ethyl 6-phenoxy-2-oxo-2H-1-benzopyran-3-carboxylate | 946137-34-4

• 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: ethyl 6-phenoxy-2-oxo-2H-1-benzopyran-3-carboxylate
• 英文别名: Ethyl 2-oxo-6-phenoxychromene-3-carboxylate
• CAS: 946137-34-4
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: WCTRKLLFLSTUKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-phenoxy-2-oxo-2H-1-benzopyran-3-carboxylate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Mechanism-Based Thrombin Inhibitors:  Design, Synthesis, and Molecular Docking of a New Selective 2-Oxo-2H-1-benzopyran Derivative

  摘要：

  New 2-oxo-2H-1-benzopyran derivatives were prepared to optimize 2a,b, initially developed as mechanism-based alpha-chymotrypsin (alpha-CT) inhibitors, into potent and selective thrombin (THR) inhibitors. From this study, 22, characterized by a 2-(N-ethyl-2'-oxoacetamide)-5'-chlorophenyl ester side chain, was shown to be a good THR inhibitor (k(i)/K-I = 3455 M-1 center dot s(-1)), displaying an excellent selectivity profile against other serine proteases such as factor Xa, trypsin, and alpha-CT. Docking analysis of this compound into the different protein structures revealed the molecular basis responsible for its potency and selectivity.

  DOI：

  10.1021/jm061368v
• 作为产物：
  描述：

  4-苯氧基苯酚 在 哌啶 、 sodium hydroxide 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 ethyl 6-phenoxy-2-oxo-2H-1-benzopyran-3-carboxylate
  参考文献：
  名称：

  Mechanism-Based Thrombin Inhibitors:  Design, Synthesis, and Molecular Docking of a New Selective 2-Oxo-2H-1-benzopyran Derivative

  摘要：

  New 2-oxo-2H-1-benzopyran derivatives were prepared to optimize 2a,b, initially developed as mechanism-based alpha-chymotrypsin (alpha-CT) inhibitors, into potent and selective thrombin (THR) inhibitors. From this study, 22, characterized by a 2-(N-ethyl-2'-oxoacetamide)-5'-chlorophenyl ester side chain, was shown to be a good THR inhibitor (k(i)/K-I = 3455 M-1 center dot s(-1)), displaying an excellent selectivity profile against other serine proteases such as factor Xa, trypsin, and alpha-CT. Docking analysis of this compound into the different protein structures revealed the molecular basis responsible for its potency and selectivity.

  DOI：

  10.1021/jm061368v

文献信息

• Mechanism-Based Thrombin Inhibitors:  Design, Synthesis, and Molecular Docking of a New Selective 2-Oxo-2<i>H</i>-1-benzopyran Derivative
  作者：Raphaël Frédérick、Séverine Robert、Caroline Charlier、Johan Wouters、Bernard Masereel、Lionel Pochet

  DOI：10.1021/jm061368v

  日期：2007.7.1

  New 2-oxo-2H-1-benzopyran derivatives were prepared to optimize 2a,b, initially developed as mechanism-based alpha-chymotrypsin (alpha-CT) inhibitors, into potent and selective thrombin (THR) inhibitors. From this study, 22, characterized by a 2-(N-ethyl-2'-oxoacetamide)-5'-chlorophenyl ester side chain, was shown to be a good THR inhibitor (k(i)/K-I = 3455 M-1 center dot s(-1)), displaying an excellent selectivity profile against other serine proteases such as factor Xa, trypsin, and alpha-CT. Docking analysis of this compound into the different protein structures revealed the molecular basis responsible for its potency and selectivity.