(E)-3-(3-bromo-4-hydroxyphenyl)-2-cyanoacrylamide

• 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)-3-(3-bromo-4-hydroxyphenyl)-2-cyanoacrylamide
• 英文别名: (E)-3-(3-bromo-4-hydroxyphenyl)-2-cyanoprop-2-enamide
• 化学式: C₁₀H₇BrN₂O₂
• 分子量: 267.082
• InChiKey: GCZFJXDLMHAZOM-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-4-羟基苯甲醛 、 氰乙酰胺 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以64.2%的产率得到(E)-3-(3-bromo-4-hydroxyphenyl)-2-cyanoacrylamide
  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

• (E)-2-Cyano-3-(substituted phenyl)acrylamide analogs as potent inhibitors of tyrosinase: A linear β-phenyl-α,β-unsaturated carbonyl scaffold
  作者：Sujin Son、Haewon Kim、Hwi Young Yun、Do Hyun Kim、Sultan Ullah、Seong Jin Kim、Yeon-Jeong Kim、Min-Soo Kim、Jin-Wook Yoo、Pusoon Chun、Hyung Ryong Moon

  DOI：10.1016/j.bmc.2015.11.015

  日期：2015.12

  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.