3-[6-(4-carboxyphenyl)amino-3,4-dihydroxyphenyl] propanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-[6-(4-carboxyphenyl)amino-3,4-dihydroxyphenyl] propanoic acid
• 英文别名: 3-[6-(4-carboxyphenyl)amino-3,4-dihydroxyphenyl]-propionic acid；4-[2-(2-Carboxyethyl)-4,5-dihydroxy-phenylamino)benzoicacid；4-[2-(2-carboxyethyl)-4,5-dihydroxyanilino]benzoic acid
• 化学式: C₁₆H₁₅NO₆
• 分子量: 317.298
• InChiKey: DMUDTYUPYPCEPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4-二羟基苯基丙酸 、 对氨基苯甲酸 以 acetate buffer 为溶剂， 反应 3.0h， 生成 3-[6-(4-carboxyphenyl)amino-3,4-dihydroxyphenyl] propanoic acid
  参考文献：
  名称：

  使用漆酶将胺N偶联合成3-（3,4-二羟基苯基）-丙酸衍生物

  摘要：

  天然化合物3-（3,4-二羟基苯基）-丙酸（二氢咖啡酸）的衍生化可以通过漆酶催化的芳族和脂族胺的N偶联来实现。将3-（3,4-二羟基苯基）-丙酸和4-氨基苯甲酸与漆酶一起在水性介质中和氧气存在下孵育，生成3- [6-（4-羧基苯基）氨基-3,4-二羟基苯基]-丙酸为主要产物（> 80％）。与己胺反应生成3-（6-己氨基-3,4-二羟基苯基）-丙酸作为唯一产物（60％）。

  DOI：

  10.1016/s0040-4020(02)00872-4

文献信息

• [EN] SUBSTITUTED ACIDS FOR THE TREATMENT OF RESPIRATORY DISEASES<br/>[FR] ACIDES SUBSTITUES POUR LE TRAITEMENT DE MALADIES RESPIRATOIRES
  申请人：ASTRAZENECA AB

  公开号：WO2006005909A1

  公开（公告）日：2006-01-19

  The invention relates to substituted acids of formula (I), where T,W,X,Y,Z,R1 and R2 as defined in the claims, as useful pharmaceutical compounds for treating asthma and rhinitis, pharmaceutical compositions containing them, and a processes for their preparation.

  该发明涉及公式（I）中T、W、X、Y、Z、R1和R2如权利要求中定义的取代酸，作为治疗哮喘和鼻炎的有用药物化合物，包含它们的药物组合物，以及它们的制备方法。
• Synthesis of 3-(3,4-dihydroxyphenyl)-propionic acid derivatives by N-coupling of amines using laccase
  作者：Annett Mikolasch、Elke Hammer、Ulrike Jonas、Katrin Popowski、Anne Stielow、Frieder Schauer

  DOI：10.1016/s0040-4020(02)00872-4

  日期：2002.9

  natural compound 3-(3,4-dihydroxyphenyl)-propionic acid (dihydrocaffeic acid) can be achieved by laccase-catalyzed N-coupling of aromatic and aliphatic amines. Incubation of 3-(3,4-dihydroxyphenyl)-propionic acid and 4-aminobenzoic acid with laccase in aqueous medium and in the presence of oxygen yielded 3-[6-(4-carboxyphenyl)amino-3,4-dihydroxyphenyl]-propionic acid as the main product (>80%). Reaction

  天然化合物3-（3,4-二羟基苯基）-丙酸（二氢咖啡酸）的衍生化可以通过漆酶催化的芳族和脂族胺的N偶联来实现。将3-（3,4-二羟基苯基）-丙酸和4-氨基苯甲酸与漆酶一起在水性介质中和氧气存在下孵育，生成3- [6-（4-羧基苯基）氨基-3,4-二羟基苯基]-丙酸为主要产物（> 80％）。与己胺反应生成3-（6-己氨基-3,4-二羟基苯基）-丙酸作为唯一产物（60％）。
• Substituted Acids for the Treatment of Respiratory Diseases
  申请人：Bonnert Victor Roger

  公开号：US20080114002A1

  公开（公告）日：2008-05-15

  The invention relates to substituted acids of formula (I), where T, W, X, Y, Z, R 1 and R 2 as defined in the claims, as useful pharmaceutical compounds for treating asthma and rhinitis, pharmaceutical compositions containing them, and a processes for their preparation.

  本发明涉及式（I）的取代酸，其中T，W，X，Y，Z，R1和R2如权利要求所定义，作为治疗哮喘和鼻炎的有用药物化合物，包含它们的制药组合物以及其制备方法。
• Selective oxidation and N-coupling by purified laccase of Xylaria polymorpha MTCC-1100
  作者：Pankaj Kumar Chaurasia、Sudha Yadava、Shashi Lata Bharati、Sunil Kumar Singh

  DOI：10.1134/s1068162014040025

  日期：2014.7

  The chemical route of oxidation of methyl group to its aldehyde is inconvenient because once a methyl group is attacked, it is likely to be oxidized to the carboxylic acid and it is very difficult to stop the reaction at the aldehyde stage. Fungal laccases can be used for such oxidation reaction and the reaction can be completed sharply within 1-2 hrs. Coupling of amines are another important reactions known forfungal laccases; coupling reactions generally take 3-7 hrs. We have used the purified laccase of molecular weight 63 kDa obtained from the fungal strainXylaria polymorpha MTCC-100 with activity of 1.95 IU/mL for selective oxidation of 2-fluorotoluene, 4-fluorotoluene, and 2-chlorotoluene to 2-fluorobenzaldehyde, 4-fluorobenzaldehyde, and 2-chlorobenzaldehyde, respectively, and syntheses of 3-(3,4-dihydroxyphenyl)-propionic acid derivatives by N-coupling of amines. In each oxidation reactions, ABTS was used as mediator molecule. All the syntheses are ecofriendly and were performed at room temperature.
• SUBSTITUTED ACIDS FOR THE TREATMENT OF RESPIRATORY DISEASES
  申请人：AstraZeneca AB

  公开号：EP1765768A1

  公开（公告）日：2007-03-28