N-trans-caffeoyl-L-phenylalanine | 170663-16-8

• 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: N-trans-caffeoyl-L-phenylalanine
• 英文别名: 2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]-3-phenylpropionic acid；(S,E)-2-(3-(3,4-dihydroxyphenyl)acrylamido)-3-phenylpropanoic acid；caffeoyl phenylalanine；(-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-phenylalanine；caffeoyl-N-phenylalanine；N-Caffeoylalanine；(2S)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-3-phenylpropanoic acid
• CAS: 170663-16-8
• 化学式: C₁₈H₁₇NO₅
• 分子量: 327.337
• InChiKey: QPJDGIIOGMCKTH-KGXGESDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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 N-trans-caffeoyl-L-phenylalanine
  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

• Structure-activity relationship of clovamide and its related compounds for the inhibition of amyloid β aggregation
  作者：Tatsuhiko Tsunoda、Mio Takase、Hideyuki Shigemori

  DOI：10.1016/j.bmc.2018.04.044

  日期：2018.7

  the structure-activity relationship of clovamide (1) for the inhibition of Aβ aggregation, we synthesized 1 and related compounds 2-11 through reaction between l-DOPA, d-DOPA, l-tyrosine, or l-phenylalanine and caffeic acid, p-coumaric acid, or cinnamic acid, and compounds 12 and 13 were derived from 1. Among tested compounds 1-13, those containing one or two catechol moieties exhibited potent anti-aggregation

  阿尔茨海默氏病（AD）是一种神经退行性疾病，其特征是淀粉样β蛋白（Aβ）聚集。Aβ通过β折叠形成聚集，并诱导针对神经元细胞的细胞毒性。因此，天然存在的化合物抑制Aβ聚集是治疗AD的有前途的策略。我们已经报道了具有两个或多个邻苯二酚部分的咖啡酰奎尼酸和苯乙酮类糖苷强烈抑制了Aβ聚集。从可可豆（Theobroma cacao L.）分离的含有两个邻苯二酚部分的环丙酰胺（1）被认为对Aβ聚集具有预防作用。为了研究氯丁酰胺（1）抑制Aβ聚集的构效关系，我们通过1-DOPA，d-DOPA，l-酪氨酸，或l-苯丙氨酸和咖啡酸，对香豆酸或肉桂酸，化合物12和13衍生自1。在测试的化合物1-13中，含有一个或两个邻苯二酚部分的化合物表现出强的抗聚集活性，而非儿茶酚类相关化合物几乎没有活性。这表明至少一个儿茶酚部分对于抑制Aβ42聚集是必不可少的，并且该活性根据儿茶酚部分的数目而增加。因此，clovamid
• 一种防治糖尿病和糖尿病肾病药物及其合成 方法和应用
  申请人：西安科技大学

  公开号：CN106242987B

  公开（公告）日：2019-02-22

  本发明公开了一种防治糖尿病和糖尿病肾病药物及其合成方法和应用，该药物为咖啡酸‑苯丙氨酸的衍生物，其结构如式I所示，其中，R1、R2为H、OH、OCH3、OCOCH3、3‑甲基丁‑2‑烯基或异戊烯基；R3为H、CH3、Bn、OCH3、OCOCH3、BnCH2、i‑Pr、t‑Bu或金刚烷基；n为0或1。通过STZ诱导的大鼠糖尿病模型，显示该衍生物能够显著降低糖尿病模型大鼠的血糖，同时对糖尿病肾病模型小鼠有一定的保护作用，证实了该衍生物的降糖作用和肾脏保护的作用，可制备糖尿病及糖尿病肾病的相关药物。
• 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。
• 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.
• PRODUCTS COMPRISING N-PHENYLPROPENOYL AMINO ACID AMIDES AND USES THEREOF
  申请人：Nestec S.A.

  公开号：EP2396083A2

  公开（公告）日：2011-12-21