7-(3-benzoyloxy-4-fluorobenzyloxy)-3,4-dimethyl-2H-chromen-2-one | 320350-99-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 7-(3-benzoyloxy-4-fluorobenzyloxy)-3,4-dimethyl-2H-chromen-2-one
• CAS: 320350-99-0
• 化学式: C₂₅H₁₉FO₅
• 分子量: 418.421
• InChiKey: PYJLKSVQAJURGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-(3-benzoyloxy-4-fluorobenzyloxy)-3,4-dimethyl-2H-chromen-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 7-(4-Fluoro-3-hydroxy-benzyloxy)-3,4-dimethyl-chromen-2-one
  参考文献：
  名称：

  Inhibition of Monoamine Oxidases by Functionalized Coumarin Derivatives:  Biological Activities, QSARs, and 3D-QSARs

  摘要：

  A large series of coumarin derivatives (71 compounds) were tested for their monoamine oxidase A and B (MAO-A and MAO-B) inhibitory activity. Most of the compounds acted preferentially on MAO-B with IC50 values in the micromolar to low-nanomolar range; high inhibitory activities toward MAO-A were also measured for sulfonic acid esters. The most active compound was 7-[(3,4-difluorobenzyl)oxy]-3,4-dimethylcoumarin, with an IC50 value toward MAO-B of 1.14 nM. A QSAR study of 7-X-benzyloxy meta-substituted 3,4-dimethylcoumarin derivatives acting on MAO-B yielded good statistical results (q(2) = 0.72, r(2) = 0.86), revealing the importance of lipophilic interactions in modulating the inhibition and excluding any dependence on electronic properties. CoMFA was performed on two data sets of MAO-A and MAO-B inhibitors. The GOLPE procedure, with variable selection criteria, was applied to improve the predictivity of the models and to facilitate the graphical interpretation of results.

  DOI：

  10.1021/jm001028o
• 作为产物：
  描述：

  2-氟-5-甲基苯酚 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 8.75h， 生成 7-(3-benzoyloxy-4-fluorobenzyloxy)-3,4-dimethyl-2H-chromen-2-one
  参考文献：
  名称：

  Inhibition of Monoamine Oxidases by Functionalized Coumarin Derivatives:  Biological Activities, QSARs, and 3D-QSARs

  摘要：

  A large series of coumarin derivatives (71 compounds) were tested for their monoamine oxidase A and B (MAO-A and MAO-B) inhibitory activity. Most of the compounds acted preferentially on MAO-B with IC50 values in the micromolar to low-nanomolar range; high inhibitory activities toward MAO-A were also measured for sulfonic acid esters. The most active compound was 7-[(3,4-difluorobenzyl)oxy]-3,4-dimethylcoumarin, with an IC50 value toward MAO-B of 1.14 nM. A QSAR study of 7-X-benzyloxy meta-substituted 3,4-dimethylcoumarin derivatives acting on MAO-B yielded good statistical results (q(2) = 0.72, r(2) = 0.86), revealing the importance of lipophilic interactions in modulating the inhibition and excluding any dependence on electronic properties. CoMFA was performed on two data sets of MAO-A and MAO-B inhibitors. The GOLPE procedure, with variable selection criteria, was applied to improve the predictivity of the models and to facilitate the graphical interpretation of results.

  DOI：

  10.1021/jm001028o