N-咖啡酰甘氨酸 | 62430-42-6

• 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
• 中文名称: N-咖啡酰甘氨酸
• 英文名称: N-caffeoylglycine
• 英文别名: N-Caffeylglycin；N-(E)-Caffeoyl-glycine；2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]acetic acid
• CAS: 62430-42-6
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: ADSZIGUFCCRNIO-DUXPYHPUSA-N

物化性质

• 熔点：
  177-178 °C(Solv: methanol (67-56-1))
• 沸点：
  624.9±55.0 °C(Predicted)
• 密度：
  1.474±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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 sodium hydroxide 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 肼 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 33.0h， 生成 N-咖啡酰甘氨酸
  参考文献：
  名称：

  Hanselaer, R.; D'Haenens, L.; Martens, M., Bulletin des Societes Chimiques Belges, 1983, vol. 92, # 11-12, p. 1029 - 1038

  摘要：

  DOI：

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。
• Use of a ferulic acid derivative as a preventive or remedy for hypertension
  申请人：Kao Corporation

  公开号：EP1264596A2

  公开（公告）日：2002-12-11

  Provided is use of a compound represented by the following formula (1) or (2): wherein, R1 and R2 are the same or different and each independently represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl, aryl, alkylaryl, aralkyl or acyl, R3 represents hydroxyl, ester bond residue or amide bond residue, R4 represents ester bond residue or an amide bond residue, or a pharmaceutically acceptable salt thereof (except ferulic acid) for preparing a preventive or remedy for hypertension. When the preventive or remedy for hypertension according to the present invention is administered, ferulic acid exists in the blood for a long period of time, thereby continuously suppressing a blood pressure rise. Moreover, the hypertension preventive or remedy according to the present invention has reduced in bitterness peculiar to ferulic acid, which enables patients to take it continuously.

  本发明提供了由下式（1）或（2）代表的化合物的用途： 其中，R1 和 R2 相同或不同，且各自独立地代表氢、烷基、烯基、环烷基、环烯基、烷氧基烷基、芳基、烷芳基、芳烷基或酰基，R3 代表羟基、酯键残基或酰胺键残基，R4 代表酯键残基或酰胺键残基，或其药学上可接受的盐（阿魏酸除外），用于制备高血压的预防剂或治疗剂。 服用本发明的高血压预防或治疗药物时，阿魏酸会长期存在于血液中，从而持续抑制血压升高。此外，根据本发明的高血压预防剂或治疗剂减少了阿魏酸特有的苦味，使患者能够持续服用。
• Preventive or remedy for hypertension
  申请人：KAO CORPORATION

  公开号：US20030220398A1

  公开（公告）日：2003-11-27

  Provided is a method of treating hypertension, which comprises administering an effective amount of a compound represented by the following formula (1) or (2): 1 wherein, R 1 and R 2 are the same or different and each independently represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, alkoxyalkyl, aryl, alkylaryl, aralkyl, or acyl, R 3 represents hydroxyl, ester bond residue, or amide bond residue, R 4 represents ester bond residue or amide bond residue, or a pharmaceutically acceptable salt thereof (except ferulic acid). When the preventive or remedy for hypertension according to the present invention is administered, ferulic acid exists in the blood for a long period of time, thereby continuously suppressing a blood pressure rise. Moreover, the hypertension preventive or remedy according to the present invention has reduced in bitterness peculiar to ferulic acid, which enables patients to take it continuously.

  本发明提供了一种治疗高血压的方法，该方法包括施用有效量的下式（1）或（2）所代表的化合物： 1 其中，R 1 和 R 2 相同或不同，且各自独立地代表氢、烷基、烯基、环烷基、环烯基、烷氧基烷基、芳基、烷芳基、芳烷基或酰基，R 3 代表羟基、酯键残基或酰胺键残基，R 4 代表酯键残基或酰胺键残基，或其药学上可接受的盐（阿魏酸除外）。 服用本发明的高血压预防或治疗药物时，阿魏酸会长期存在于血液中，从而持续抑制血压升高。此外，根据本发明的高血压预防剂或治疗剂减少了阿魏酸特有的苦味，使患者能够持续服用。
• 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.
• 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.