N-2-hydroxy-2-(4-hydroxyphenyl)ethyl cinnamide

• 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-2-hydroxy-2-(4-hydroxyphenyl)ethyl cinnamide
• 英文别名: (E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-phenylprop-2-enamide
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: CWMOJJSULWWJSO-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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-2-hydroxy-2-(4-hydroxyphenyl)ethyl cinnamide 在 三溴化磷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Metabolic activation of aegeline mediated by CYP2C19

  摘要：

  DOI：

  10.1080/00498254.2021.1913666
• 作为产物：
  描述：

  苯甲醛 在 哌啶 、 吡啶 、 (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-2-hydroxy-2-(4-hydroxyphenyl)ethyl cinnamide
  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

• Some alkaloids from aegle marmelos
  作者：Tuticorin R. Govindachari、Manakkal S. Premila

  DOI：10.1016/s0031-9422(00)86977-0

  日期：1983.1
• 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.
• Metabolic activation of aegeline mediated by CYP2C19
  作者：Min Tian、Shenzhi Zhou、Wei Li、Jiaru Li、Lan Yang、Ying Peng、Jiang Zheng

  DOI：10.1080/00498254.2021.1913666

  日期：2021.11.2