N-[4'-hydroxy-(E)-cinnamoyl]-L-tryptophan methyl ester | 1418029-47-6

• 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
• 英文名称: N-[4'-hydroxy-(E)-cinnamoyl]-L-tryptophan methyl ester
• 英文别名: N-[4′-hydroxy-(E)-cinnamoyl]-L-tryptophan methyl ester；p-coumaroyltryptophan methyl ester；methyl (2S)-2-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 1418029-47-6
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: KXANVARYXQCGJU-BLRBJFNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[4'-hydroxy-(E)-cinnamoyl]-L-tryptophan methyl ester 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以91%的产率得到p-coumaroyl-N-tryptophan
  参考文献：
  名称：

  Hydroxycinnamoyl Amino Acids Conjugates: A Chiral Pool to Distinguish Commercially Exploited Coffea spp.

  摘要：

  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。

  DOI：

  10.3390/molecules25071704
• 作为产物：
  描述：

  4-香豆酸 、 L-色氨酸甲酯 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 72.0h， 以72%的产率得到N-[4'-hydroxy-(E)-cinnamoyl]-L-tryptophan methyl ester
  参考文献：
  名称：

  Hydroxycinnamoyl Amino Acids Conjugates: A Chiral Pool to Distinguish Commercially Exploited Coffea spp.

  摘要：

  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。

  DOI：

  10.3390/molecules25071704

文献信息

• Javamide-I-O-methyl ester increases p53 acetylation and induces cell death via activating caspase 3/7 in monocytic THP-1 cells
  作者：Jae B. Park

  DOI：10.1016/j.phymed.2016.10.004

  日期：2016.12

  Previous study suggested that javamide-II may be a potent compound with Sirt1/2 inhibition activity. PURPOSE However, the effects of javamide-I and the its O-methyl ester on Sirt inhibition, p53 acetylation and cell death have not been investigated. METHODS The isolation and synthesis of javamide-I and its O-methyl ester analogue were confirmed by NMR. Their potential effects on Sirt1/2/3, p53 acetylation

  背景技术Javamide-I和-II是在Coffea sp。中发现的酚酰胺化合物。先前的研究表明，javamide-II可能是具有Sirt1 / 2抑制活性的有效化合物。目的然而，尚未研究javamide-I及其O-甲基酯对Sirt抑制，p53乙酰化和细胞死亡的影响。方法NMR证实了Javamide-I及其邻甲基酯类似物的分离与合成。使用sirt分析，计算机模拟分析，Western印迹，caspase 3/7和凋亡分析方法检查了它们对Sirt1 / 2/3，p53乙酰化和细胞死亡的潜在影响。结果Javamide-I及其O-甲酯显示出相似的抑制模式。Sirt1（IC50为19µM）优于Sirt2（IC50为104µM）和Sirt3（IC50为160µM）。然而，发现javamide-I及其O-甲基酯比Sirt2更好地抑制Sirt1，这不同于javamide-II能够比Sirt1更强地抑制Si
• In Silico Screening and In Vitro Activity Measurement of Javamide Analogues as Potential p38 MAPK Inhibitors
  作者：Jae Park

  DOI：10.3390/ijms18122704

  日期：——

  inhibit p38 MAPK, the treatment of javamide-II-ethyl and -methyl esters could suppress the production of IL-8 and MCP-1 protein significantly by 22-73% (p < 0.05) in the differentiated THP-1 cells, and the inhibition was slightly stronger by the ethyl ester than the methyl ester. Altogether, this study suggests that javamide-II-O-ethyl ester may be a most potent p38 MAPK inhibitor among the tested compounds

  p38丝裂原激活的蛋白激酶（p38 MAPK）是一种关键的蛋白激酶，与炎症/应激相关疾病的进展密切相关。我们的数据表明，javamide类似物可能具有很强的抗炎活性，但有关其对p38 MAPK的影响的信息很少。因此，在本文中，使用计算机筛选和体外p38 MAPK测定方法研究了三十种javamide类似物对p38 MAPK的影响。合成了javamide类似物，并使用核磁共振（NMR）光谱法确定了其化学结构。然后，使用计算机模拟程序筛选javamide类似物。筛选出的类似物表现出广泛的结合能（ΔE； -20至-39）和几种具有ΔE的类似物。-34至-39显示出与p38 MAPK的强结合亲和力。在体外p38 MAPK分析中，该激酶被具有高结合能（ΔE; -34至-39）和计算机模拟评分（Avg。评分; -27.5至-29.3）的类似物显着抑制。此外，两种检测方法的比较分析显示计算机模拟评分与p38
• Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides
  作者：Lyubomir Georgiev、Maya Chochkova、Iskra Totseva、Katya Seizova、Emma Marinova、Galya Ivanova、Mariana Ninova、Hristo Najdenski、Tsenka Milkova

  DOI：10.1007/s00044-012-0419-x

  日期：2013.9

  Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.
• 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。