3,4-dimethyl-7-{[(2E)-3-phenylprop-2-en-1-yl]oxy}-2H-chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3,4-dimethyl-7-{[(2E)-3-phenylprop-2-en-1-yl]oxy}-2H-chromen-2-one
• 英文别名: 3,4-dimethyl-7-[(E)-3-phenylprop-2-enoxy]chromen-2-one
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: JSZCZPUJFPDZEI-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  二甲基伞形酮 、 Cinnamyl bromide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到3,4-dimethyl-7-{[(2E)-3-phenylprop-2-en-1-yl]oxy}-2H-chromen-2-one
  参考文献：
  名称：

  Structural Insights into Monoamine Oxidase Inhibitory Potency and Selectivity of 7-Substituted Coumarins from Ligand- and Target-Based Approaches

  摘要：

  A new series of 3-, 4-, 7-polysubstituted coumarins have been designed and evaluated for their monoamine oxidase A and monoamine oxidase B (MAO-A and MAO-B) inhibitory potency. Substituents at position 7 consisted of a bridge of different physicochemical nature linking a phenyl ring to the coumarin scaffold. Structure-affinity and structure-selectivity relationships, derived through CoMFA-GOLPE and docking studies, revealed the key physicochemical interactions responsible for the observed MAO-B and MAO-A inhibitory potency and suggested the main structural determinants for high selectivity toward one of the two enzymatic isoforms. The predictive power of our models was proved with the design of a new inhibitor demonstrating an outstanding MAO-B affinity (pIC(50) = 8.29) and the highest MAO-B selectivity (Delta pIC(50) = 3.39) within the entire series of ligands examined herein.

  DOI：

  10.1021/jm060183l

文献信息

• Structural Insights into Monoamine Oxidase Inhibitory Potency and Selectivity of 7-Substituted Coumarins from Ligand- and Target-Based Approaches
  作者：Marco Catto、Orazio Nicolotti、Francesco Leonetti、Andrea Carotti、Angelo Danilo Favia、Ramón Soto-Otero、Estefanía Méndez-Álvarez、Angelo Carotti

  DOI：10.1021/jm060183l

  日期：2006.8.1

  A new series of 3-, 4-, 7-polysubstituted coumarins have been designed and evaluated for their monoamine oxidase A and monoamine oxidase B (MAO-A and MAO-B) inhibitory potency. Substituents at position 7 consisted of a bridge of different physicochemical nature linking a phenyl ring to the coumarin scaffold. Structure-affinity and structure-selectivity relationships, derived through CoMFA-GOLPE and docking studies, revealed the key physicochemical interactions responsible for the observed MAO-B and MAO-A inhibitory potency and suggested the main structural determinants for high selectivity toward one of the two enzymatic isoforms. The predictive power of our models was proved with the design of a new inhibitor demonstrating an outstanding MAO-B affinity (pIC(50) = 8.29) and the highest MAO-B selectivity (Delta pIC(50) = 3.39) within the entire series of ligands examined herein.