2'-hydroxy-3,4',5-trimethoxychalcone | 75514-34-0

• 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: 2'-hydroxy-3,4',5-trimethoxychalcone
• 英文别名: 3-(3,5-dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)-2-propen-1-one；2'-hydroxy-3",4',5"-trimethoxychalcone；3-(3,5-Dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• CAS: 75514-34-0
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: RWOYCGABFPHNGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 potassium ferricyanide 、 potassium hydroxide 、 sodium hydroxide 、 肼 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 2'-hydroxy-3,4',5-trimethoxychalcone
  参考文献：
  名称：

  3,5,2′,4′-Tetrahydroxychalcone, a new non-purine xanthine oxidase inhibitor

  摘要：

  Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid and the overproduction of uric acid will lead to hyperuricemia which is an important cause of gout. In the present study, three chalcone derivatives were synthesized and evaluated for inhibitory activity against xanthine oxidase in vitro. Of the compounds, only Compound 1, 3,5,2',4'-tetrahydroxychalcone, exhibited a significant inhibitory activity on xanthine oxidase with an IC50 value of 22.5 mu M. Lineweaver-Burk transformation of the inhibition kinetics data demonstrated that it was a competitive inhibitor of xanthine oxidase and Ki value was 17.4 mu M. In vivo, intragastric administration of Compound 1 was able to significantly reduce serum uric acid levels and inhibited hepatic xanthine oxidase activities of hyperuricemic mice in a dose-dependent manner. Acute toxicity study in mice showed that Compound 1 was very safe at a dose of up to 5 g/kg. These results suggest that Compound 1 is a novel competitive xanthine oxidase inhibitor and is worthy of further development. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.cbi.2010.12.004

文献信息

• Synthesis and complete assignment of NMR data of 20 chalcones
  作者：Doseok Hwang、Jiye Hyun、Geunhyeong Jo、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.2707

  日期：2011.1

  O‐methyltransferases in plant biosynthetic pathways. Assignments of NMR peaks in the spectra of hydroxylated and/or methoxylated chalcones can help in identifying novel chalcone derivatives isolated from natural sources by referencing these data against NMR spectra obtained from known chalcones. We report here the syntheses of 20 chalcones and complete assignments of 1H and 13C NMR spectra. Copyright © 2010 John Wiley

  查耳酮是类黄酮生物合成的中间体，具有抗菌、抗增殖和抗炎特性。查耳酮含有两个苯环，羟基化和甲氧基化的类似物通常由植物生物合成途径中的羟化酶和 O-甲基转移酶产生。羟基化和/或甲氧基化查耳酮光谱中 NMR 峰的归属可以帮助通过将这些数据与从已知查耳酮获得的 NMR 谱相比较来鉴定从天然来源分离的新型查耳酮衍生物。我们在此报告了 20 种查耳酮的合成以及 1H 和 13C NMR 光谱的完整分配。版权所有 © 2010 John Wiley & Sons, Ltd.
• Investigation of Chalcones as Selective Inhibitors of the Breast Cancer Resistance Protein: Critical Role of Methoxylation in both Inhibition Potency and Cytotoxicity
  作者：Glaucio Valdameri、Charlotte Gauthier、Raphaël Terreux、Rémy Kachadourian、Brian J. Day、Sheila M. B. Winnischofer、Maria E. M. Rocha、Véronique Frachet、Xavier Ronot、Attilio Di Pietro、Ahcène Boumendjel

  DOI：10.1021/jm2016528

  日期：2012.4.12

  ABCG2 plays a major role in anticancer-drug efflux and related tumor multidrug resistance. Potent and selective ABCG2 inhibitors with low cytotoxicity were investigated among a series of 44 chalcones and analogues (1,3-diarylpropenones), by evaluating their inhibitory effect on the transport of mitoxantrone, a known ABCG2 substrate. Six compounds producing complete inhibition with IC50 values below 0.5 mu M and high selectivity for ABCG2 were identified. The number and position of methoxy substituents appeared to be critical for both inhibition and cytotoxicity. The best compounds, with potent inhibition and low toxicity, contained an N-methyl-1-indolyl (compound 38) or a 6'-hydroxyl-2',4'-dimethoxy-1-phenyl (compound 27) moiety (A-ring) and two methoxy groups at positions 2 and 6 of the 3-phenyl moiety (B-ring). Methoxy substitution contributed to inhibition at positions 3 and 5, but had a negative effect at position 4. Finally, methoxy groups at positions 3, 4, and 5 of the B-ring markedly increased cytotoxicity and, therefore, should be avoided.