8-methoxy-3-(4'-methylphenyl)coumarin

• 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-methoxy-3-(4'-methylphenyl)coumarin
• 英文别名: 8-Methoxy-3-(4-methylphenyl)chromen-2-one
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: UVXVVLCFJBJNAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methoxy-3-(4'-methylphenyl)coumarin 在 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 反应 3.0h， 生成 8-hydroxy-3-(4-methylphenyl)-coumarin
  参考文献：
  名称：

  Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins

  摘要：

  In the present work we synthesized a series of hydroxy-3-arylcoumarins (compounds 1-9), some of them previously described as MAO-B selective inhibitors, with the aim of evaluating their antioxidant properties. Theoretical evaluation of ADME properties of all the derivatives was also carried. out. From the ORAC-FL, ESR and CV data it was concluded that these derivatives are very good antioxidants, with a very interesting hydroxyl, DPPH and superoxide radicals scavenging profiles. In particular compound 9 is the most active and effective antioxidant of the series (ORAC-FL = 13.5, capacity of scavenging hydroxyl radicals = 100%, capacity of scavenging DPPH radicals = 65.9% and capacity of scavenging superoxide radicals = 71.5%). Kinetics profile for protection fluorescein probe against peroxyl radicals by addition of antioxidant molecule 9 was also performed. Therefore, it can operate as a potential candidate for preventing or minimizing the free radicals overproduction in oxidative-stress related diseases. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.015
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以70.1 %的产率得到8-methoxy-3-(4'-methylphenyl)coumarin
  参考文献：
  名称：

  Synthesis, Molecular Modeling and Cytotoxicity Study of New 3-Phenyl Coumarin Derivatives against in vitro Cell Lines

  摘要：

  In pursuit of more effective cancer treatments, researchers embarked on a study to enhance the coumarin derivative’s therapeutic potential. These compounds, known for their anticancer properties, have faced challenges such as increased toxicity and drug resistance. The research aimed to design, synthesize and assess new 3-phenyl coumarin derivatives specifically for breast and lung cancer treatment. Utilizing 3-oxoacyl-reductase (1T8I), a series of compounds were synthesized from aromatic aldehydes and phenylacetic acid. Among the synthesized 11 compounds that were examined, compounds C01, C04, C05 and C08 had significant cytotoxic effects on both MCF-7 and MRC-5 cell lines. Particularly, compound C08, featuring ethoxy and nitrate substitution, exhibited remarkable potential against both cancer cell lines, emphasizing its promise for further exploration in cancer therapy.

  DOI：

  10.14233/ajchem.2024.31269

文献信息

• A Convenient Synthesis Of 3-Arylcoumarins From Arylacetonitriles
  作者：C. Mhiri、F. Ladhar、R. El Gharbi、Y. Le Bigot

  DOI：10.1080/00397919908086125

  日期：1999.5

  The condensation of salicylaldehydes with various arylacetonitriles catalyzed by anion-exchange resins such as Amberlite IRA 900, leads to the corresponding 3-arylcoumarins in good yields and selectivity.
• Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins
  作者：Maria João Matos、Fernanda Pérez-Cruz、Saleta Vazquez-Rodriguez、Eugenio Uriarte、Lourdes Santana、Fernanda Borges、Claudio Olea-Azar

  DOI：10.1016/j.bmc.2013.04.015

  日期：2013.7

  In the present work we synthesized a series of hydroxy-3-arylcoumarins (compounds 1-9), some of them previously described as MAO-B selective inhibitors, with the aim of evaluating their antioxidant properties. Theoretical evaluation of ADME properties of all the derivatives was also carried. out. From the ORAC-FL, ESR and CV data it was concluded that these derivatives are very good antioxidants, with a very interesting hydroxyl, DPPH and superoxide radicals scavenging profiles. In particular compound 9 is the most active and effective antioxidant of the series (ORAC-FL = 13.5, capacity of scavenging hydroxyl radicals = 100%, capacity of scavenging DPPH radicals = 65.9% and capacity of scavenging superoxide radicals = 71.5%). Kinetics profile for protection fluorescein probe against peroxyl radicals by addition of antioxidant molecule 9 was also performed. Therefore, it can operate as a potential candidate for preventing or minimizing the free radicals overproduction in oxidative-stress related diseases. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• Synthesis, Molecular Modeling and Cytotoxicity Study of New 3-Phenyl Coumarin Derivatives against in vitro Cell Lines
  作者：Anuruddha Chabukswar、Prajakta V. Adsule、Swati Jagdale、Dishank V. Purandare、Kunal Raut、Yash Kale

  DOI：10.14233/ajchem.2024.31269

  日期：——

  In pursuit of more effective cancer treatments, researchers embarked on a study to enhance the coumarin derivative’s therapeutic potential. These compounds, known for their anticancer properties, have faced challenges such as increased toxicity and drug resistance. The research aimed to design, synthesize and assess new 3-phenyl coumarin derivatives specifically for breast and lung cancer treatment. Utilizing 3-oxoacyl-reductase (1T8I), a series of compounds were synthesized from aromatic aldehydes and phenylacetic acid. Among the synthesized 11 compounds that were examined, compounds C01, C04, C05 and C08 had significant cytotoxic effects on both MCF-7 and MRC-5 cell lines. Particularly, compound C08, featuring ethoxy and nitrate substitution, exhibited remarkable potential against both cancer cell lines, emphasizing its promise for further exploration in cancer therapy.