOYL AMIDES D'ACIDES AMINES
  申请人：Institut De Recherche Pour Le Developpement

  公开号：EP2303830A1

  公开（公告）日：2011-04-06
• US8497302B2
  申请人：——

  公开号：US8497302B2

  公开（公告）日：2013-07-30
• [EN] MICROBIOLOGICAL METHOD FOR SYNTHESIZING CINNAMOYL AMIDE DERIVATIVES OF AMINO ACIDS<br/>[FR] PROCEDE MICROBIOLOGIQUE DE SYNTHESE DE DERIVES CINNAMOYL AMIDES D'ACIDES AMINES
  申请人：INST RECH DEVELOPPEMENT IRD

  公开号：WO2010000964A1

  公开（公告）日：2010-01-07

  Procédé de production microbiologique de dérivés de cinnamoyl amides d'acides aminés, certains produits en résultant et leurs utilisations, notamment comme antioxydants.
• Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors
  作者：Yuanchao Xie、Bing Huang、Kexiang Yu、Fangyuan Shi、Tianqi Liu、Wenfang Xu

  DOI：10.1016/j.bmcl.2013.04.033

  日期：2013.6

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.