N-Sinapoyldopamine | 220957-88-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-Sinapoyldopamine
• 英文别名: (E)-N-[2-(3,4-dihydroxyphenyl)ethyl]-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamide
• CAS: 220957-88-0
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: IHPKYZSMSPBNQE-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  多巴胺 、 3,5-二甲氧基-4-羟基肉桂酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-Sinapoyldopamine
  参考文献：
  名称：

  Synthesis and structure–activity relationships and effects of phenylpropanoid amides of octopamine and dopamine on tyrosinase inhibition and antioxidation

  摘要：

  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.

  DOI：

  10.1016/j.foodchem.2012.02.152

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.
• 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.