4-(2,5-dimethoxy-phenylazo)-resorcinol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-(2,5-dimethoxy-phenylazo)-resorcinol
• 英文别名: 4-(2,5-Dimethoxy-phenylazo)-resorcin
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: UYPYULYCVXPIPY-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  83.64
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基苯甲酸 在 盐酸 、 叠氮磷酸二苯酯 、 三乙胺 、 苯甲酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 4-(2,5-dimethoxy-phenylazo)-resorcinol
  参考文献：
  名称：

  Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors

  摘要：

  Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 mu M, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC50 value of IC50 = 36.28 +/- 0.72 mu M, comparable to that of resveratrol, a well-known tyrosinase inhibitor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.050

文献信息

• Takahashi, Nippon Kagaku Zasshi, <hi>1953</hi>, vol. 74, p. 673
  作者：Takahashi

  DOI：——

  日期：——
• Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors
  作者：Yu Min Song、Young Mi Ha、Jin-Ah Kim、Ki Wung Chung、Yohei Uehara、Kyung Jin Lee、Pusoon Chun、Youngjoo Byun、Hae Young Chung、Hyung Ryong Moon

  DOI：10.1016/j.bmcl.2012.10.050

  日期：2012.12

  Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 mu M, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC50 value of IC50 = 36.28 +/- 0.72 mu M, comparable to that of resveratrol, a well-known tyrosinase inhibitor. (C) 2012 Elsevier Ltd. All rights reserved.