4,2',4'-trihydroxy-3-methoxychalcone | 21583-31-3

• 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: 4,2',4'-trihydroxy-3-methoxychalcone
• 英文别名: 4,2',4'-Trihydroxy-3-methoxy-chalkon；1-(2,4-Dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one；1-(2,4-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one
• CAS: 21583-31-3
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: BWFSBUVPIAIXKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C(Solv: benzene (71-43-2))
• 沸点：
  523.8±50.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,2',4'-trihydroxy-3-methoxychalcone 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以22%的产率得到4-[5-(4-hydroxy-3-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]benzene-1,3-diol
  参考文献：
  名称：

  Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors

  摘要：

  In this study, twenty 3,5-diaryl-4,5-dihydro-1H-pyrazole derivatives with hydroxyl(s) (1a-1p, 2a-2d) were synthesized and their inhibitory activity on mushroom tyrosinase was examined. The results showed that among these compounds, 1-(5-(3,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone 1d was found to be the most potent tyrosinase inhibitor with IC50 value of 0.301 mu M. Kinetic study revealed that these compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.12.054
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 香草醛 在 sodium hydroxide 作用下， 生成 4,2',4'-trihydroxy-3-methoxychalcone
  参考文献：
  名称：

  Glycolytic Inhibition and Antidiabetic Activity on Synthesized Flavanone Scaffolds with Computer Aided Drug Designing Tools

  摘要：

  背景：糖尿病是一种具有挑战性的代谢紊乱，当HbA1c水平未得到控制时会导致一系列并发症。市场上现有的大部分长期使用的药物可能会导致严重的不良反应。因此，当前的研究重点在于通过合成天然模拟类黄酮类似物来开发治疗糖尿病的药物。 目标：本研究侧重于合成模拟天然类黄酮核心的黄酮衍生物，并对其抗糖尿病和抗氧化活性进行研究，这有助于开发针对糖尿病管理的药物发现。 材料和方法：从1,3-二苯基-丙-2-烯-1-酮衍生物合成了新型的2-苯基-2,3-二氢-香豆素，并利用紫外线、红外线、核磁共振、质谱等技术对其进行表征。通过图论分析确定了药物靶点位点，并通过对其物理化学性质、ADMET研究和分子对接分析进行了体外研究。通过体外（α-淀粉酶抑制实验）和体内模型研究了抗糖尿病和自由基清除效果。利用链脲霉素（STZ）诱导的大鼠作为体内模型。 结果：α-淀粉酶抑制实验显示，具有羟基取代的黄酮类物质HFA1-HFA7具有显著的IC50值。将试验化合物（HFA3-HFA7）以40 mg/kg剂量用于STZ诱导的大鼠，发现HFA5、HFA4和HFA6等具有电子给予基团（如羟基、甲氧基和硫苯基）的化合物明显恢复了血糖水平和抗氧化酶活性，与格列本脲相比。 结论：这些结果表明，天然模拟合成的黄酮类物质具有抗糖尿病和抗氧化性能，有助于开发针对糖尿病管理的药物。

  DOI：

  10.2174/1570180817999201209204523

文献信息

• Pyrazoline-based mycobactin analogues as MAO-inhibitors
  作者：Venkatesan Jayaprakash、Barij N. Sinha、Gulberk Ucar、Ayse Ercan

  DOI：10.1016/j.bmcl.2008.10.084

  日期：2008.12

  3,5-Diaryl carbothioamide pyrazolines designed as mycobactin analogs (mycobacterial siderophore) were reported to be potent antitubercular agents under iron limiting condition in our earlier study. Clinical complications of newly introduced antibiotic Linezolid, due its MAO inhibitory activity, prompted us to evaluate our compounds for their MAO-inhibitory activity against rat liver MAO-A and MAO-B as pyrazolines were reported to be antidepressants and MAO inhibitors. The present study carried out with this pilot library of 32 compounds will provide us with necessary information for designing antitubercular molecules with reduced MAO-inhibitory activity and also help us in identifying a selective MAO-B inhibitor which has potential clinical utility in neurodegenerative disorders. Thirty-two compounds analyzed has shown spectrum of activity from selective to nonselective against two isoforms of rat liver MAO-A and MAO-B and also as competitive, reversible to non-competitive, irreversible. It is also interesting to note that anti-tubercular compound 11, 14 and 16 were also found to be selective inhibitors of rat liver MAO-B. Docking studies with human MAO shows that compound 11 interacts with the catalytic site of both the isoforms, suggesting compound 11 as nonselective inhibitor of human MAO isoforms. (C) 2008 Elsevier Ltd. All rights reserved.
• Self-developed NF-κB inhibitor 270 protects against LPS-induced acute kidney injury and lung injury through improving inflammation
  作者：Yan-yan Yu、Xiang-qian Li、Wen-peng Hu、Shi-chao Cu、Jia-jia Dai、Ya-nan Gao、Yi-ting Zhang、Xiao-yi Bai、Da-yong Shi

  DOI：10.1016/j.biopha.2022.112615

  日期：2022.3