N-trans-p-coumaroyl-3',4'-dihydroxyphenylethylamine | 105954-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-trans-p-coumaroyl-3',4'-dihydroxyphenylethylamine
• 英文别名: N-cinnamoyldopamine；(E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-phenylprop-2-enamide
• CAS: 105954-99-2；103188-45-0
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: OICMBMJTQCLGNP-VQHVLOKHSA-N

物化性质

• 沸点：
  588.4±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-trans-p-coumaroyl-3',4'-dihydroxyphenylethylamine 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  N-[（E）-3,4-亚甲基二氧基肉桂酰基]多巴胺在固态下的新型[2 + 2]光二聚化。

  摘要：

  [反应：见正文]为了使儿茶酚胺具有光反应性，在无溶剂条件下制备了N-肉桂酰基取代的多巴胺（E）-5a-5c和O，O'-二甲基多巴胺（E）-3a-3c。观察到的一个特别有趣的光反应性是N-[（E）-3,4-亚甲基二氧基肉桂酰基]多巴胺（（E）-5c）的固态反应，它经历了新型的[2 + 2]光二聚化反应，仅产生一种三环产物8。该反应是烯烃固态光加成到苯环的第一个例子。

  DOI：

  10.1021/ol0162419
• 作为产物：
  描述：

  肉桂酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-trans-p-coumaroyl-3',4'-dihydroxyphenylethylamine
  参考文献：
  名称：

  Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-.BETA.-phenethylamine and N-Acyldopamine Derivatives.

  摘要：

  N-反式和N-顺式-阿魏酰基酪胺是从印尼药用植物空心菜（旋花科）中分离得到的体外前列腺素（PG）合成抑制剂。为了阐明结构活性关系，合成了可能由天然存在的肉桂酸和β-苯乙胺组合得到的肉桂酰-β-苯乙胺，并测试了它们对PG合成酶和花生四烯酸5-脂氧合酶的抑制活性。含有儿茶酚基团的化合物，如N-咖啡酰基-β-苯乙胺（CaP），显示出对PG合成酶更高的抑制效果。儿茶酚基团被发现对抑制花生四烯酸5-脂氧合酶至关重要。对浓度依赖性PG生物合成效应的研究表明，CaP在较低浓度范围内增强了PG生物合成，而在较高浓度下抑制了反应。通过纯化的PG内过氧化物合成酶和微粒体PG合成酶研究了CaP对每个反应步骤的影响。CaP抑制了环氧合酶反应，同时增强了氢过氧化物酶反应。从多巴胺和脂肪酸合成了含有儿茶酚和脂溶性基团的N-酰基多巴胺，以测试它们对花生四烯酸5-脂氧合酶的抑制效果。N-亚油酰多巴胺是最活跃的化合物，在我们的测定系统中其IC50值为2.3nM，而作为5-脂氧合酶特异性抑制剂的AA 861的IC50值为8nM。

  DOI：

  10.1248/cpb.40.396

文献信息

• 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.
• N-Caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors
  作者：Serge Michalet、Gilbert Cartier、Bruno David、Anne-Marie Mariotte、Marie-Geneviève Dijoux-franca、Glenn W. Kaatz、Michael Stavri、Simon Gibbons

  DOI：10.1016/j.bmcl.2006.12.059

  日期：2007.3

  As part of an ongoing project to identify plant natural products as efflux pump inhibitors (EPIs), bioassay-guided fractionation of the methanolic extract of Mirabilis jalapa Linn. (Nyetaginaceae) led to the isolation of an active polyphenolic amide: N-trans-feruloyl 4'-O-methyldopamine. This compound showed moderate activity as an EPI against multidrug-resistant (MDR) Staphylococcus aureus overexpressing the multidrug efflux transporter NorA, causing an 8-fold reduction of norfloxacin MIC at 292 mu M (100 mu g/mL). This prompted us to synthesize derivatives in order to provide structure-activity relationships and to access more potent inhibitors. Among the synthetic compounds, some were more active than the natural compound and N-trans-3,4-O-dimethylcaffeoyl tryptamine showed potentiation of norfloxacin in MDR S. aureus comparable to that of the standard reserpine. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationships and effects of phenylpropanoid amides of octopamine and dopamine on tyrosinase inhibition and antioxidation
  作者：Zhengrong Wu、Lifang Zheng、Yang Li、Feng Su、Xiaoxuan Yue、Wei Tang、Xiaoyan Ma、Junyu Nie、Hongyu Li

