ethyl 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylate
• 英文别名: Ethyl 2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enoate；ethyl 2-(4-methylsulfonylphenyl)-3-(oxan-4-yl)prop-2-enoate
• 化学式: C₁₇H₂₂O₅S
• 分子量: 338.425
• InChiKey: OLCZVCWNOGDQFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以71 g的产率得到(E)-2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylic acid
  参考文献：
  名称：

  SAR, Pharmacokinetics, Safety, and Efficacy of Glucokinase Activating 2-(4-Sulfonylphenyl)-N-thiazol-2-ylacetamides: Discovery of PSN-GK1

  摘要：

  Allosteric activators of the glucose-sensing enzyme glucokinase (GK) are currently attracting much interest as potential antidiabetic therapies because they can achieve powerful blood glucose lowering through actions in multiple organs. Here, the optimization of a weakly active high-throughput screening hit to (2R)-2-(4-cyclopropanesulfonylphenyl)-N-(5-fluorothiazol-2-yl)-3-(tetrahydropyran-4-yl)propionamide (PSN-GK1), a potent GK activator with an improved pharmacokinetic and safety profile, is described. Following oral administration, this compound elicited robust glucose lowering in rats.

  DOI：

  10.1021/jm8003202
• 作为产物：
  描述：

  ethyl 2-(4-methylsulfanylphenyl)-3-(tetrahydropyran-4-yl)acrylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)acrylate
  参考文献：
  名称：

  SAR, Pharmacokinetics, Safety, and Efficacy of Glucokinase Activating 2-(4-Sulfonylphenyl)-N-thiazol-2-ylacetamides: Discovery of PSN-GK1

  摘要：

  Allosteric activators of the glucose-sensing enzyme glucokinase (GK) are currently attracting much interest as potential antidiabetic therapies because they can achieve powerful blood glucose lowering through actions in multiple organs. Here, the optimization of a weakly active high-throughput screening hit to (2R)-2-(4-cyclopropanesulfonylphenyl)-N-(5-fluorothiazol-2-yl)-3-(tetrahydropyran-4-yl)propionamide (PSN-GK1), a potent GK activator with an improved pharmacokinetic and safety profile, is described. Following oral administration, this compound elicited robust glucose lowering in rats.

  DOI：

  10.1021/jm8003202