(E)-2-cyano-3-(2,4-dimethoxyphenyl)acrylamide

• 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: (E)-2-cyano-3-(2,4-dimethoxyphenyl)acrylamide
• 英文别名: 2-Cyano-3-(2,4-dimethoxyphenyl)prop-2-enamide；(E)-2-cyano-3-(2,4-dimethoxyphenyl)prop-2-enamide
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: WPPQGZFEWZSGOX-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-二甲氧基苯甲醛 、 氰乙酰胺 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以91.4%的产率得到(E)-2-cyano-3-(2,4-dimethoxyphenyl)acrylamide
  参考文献：
  名称：

  (E)-2-Cyano-3-(substituted phenyl)acrylamide analogs as potent inhibitors of tyrosinase: A linear β-phenyl-α,β-unsaturated carbonyl scaffold

  摘要：

  In this study, we synthesized (E)-2-cyano-3-(substituted phenyl) acrylamide (CPA) derivatives which possess a linear beta-phenyl-alpha,beta-unsaturated carbonyl scaffold and examined their inhibitory activities against tyrosinase. CPA analogs exerted inhibitory activity against mushroom tyrosinase. Results from the docking simulation indicated that CPA2 could bind directly to the active site of mushroom tyrosinase and the binding affinity of CPA2 for tyrosinase might be higher than that of kojic acid, a well-known potent tyrosinase inhibitor. In B16F10 cells, CPA2 significantly suppressed tyrosinase activity and melanogenesis in a dose-dependent manner. At the concentration of 25 mu M, CPA2 exhibited tyrosinase inhibitory activity comparable to that of kojic acid with no cytotoxic effect. Results from the present study suggest that CPA2 bearing a linear beta-phenyl-alpha,beta-unsaturated carbonyl scaffold may be the potential candidate for treatment of diseases associated with hyperpigmentation and that a linear beta-phenyl-alpha,beta-unsaturated carbonyl scaffold might be closely related to potent tyrosinase inhibition. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.015

文献信息

• Triflic acid-catalyzed metal-free synthesis of (<i>E</i>)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones
  作者：Bapurao D. Rupanwar、Santosh S. Chavan、Anil M. Shelke、Gurunath M. Suryavanshi

  DOI：10.1039/c7nj05169g

  日期：——

  efficient synthesis of biologically active (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones has been reported with 64–94% yields under metal-free conditions. The reaction proceeds through sequential Knoevenagel condensation/stereoselective in situ monohydration of nitrile or C–N cyclization protocol in one-pot. The attractive features of this tandem process are moderate reaction conditions

  据报道，在无金属条件下，TfOH催化可高效合成具有生物活性的（E）-2-氰基丙烯酰胺和3-取代的氮杂环丁烷2,4-二酮，收率为64-94％。反应通过一锅顺序进行的Knoevenagel缩合反应/腈选择性地原位单水合或CN环化方案进行。该串联方法的吸引人的特征是中等反应条件，高原子经济性，广泛的底物范围，克级反应和易于操作。