2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid | 959927-45-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid
• 英文别名: N-(E)-Caffeoyl-L-alanine；(2S)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propanoic acid
• CAS: 959927-45-8
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: HTRLGQVZCDCTDC-MZTFZBDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 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：

  2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以30%的产率得到2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-propionic acid
  参考文献：
  名称：

  Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of l-chicoric acid, as new HIV-1 integrase inhibitors

  摘要：

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. L-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures Of L-chicoric acid 2 were synthesized for the purpose of simplifying the structure Of L-Chicoric acid. Among synthesized, compounds 2c and 3f showed HIV-1 IN inhibitory activities with IC50 values of 10.5 and 12.0 mu M, respectively, comparable to that of parent compound L-chicoric acid (IC50 = 15.7 mu M). (c) 2007 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.016

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.
• Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of l-chicoric acid, as new HIV-1 integrase inhibitors
  作者：Seung Uk Lee、Cha-Gyun Shin、Chong-Kyo Lee、Yong Sup Lee

  DOI：10.1016/j.ejmech.2007.02.016

  日期：2007.10

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. L-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures Of L-chicoric acid 2 were synthesized for the purpose of simplifying the structure Of L-Chicoric acid. Among synthesized, compounds 2c and 3f showed HIV-1 IN inhibitory activities with IC50 values of 10.5 and 12.0 mu M, respectively, comparable to that of parent compound L-chicoric acid (IC50 = 15.7 mu M). (c) 2007 Elsevier Masson SAS. All fights reserved.