(E)-2-phenyl-N-pyrazin-2-yl-3-thiophen-2-ylacrylamide | 1046150-79-1

• 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: (E)-2-phenyl-N-pyrazin-2-yl-3-thiophen-2-ylacrylamide
• 英文别名: (E)-2-phenyl-N-(pyrazin-2-yl)-3-(thiophen-2-yl)acrylamide；(E)-2-phenyl-N-pyrazin-2-yl-3-thiophen-2-ylprop-2-enamide
• CAS: 1046150-79-1
• 化学式: C₁₇H₁₃N₃OS
• 分子量: 307.376
• InChiKey: VQHRYNOCPAXJQV-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氨基吡嗪 、 E-3-(2-thienyl)-2-phenylacrylic acid 在 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以7%的产率得到(E)-2-phenyl-N-pyrazin-2-yl-3-thiophen-2-ylacrylamide
  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

文献信息

• SAR, Pharmacokinetics, Safety, and Efficacy of Glucokinase Activating 2-(4-Sulfonylphenyl)-<i>N</i>-thiazol-2-ylacetamides: Discovery of PSN-GK1
  作者：Lisa S. Bertram、Daniel Black、Paul H. Briner、Rosemary Chatfield、Andrew Cooke、Matthew C. T. Fyfe、P. John Murray、Frédéric Naud、Masao Nawano、Martin J. Procter、Günaj Rakipovski、Chrystelle M. Rasamison、Christine Reynet、Karen L. Schofield、Vilas K. Shah、Felix Spindler、Amanda Taylor、Roy Turton、Geoffrey M. Williams、Philippe Wong-Kai-In、Kosuke Yasuda

  DOI：10.1021/jm8003202

  日期：2008.7.1

  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.