N-[(2E)-3-(3,4-二羟基苯基)-2-丙烯酰基]酪氨酸 | 124027-56-1

• 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
• 中文名称: N-[(2E)-3-(3,4-二羟基苯基)-2-丙烯酰基]酪氨酸
• 中文别名: 3,7-二羟基-7-乙基胆烷酸
• 英文名称: caffeoyl tyrosine
• 英文别名: (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine；caffeoyl-N-tyrosine；N-(E)-Caffeoyl-L-tyrosine；(2S)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
• CAS: 124027-56-1
• 化学式: C₁₈H₁₇NO₆
• 分子量: 343.336
• InChiKey: JRXLVUMFJASLDR-PXYYCUNGSA-N

物化性质

• 沸点：
  726.4±60.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 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：
  127
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(2E)-3-(3,4-二羟基苯基)-2-丙烯酰基]酪氨酸 生成 L-酪氨酸盐酸盐
  参考文献：
  名称：

  CLIFFORD, MICHAEL N.;KELLARD, BRIAN;AH-SING, ERIC, PHYTOCHEMISTRY, 28,(1989) N, C. 1989-1990

  摘要：

  DOI：
• 作为产物：
  描述：

  TRANS-咖啡酸 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.33h， 生成 N-[(2E)-3-(3,4-二羟基苯基)-2-丙烯酰基]酪氨酸
  参考文献：
  名称：

  Isolation, Structure Determination, Synthesis, and Sensory Activity of N-Phenylpropenoyl-l-amino Acids from Cocoa (Theobroma cacao)

  摘要：

  Application of chromatographic separation and taste dilution analyses recently revealed besides procyanidins a series of N-phenylpropenoyl amino acids as the key contributors to the astringent taste of nonfermented cocoa beans as well as roasted cocoa nibs. Because these amides have as yet not been reported as key taste compounds, this paper presents the isolation, structure determination, and sensory activity of these amino acid amides. Besides the previously reported (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine (clovamide), (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-tyrosine (deoxyclovamide), and (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-tyrosine, seven additional amides, namely, (+)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-aspartic acid, (+)-N-[4'-hydroxy-(E)-cinnamoyl]-L-aspartic acid, (-)-N-[3',4'-dihydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-L-glutamic acid, (-)-N-[4'-hydroxy-(E)-cinnamoyl]-3-hydroxy-L-tyrosine, (+)-N-[4'-hydroxy-3'-methoxy-(E)-cinnamoyl]-L-aspartic acid, and (+)-N-[(E)-cinnamoyl]-L-aspartic acid, were identified for the first time in cocoa products by means of LC-MS/MS, 1D/2D-NMR, UV-vis, CID spectroscopy, and polarimetry, as well as independent enantiopure synthesis. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying oral sensation were determined to be between 26 and 220 mu mol/L (water) depending on the amino acid moiety. In addition, exposure to light rapidly converted these [E]-configured N-phenylpropenoyl amino acids into the corresponding [2]-isomers, thus indicating that analysis of these compounds in food and plant materials needs to be performed very carefully in the absence of light to prevent artifact formation.

  DOI：

  10.1021/jf050458q

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
• 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。
• 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。
• Derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition
  申请人：——

  公开号：US20040082664A1

  公开（公告）日：2004-04-29

  The present invention relates to derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition, more particularly the compounds of the present invention specifically inhibit the activation of T lymphocyte by src homology region 2(SH2) domain of T lymphocyte (lck), so that they can be used for the treatment, prevention and/or diagnosis of graft rejection, autoimmune diseases, inflammatory diseases, etc.

  本发明涉及羟基苯基衍生物、其制备方法及其药物组合物，更具体地，本发明的化合物特异性地抑制T淋巴细胞的src同源区域2（SH2）结构域（lck），从而可用于移植排斥、自身免疫性疾病、炎症性疾病等的治疗、预防和/或诊断。
• Synthesis and evaluation of inhibitors of Mycobacterium tuberculosis UGM using bioisosteric replacement
  作者：Jian Fu、Ziyao He、Huixiao Fu、Yufen Xia、Inès N'Go、Huayong Lou、Jinglan Wu、Weidong Pan、Stéphane P. Vincent

  DOI：10.1016/j.bmc.2022.116896

  日期：2022.9

  study, we report on the synthesis of amides derived from rosmarinic acid, their inhibitory effect towards purified UGM using three distinct biochemical assays: FP, HPLC and SPR. The rosmarinic amides generally showed a significantly higher affinity for UGM than the corresponding rosmarinic ester. In particular, compound 5h displayed interesting binding affinity values (Kd = 58 ± 7, 63 ± 9 µM towards

  由于耐药结核病的出现，目前的治疗方法不足，因此缺乏结核病 (TB) 药物开发活动。酶 UDP-吡喃半乳糖变位酶 (UGM) 参与半乳聚糖的生物合成，这对细胞壁完整性和细菌活力至关重要。因此，它的抑制被认为是抗结核药物发现的有利可图的策略。在这项研究中，我们报告了从迷迭香酸衍生的酰胺的合成，它们使用三种不同的生化测定法对纯化的 UGM 的抑制作用：FP、HPLC 和 SPR。与相应的迷迭香酸酯相比，迷迭香酰胺通常对UGM显示出显着更高的亲和力。特别是，化合物5 h显示出有趣的结合亲和力值 ( Kd  = 58 ± 7, 63 ± 9 µM 分别朝向Kp UGM 和Mt UGM）。此外，建立了一种新的 UGM SPR 测定，并证实5小时与 UGM 结合，解离常数为 104.8 ± 6.5 μM。总的来说，这项研究验证了酰胺生物等排策略，该策略已成功实施以从迷迭香酸开发 UGM 抑制剂，为进一步设计新型