3,4-dimethoxy,2',4',6'-trihydroxychalcone | 25515-48-4

• 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: 3,4-dimethoxy,2',4',6'-trihydroxychalcone
• 英文别名: (E)-3-(3,4-dimethoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 25515-48-4
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: FSUQQYNYAWWMTD-HWKANZROSA-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：

  2,4,6-三羟基苯乙酮一水合物 在 盐酸 、 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 26.5h， 生成 3,4-dimethoxy,2',4',6'-trihydroxychalcone
  参考文献：
  名称：

  Synthesis and evaluation of antiplatelet activity of trihydroxychalcone derivatives

  摘要：

  In an effort to develop potent antiplatelet agents, a series of trihydroxychalcones was synthesized and screened in vitro for their inhibitory effects on washed rabbit platelet aggregation induced by arachidonic acid (100 mu M) and collagen (10 eta g/ml). Of five compounds with potent inhibitory effects on arachidonic acid- and collagen-induced platelet aggregation, compound 4e was found to be the most potent. The structure-activity relationships suggested that antiplatelet activity was governed to a greater extent by the substituent on B ring of the chalcone template, and most of the active compounds had methoxy or dimethoxy groups on B ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.039

文献信息

• Photorearrangement of phenyl cinnamates under micellar environment
  作者：A.K. Singh、T.S. Raghuraman

  DOI：10.1016/s0040-4039(00)89310-7

  日期：1985.1

  Photolysis of phenyl cinnamates in aqueous SDS medium results in an efficient and high yield synthesis of the corresponding 2′-hydroxychalcones.

  肉桂酸苯基酯在水性SDS介质中的光解作用可有效且高产率地合成相应的2'-羟基查耳酮。
• 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.
• Synthesis and evaluation of antiplatelet activity of trihydroxychalcone derivatives
  作者：Li-Ming Zhao、Hai-Shan Jin、Liang-Peng Sun、Hu-Ri Piao、Zhe-Shan Quan

  DOI：10.1016/j.bmcl.2005.08.039

  日期：2005.11

  In an effort to develop potent antiplatelet agents, a series of trihydroxychalcones was synthesized and screened in vitro for their inhibitory effects on washed rabbit platelet aggregation induced by arachidonic acid (100 mu M) and collagen (10 eta g/ml). Of five compounds with potent inhibitory effects on arachidonic acid- and collagen-induced platelet aggregation, compound 4e was found to be the most potent. The structure-activity relationships suggested that antiplatelet activity was governed to a greater extent by the substituent on B ring of the chalcone template, and most of the active compounds had methoxy or dimethoxy groups on B ring. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 2,4,6-Trihydroxychalcone Derivatives as Novel Protein Tyrosine Phosphatase 1B Inhibitors
  作者：Liang-Peng Sun、Li-Xin Gao、Wei-Ping Ma、Fa-Jun Nan、Jia Li、Hu-Ri Piao

  DOI：10.1111/j.1747-0285.2012.01431.x

  日期：2012.10

  A series of 2,4,6‐trihydroxychalcone derivatives were synthesized and identified as reversible and competitive protein tyrosine phosphatase (PTP) 1B inhibitors with IC50 values in the micromolar range. Compound 4a had the greatest in vitro inhibition activity against PTP1B (IC50 = 0.27 ± 0.01 μm) and the best selectivity (6.9‐fold) for PTP1B relative to T‐cell protein tyrosine phosphatases. The compounds identified herein provide a foundation on which to design specific inhibitors of PTP1B and other PTPs.