  DOI：10.1016/j.foodchem.2012.02.152

  日期：2012.9

  Phenylpropanoid amides of octopamine (OA) 1a-1e and dopamine (DA) 2a-2e were synthesised and the structure-activity relationships (SARs) for antioxidant and tyrosinase inhibition activities were analysed. Among synthesised compounds, 2c, which contains two catechol moieties, exhibited the most DPPH radical-scavenging activity (EC50 = 16.2 +/- 2.41 mu M), and id exhibited significant tyrosinase inhibitory activity (IC50 = 5.3 +/- 1.8 mu M). Interestingly, with the same acid moiety, OA derivatives showed more inhibitory effect on tyrosinase than did compounds derived from DA, whereas DA derivatives were found to have higher antioxidant activity than compounds derived from OA. The relationship between their structures and their potencies, demonstrated in the current study, will be useful for the design of optimal agents. (C) 2012 Elsevier Ltd. All rights reserved.
• A Novel [2 + 2] Photodimerization of <i>N</i>-[(<i>E</i>)-3,4-Methylenedioxycinnamoyl]dopamine in the Solid State
  作者：Yoshikatsu Ito、Souta Horie、Yasuhiro Shindo

  DOI：10.1021/ol0162419

  日期：2001.7.1

  [reaction: see text] To give photoreactivity to catecholamines, N-cinnamoyl-substituted dopamines (E)-5a-5c and O,O'-dimethyldopamines (E)-3a-3c were prepared under solvent-free conditions. A particularly interesting observed photoreactivity was that of N-[(E)-3,4-methylenedioxycinnamoyl]dopamine ((E)-5c), which underwent a novel type of [2 + 2] photodimerization in the solid state, giving exclusively

  [反应：见正文]为了使儿茶酚胺具有光反应性，在无溶剂条件下制备了N-肉桂酰基取代的多巴胺（E）-5a-5c和O，O'-二甲基多巴胺（E）-3a-3c。观察到的一个特别有趣的光反应性是N-[（E）-3,4-亚甲基二氧基肉桂酰基]多巴胺（（E）-5c）的固态反应，它经历了新型的[2 + 2]光二聚化反应，仅产生一种三环产物8。该反应是烯烃固态光加成到苯环的第一个例子。
• Inhibition of in Vitro Prostaglandin and Leukotriene Biosyntheses by Cinnamoyl-.BETA.-phenethylamine and N-Acyldopamine Derivatives.
  作者：Chen-Fang TSENG、Satoshi IWAKAMI、Akihiro MIKAJIRI、Masaaki SHIBUYA、Fumio HANAOKA、Yutaka EBIZUKA、Kosashi PADMAWINATA、Ushio SANKAWA

  DOI：10.1248/cpb.40.396

  日期：——

  N-trans- and N-cis-Feruloyltyramines were isolated as the inhibitors of in vitro prostaglandin (PG) synthesis from an Indonesian medicinal plant, Ipomoea aquatica (Convolvulaceae). In order to clarify structure activity relationships, cinnamoyl-β-phenethylamines with possible combinations of naturally occurring cinnamic acids and β-phenethylamines were synthesized and tested for their inhibitory activities against PG synthetase and arachidonate 5-lipoxygenase. The compounds containing catechol groups such as N-caffeoyl-β-phenethylamine (CaP) showed higher inhibitory effects on PG synthetase. The catechol group was found to be essential for the inhibition of arachidonate 5-lipoxygenase. The investigation of concentration dependent effects on PG biosynthesis revealed that CaP enhanced PG biosynthesis at a lower concentration range, whereas it inhibited the reaction at a higher concentration. The effects of CaP on each reaction step were investigated with purified PG endoperoxide synthase and microsomal PG synthetase. CaP inhibited the cyclooxygenase reaction, while it enhanced the hydroperoxidase reaction. N-Acyldopamines which contain catechol and lipophylic group were synthesized from dopamine and fatty acids to test their inhibitory effects on arachidonate 5-lipoxygenase. N-Linoleoyldopamine was the most active compound and its IC50 value was 2.3nM in our assay system, in which an IC50 value of AA 861, a specific inhibitor of 5-lipoxygenase, was 8nM.

  N-反式和N-顺式-阿魏酰基酪胺是从印尼药用植物空心菜（旋花科）中分离得到的体外前列腺素（PG）合成抑制剂。为了阐明结构活性关系，合成了可能由天然存在的肉桂酸和β-苯乙胺组合得到的肉桂酰-β-苯乙胺，并测试了它们对PG合成酶和花生四烯酸5-脂氧合酶的抑制活性。含有儿茶酚基团的化合物，如N-咖啡酰基-β-苯乙胺（CaP），显示出对PG合成酶更高的抑制效果。儿茶酚基团被发现对抑制花生四烯酸5-脂氧合酶至关重要。对浓度依赖性PG生物合成效应的研究表明，CaP在较低浓度范围内增强了PG生物合成，而在较高浓度下抑制了反应。通过纯化的PG内过氧化物合成酶和微粒体PG合成酶研究了CaP对每个反应步骤的影响。CaP抑制了环氧合酶反应，同时增强了氢过氧化物酶反应。从多巴胺和脂肪酸合成了含有儿茶酚和脂溶性基团的N-酰基多巴胺，以测试它们对花生四烯酸5-脂氧合酶的抑制效果。N-亚油酰多巴胺是最活跃的化合物，在我们的测定系统中其IC50值为2.3nM，而作为5-脂氧合酶特异性抑制剂的AA 861的IC50值为8nM。