(E)-3-(2,4-dihydroxyphenyl)-1-(2,4,6- trihydroxyphenyl)prop-2-en-1-one | 29287-25-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(2,4-dihydroxyphenyl)-1-(2,4,6- trihydroxyphenyl)prop-2-en-1-one
• 英文别名: 2,2',4,4',6'-Pentahydroxychalcone；(E)-3-(2,4-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 29287-25-0
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: MDRJIGPMMMALHB-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 盐酸 、 氢氧化钾 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 36.67h， 生成 (E)-3-(2,4-dihydroxyphenyl)-1-(2,4,6- trihydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and evaluation of 2′,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors

  摘要：

  In this study, we synthesized a series of hydroxychalcones and examined their tyrosinase inhibitory activity. The results showed that 2',4',6'-trihydroxychalcone (1), 2,2',3,4',6'-pentahydroxychalcone (4), 2',3,4,4,5,6'-hexahydroxychalcone (5), 2',4',6'-trihydroxy- 3,4-dimethoxychalcone (9) and 2,2,4,4',6'-pentahydroxychalcone (15) exhibited high inhibitory effects on tyrosinase with respect to L-tyrosine as a substrate. By the structure activity relationship study, it was suggested that the 2',4',6'-trihydroxyl substructure in the chalcone skeleton were efficacious for the inhibition of tyrosinase activity. And also, the catechol structure on B-ring of chalcones was not advantageous for the inhibitory potency. Furthermore, 15 (IC50 = 1 mu M) was found to show the highest activity out of a set of 15 hydroxychalcones, even better than both 2,2',4,4'-tetrahydroxychalcone (13, IC50 = 5 mu M) and kojic acid (16, IC50 = 12 mu M), which were known as potent tyrosinase inhibitors. Kinetic study revealed that 15 acts as a competitive inhibitor of tyrosinase with K-i value of 3.1 mu M. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.017

文献信息

• Synthesis and evaluation of 2′,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors
  作者：Nishida Jun、Gao Hong、Kawabata Jun

  DOI：10.1016/j.bmc.2007.01.017

  日期：2007.3

  In this study, we synthesized a series of hydroxychalcones and examined their tyrosinase inhibitory activity. The results showed that 2',4',6'-trihydroxychalcone (1), 2,2',3,4',6'-pentahydroxychalcone (4), 2',3,4,4,5,6'-hexahydroxychalcone (5), 2',4',6'-trihydroxy- 3,4-dimethoxychalcone (9) and 2,2,4,4',6'-pentahydroxychalcone (15) exhibited high inhibitory effects on tyrosinase with respect to L-tyrosine as a substrate. By the structure activity relationship study, it was suggested that the 2',4',6'-trihydroxyl substructure in the chalcone skeleton were efficacious for the inhibition of tyrosinase activity. And also, the catechol structure on B-ring of chalcones was not advantageous for the inhibitory potency. Furthermore, 15 (IC50 = 1 mu M) was found to show the highest activity out of a set of 15 hydroxychalcones, even better than both 2,2',4,4'-tetrahydroxychalcone (13, IC50 = 5 mu M) and kojic acid (16, IC50 = 12 mu M), which were known as potent tyrosinase inhibitors. Kinetic study revealed that 15 acts as a competitive inhibitor of tyrosinase with K-i value of 3.1 mu M. (c) 2007 Elsevier Ltd. All rights reserved.