2',3,4-trihydroxy-4',6'-dimethoxychalcone

• 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: 2',3,4-trihydroxy-4',6'-dimethoxychalcone
• 英文别名: 2',3,4-trihydroxy-4',6'-dimethoxychalchone；(E)-3-(3,4-dihydroxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: OLHMLJHXCUWPOE-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 在 盐酸 、 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 72.75h， 生成 2',3,4-trihydroxy-4',6'-dimethoxychalcone
  参考文献：
  名称：

  DPPH Radical Scavenging Reaction of Hydroxy- and Methoxychalcones

  摘要：

  在酒精和非酒精溶剂中，对带有 2,3- 和 3,4- 二羟基以及 3,4,5- 三羟基 B 环的 2′,4′,6′-三羟基和 2′-羟基-4′,6′-二甲氧基查耳酮的 DPPH 自由基清除活性进行了评估。所有测试化合物都能清除两个当量以上的自由基，并可能转化为相应的 B 环醌，在大多数情况下还会环化为醛酮和黄酮，这些化合物在反应溶液中通过原位核磁共振分析得以确定。有趣的是，2′,3,4-三羟基-4′,6′-二甲氧基查尔酮与 DPPH 自由基的反应受到所用溶剂的显著影响，这可能是由于环化为醛酮的准备程度不同造成的。

  DOI：

  10.1271/bbb.70.193

文献信息

• DPPH Radical Scavenging Reaction of Hydroxy- and Methoxychalcones
  作者：Jun NISHIDA、Jun KAWABATA

  DOI：10.1271/bbb.70.193

  日期：2006.1

  The DPPH radical scavenging activity of 2′,4′,6′-trihydroxy- and 2′-hydroxy-4′,6′-dimethoxychalcones carrying a 2,3- and 3,4-dihydroxylated, and 3,4,5-trihydroxylated B-ring was evaluated in alcoholic and non-alcoholic solvents. All test compounds scavenged more than two equivalent of radicals by a possible conversion to the corresponding B-ring quinones and in most cases subsequently underwent cyclization to aurones and flavanones, these being identified in the reaction solutions by an in situ NMR analysis. Interestingly, the reaction between 2′,3,4-trihydroxy-4′,6′-dimethoxychalcone and the DPPH radical was significantly affected by the solvent used, which might be accounted for by the difference in readiness for cyclization to an aurone.

  在酒精和非酒精溶剂中，对带有 2,3- 和 3,4- 二羟基以及 3,4,5- 三羟基 B 环的 2′,4′,6′-三羟基和 2′-羟基-4′,6′-二甲氧基查耳酮的 DPPH 自由基清除活性进行了评估。所有测试化合物都能清除两个当量以上的自由基，并可能转化为相应的 B 环醌，在大多数情况下还会环化为醛酮和黄酮，这些化合物在反应溶液中通过原位核磁共振分析得以确定。有趣的是，2′,3,4-三羟基-4′,6′-二甲氧基查尔酮与 DPPH 自由基的反应受到所用溶剂的显著影响，这可能是由于环化为醛酮的准备程度不同造成的。
• Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship
  作者：Muhammad Nadeem Akhtar、Nurshafika M. Sakeh、Seema Zareen、Sana Gul、Kong Mun Lo、Zaheer Ul-Haq、Syed Adnan Ali Shah、Syahida Ahmad

  DOI：10.1016/j.molstruc.2014.12.073

  日期：2015.4

  Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC50 14.20-14.38 mu M values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discover of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry. (C) 2014 Elsevier B.V. All rights reserved.
• 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.