2'-hydroxy-2,4',6'-trimethoxychalcone | 118267-80-4

• 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: 2'-hydroxy-2,4',6'-trimethoxychalcone
• 英文别名: 1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• CAS: 118267-80-4
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: KKTYCZKXENFEJP-UHFFFAOYSA-N

物化性质

• 熔点：
  171-173 °C
• 沸点：
  529.9±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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

• 作为反应物：
  描述：

  2'-hydroxy-2,4',6'-trimethoxychalcone 在 mercury(II) diacetate 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 2',4,6-trimethoxyaurone
  参考文献：
  名称：

  Aurones as histone deacetylase inhibitors: Identification of key features

  摘要：

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.019
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 、 邻甲氧基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 51.0h， 生成 2'-hydroxy-2,4',6'-trimethoxychalcone
  参考文献：
  名称：

  Flavokawains B和C，黑色素生成抑制剂，从胡椒胡椒的根中分离出来，并合成类似物

  摘要：

  发现胡椒的根的乙醇提取物抑制了MSH激活的B16黑色素瘤细胞中的黑色素生成。基于它们的抗黑素生成活性，从该提取物中分离出黄酮类固醇B和C，发现抑制黑素生成的IC 50值分别为7.7μM和6.9μM 。Flavokawain类似物是通过其相应的苯乙酮和苯甲醛的Claisen-Schmidt缩合反应合成的，并根据其酪氨酸酶抑制和抗黑色素生成活性进行了评估。在使用MSH激活的B16黑色素瘤细胞的黑色素生成抑制试验中，化合物1b最有效，IC 50值为2.3μM。

  DOI：

  10.1016/j.bmcl.2014.12.082

文献信息

• 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.