methyl (S)-2-(5-chloro-4-(methylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate | 1174013-28-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (S)-2-(5-chloro-4-(methylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate
• CAS: 1174013-28-5
• 化学式: C₁₅H₂₀ClNO₅S
• 分子量: 361.846
• InChiKey: JFECBKJFPOFVAH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  82.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-氨基-5-氯吡啶 、 methyl (S)-2-(5-chloro-4-(methylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate 在 二甲基氯化铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 (S)-2-(5-chloro-4-(methylsulfonyl)-2-oxopyridin-1(2H)-yl)-N-(5-chloropyridin-2-yl)-3-cyclopentylpropanamide
  参考文献：
  名称：

  Pyridones as glucokinase activators: Identification of a unique metabolic liability of the 4-sulfonyl-2-pyridone heterocycle

  摘要：

  A promising area of novel anti-diabetic therapy involves identification of small molecule activators of the glucokinase enzyme to reduce blood glucose and normalize glucose stimulated insulin secretion. Herein, we report the identification and optimization of a series of 4-sulfonyl-2-pyridone activators. The activators were evaluated for in vitro biochemical activation and pharmacokinetic properties. As part of these efforts, a unique metabolic liability of the 4-sulfonyl-2-pyridone ring system was identified wherein this heterocycle readily undergoes conjugation with glutathione under non-enzymatic conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.107
• 作为产物：
  描述：

  C₁₅H₂₀ClNO₃S 在 oxone 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以71%的产率得到methyl (S)-2-(5-chloro-4-(methylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate
  参考文献：
  名称：

  Pyridones as glucokinase activators: Identification of a unique metabolic liability of the 4-sulfonyl-2-pyridone heterocycle

  摘要：

  A promising area of novel anti-diabetic therapy involves identification of small molecule activators of the glucokinase enzyme to reduce blood glucose and normalize glucose stimulated insulin secretion. Herein, we report the identification and optimization of a series of 4-sulfonyl-2-pyridone activators. The activators were evaluated for in vitro biochemical activation and pharmacokinetic properties. As part of these efforts, a unique metabolic liability of the 4-sulfonyl-2-pyridone ring system was identified wherein this heterocycle readily undergoes conjugation with glutathione under non-enzymatic conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.107