(4-环戊基硫烷基苯基)乙酸 | 1046150-88-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: (4-环戊基硫烷基苯基)乙酸
• 英文名称: (4-cyclopentylsulfanylphenyl)acetic acid
• 英文别名: 2-(4-Cyclopentylsulfanylphenyl)acetic acid
• CAS: 1046150-88-2
• 化学式: C₁₃H₁₆O₂S
• 分子量: 236.335
• InChiKey: LHAYITWZIJDAHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-环戊基硫烷基苯基)乙酸 、 左旋伪麻黄碱 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到2-(4-cyclopentylsulfanylphenyl)-N-((1R,2R)-2-hydroxy-1-methyl-2-phenylethyl)-N-methylacetamide
  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 (4-cyclopentylsulfanylphenyl)acetate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以95%的产率得到(4-环戊基硫烷基苯基)乙酸
  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.