(S)-benzyl 2-(4-(cyclobutylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate | 1152511-13-1

• 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: (S)-benzyl 2-(4-(cyclobutylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate
• 英文别名: benzyl (2S)-2-(4-cyclobutylsulfonyl-2-oxopyridin-1-yl)-3-cyclopentylpropanoate
• CAS: 1152511-13-1
• 化学式: C₂₄H₂₉NO₅S
• 分子量: 443.564
• InChiKey: KKPYRJPQHSFCOW-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氨基吡嗪 、 (S)-benzyl 2-(4-(cyclobutylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate 在 三甲基铝 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 (S)-2-(4-(cyclobutylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentyl-N-(pyrazin-2-yl)propanamide
  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：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以380 mg的产率得到(S)-benzyl 2-(4-(cyclobutylsulfonyl)-2-oxopyridin-1(2H)-yl)-3-cyclopentylpropanoate
  参考文献：
  名称：

  Novel and efficient synthesis of 4-sulfonyl-2-pyridones

  摘要：

  Heterocyclic 4-sulfonyl-2-pyridones represent useful scaffolds for drug discovery and are also versatile synthetic building blocks. Herein we describe a novel and efficient synthesis of this heterocyclic ring system utilizing an acid mediated cyclo-condensation reaction. This synthetic method affords convenient access to structurally diverse N-substituted 4-sulfonyl-2-pyridones in moderate to good yields. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.120