8-ethoxy-3-p-tolyl-2H-chromen-2-one | 1367782-56-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 8-ethoxy-3-p-tolyl-2H-chromen-2-one
• 英文别名: 8-Ethoxy-3-(4-methylphenyl)chromen-2-one；8-ethoxy-3-(4-methylphenyl)chromen-2-one
• CAS: 1367782-56-6
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: LRTCGXDWWJVNBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 8-ethoxy-3-p-tolyl-2H-chromen-2-one
  参考文献：
  名称：

  3-苯基香豆素衍生物的合成及镇痛和抗氧化活性评价

  摘要：

  由取代芳香醛与苯乙酸反应制备的一系列3-苯基取代香豆素衍生物。通过FT-IR、1H NMR谱和元素分析证实了取代香豆素衍生物的化学组成。设计的 3-苯基香豆素衍生物与环氧合酶-2 (COX-2) 酶（PDB 代码：3Q7D）对接。合成化合物并根据最高结合亲和力评估其体内镇痛和体外抗氧化活性。化合物02、10和11表现出显着的镇痛活性。与抗坏血酸相比，化合物09、04、01和03在DPPH方法中显示出显着的抗氧化潜力，化合物05和07在一氧化氮清除方法中显示出优异的清除潜力。这项研究工作包括3-苯基香豆素支架的合成及其镇痛和抗氧化活性的评估。

  DOI：

  10.14233/ajchem.2023.28059

文献信息

• Structure-Based Optimization of Coumarin hA₃ Adenosine Receptor Antagonists
  作者：Maria João Matos、Santiago Vilar、Saleta Vazquez-Rodriguez、Sonja Kachler、Karl-Norbert Klotz、Michela Buccioni、Giovanna Delogu、Lourdes Santana、Eugenio Uriarte、Fernanda Borges

  DOI：10.1021/acs.jmedchem.9b01572

  日期：2020.3.12

  Adenosine receptors participate in many physiological functions. Molecules that may selectively interact with one of the receptors are favorable multifunctional chemical entities to treat or decelerate the evolution of different diseases. 3-Arylcoumarins have already been studied as neuroprotective agents by our group. Here, differently 8-substituted 3-arylcoumarins are complementarily studied as ligands of adenosine receptors, performing radioligand binding assays. Among the synthesized compounds, selective A(3) receptor antagonists were found. 3-(4-Bromophenyl)-8-hydroxycoumarin (compound 4) displayed the highest potency and selectivity as A(3) receptor antagonist (K-i = 258 nM). An analysis of its X-ray diffraction provided detailed information on its structure. Further evaluation of a selected series of compounds indicated that it is the nature and position of the substituents that determine their activity and selectivity. Theoretical modeling calculations corroborate and explain the experimental data, suggesting this novel scaffold can be involved in the generation of candidates as multitarget drugs.
• Synthesis and Evaluation of Analgesic and Antioxidant Activity of 3-Phenyl Coumarin Derivatives
  作者：PRAJAKTA ADSULE、Dishank Purandare、S. KULKARNI、R. JOSHI、A. CHABUKSWAR

  DOI：10.14233/ajchem.2023.28059

  日期：——

  the highest binding affinity. Compounds 02, 10, and 11 exhibited significant analgesic activity. Compounds 09, 04, 01, and 03 showed significant antioxidant potential in the DPPH method, and Compounds 05 and 07 have shown excellent scavenging potential in the nitric oxide scavenging method compared to ascorbic acid. This research work includes the synthesis of 3-phenyl coumarin scaffolds and the evaluation

  由取代芳香醛与苯乙酸反应制备的一系列3-苯基取代香豆素衍生物。通过FT-IR、1H NMR谱和元素分析证实了取代香豆素衍生物的化学组成。设计的 3-苯基香豆素衍生物与环氧合酶-2 (COX-2) 酶（PDB 代码：3Q7D）对接。合成化合物并根据最高结合亲和力评估其体内镇痛和体外抗氧化活性。化合物02、10和11表现出显着的镇痛活性。与抗坏血酸相比，化合物09、04、01和03在DPPH方法中显示出显着的抗氧化潜力，化合物05和07在一氧化氮清除方法中显示出优异的清除潜力。这项研究工作包括3-苯基香豆素支架的合成及其镇痛和抗氧化活性的评估。