caffeoyl-N-tryptophan | 109163-69-1

• 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: caffeoyl-N-tryptophan
• 英文别名: (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tryptophan；Caffeoyltryptophan；(2S)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 109163-69-1
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: XITPERBRJNUFSB-BVBGJJFLSA-N

物化性质

• 沸点：
  771.3±60.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  123
• 氢给体数：
  5
• 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 caffeoyl-N-tryptophan
  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

• AMINO ACID DERIVATIVE
  申请人：Ookubo Tomohiro

  公开号：US20110172442A1

  公开（公告）日：2011-07-14

  The amino acid derivative of the present invention provides a novel compound that shows excellent analgesic action. The amino acid derivative of the present invention is a novel compound that shows excellent analgesic action to not only a model animal for nociceptive pains but also a model animal for neuropathic pains, so that the amino acid derivative is very useful as a drug for treating various pain diseases.

  本发明的氨基酸衍生物提供了一种显示出优异镇痛作用的新化合物。本发明的氨基酸衍生物是一种新化合物，不仅对于模拟伤害性疼痛的动物模型，而且对于模拟神经病理性疼痛的动物模型都显示出优异的镇痛作用，因此该氨基酸衍生物作为治疗各种疼痛疾病的药物非常有用。
• Hydroxycinnamoyl Amino Acids Conjugates: A Chiral Pool to Distinguish Commercially Exploited Coffea spp.
  作者：Federico Berti、Luciano Navarini、Silvia Colomban、Cristina Forzato

  DOI：10.3390/molecules25071704

  日期：——

  The synthesis of five hydroxycinnamoyl amides (HCAs) was accomplished and their identification and quantification in the green coffee bean samples of Coffea arabica, Coffea canephora, and Coffea liberica was performed. The HCAs p-coumaroyl-N-tyrosine 1b, caffeoyl-N-phenylalanine 2b, caffeoyl-N-tyrosine 3b, and p-coumaroyl-N-tryptophan 4b were characteristic of the C. canephora species while caffeoyl-N-tryptophan 5b was present in both C. canephora and C. arabica, but with higher content in C. canephora. The HCAs presence was also analyzed in C. liberica for the first time and none of the targeted compounds was found, indicating that this species is very similar to C. arabica species. Between C. canephora samples from various origins, significant differences were observed regarding the presence of all the HCAs, with C. canephora from Tanzania containing all five derivatives.

  合成了五种羟基肉桂酰胺（HCAs），并对咖啡属（Coffea arabica，Coffea canephora和Coffea liberica）的绿咖啡豆样品进行了它们的鉴定和定量。HCAs对C. canephora物种具有特征性，其中p-香豆酰-N-酪氨酸1b，咖啡酰-N-苯丙氨酸2b，咖啡酰-N-酪氨酸3b和p-香豆酰-N-色氨酸4b。咖啡酰-N-色氨酸5b存在于C. canephora和C. arabica中，但在C. canephora中含量更高。首次分析了C. liberica中的HCAs存在，并且没有发现任何目标化合物，表明该物种与C. arabica物种非常相似。在来自不同地区的C. canephora样品中，观察到所有HCAs的存在方面存在显着差异，坦桑尼亚的C. canephora含有所有五种衍生物。
• Coffee flavour modification process
  申请人：Kraft Foods R & D, Inc. Zweigniederlassung München

  公开号：EP1872665A1

  公开（公告）日：2008-01-02

  The invention relates to a process for improving the flavour of roasted Robusta and Arabica quality coffee and is characterised by modifying roasted coffee flavour precursors in aqueous extracts of green coffee beans.

  本发明涉及一种改善烘焙罗布斯塔和阿拉比卡优质咖啡风味的工艺，其特点是改变绿咖啡豆水提取物中的烘焙咖啡风味前体。
• Effects of a decaffeinated green coffee extract on body weight control by regulation of glucose metabolism
  申请人：NATUREX, S.A.

  公开号：US10092613B2

  公开（公告）日：2018-10-09

  A method of controlling body weight in humans by administering an amount of decaffeinated green coffee extract effective to treat a subject. A preferred green coffee extract contains a ratio of 4-caffeoylquinic acid (4-CQA) to total chlorogenic acids (tCGA) (5-CQA/tCGA) of from about 0.1 to about 0.2. More preferably, the green coffee extract comprises from about 6% to about 8% of 4-caffeoylquinic acid and has a total chlorogenic acid concentration that exceeds about 45%. A preferred method of administration consists of administering the green coffee extracts is a dosage of about 200 mg twice a day prior to meals on an empty stomach.

  一种控制人体体重的方法，通过施用一定量的低咖啡因绿咖啡提取物来有效治疗受试者。一种优选的绿咖啡提取物中，4-咖啡酰奎宁酸（4-CQA）与总绿原酸（tCGA）（5-CQA/tCGA）之比约为 0.1 至 0.2。更优选的是，绿咖啡提取物包含约 6%至约 8%的 4-咖啡酰奎宁酸，且绿原酸总浓度超过约 45%。一种优选的给药方法是空腹在饭前服用绿咖啡提取物，每天两次，每次约 200 毫克。
• MEDIZINISCHE VERWENDUNG VON N-PHENYLPROPENOYL-AMINOSÄUREDERIVATEN
  申请人：Westfälische Wilhelms-Universität Münster

  公开号：EP2040692B1

  公开（公告）日：2012-09-19