(S)-benzyl 3-cyclopentyl-2-(4-(isopropylsulfonyl)-2-oxopyridin-1(2H)-yl)propanoate | 1152511-11-9

• 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: (S)-benzyl 3-cyclopentyl-2-(4-(isopropylsulfonyl)-2-oxopyridin-1(2H)-yl)propanoate
• 英文别名: benzyl (2S)-3-cyclopentyl-2-(2-oxo-4-propan-2-ylsulfonylpyridin-1-yl)propanoate
• CAS: 1152511-11-9
• 化学式: C₂₃H₂₉NO₅S
• 分子量: 431.553
• InChiKey: VTTHUUULBYOFLV-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  (S)-benzyl 3-cyclopentyl-2-(4-(isopropylsulfonyl)-2-oxopyridin-1(2H)-yl)propanoate 、 2-氨基-5-三氟甲基吡啶 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)-3-cyclopentyl-2-(4-(isopropylsulfonyl)-2-oxopyridin-1(2H)-yl)-N-(5-(trifluoromethyl)pyridin-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 水 为溶剂， 生成 (S)-benzyl 3-cyclopentyl-2-(4-(isopropylsulfonyl)-2-oxopyridin-1(2H)-yl)propanoate
  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

文献信息

• Novel and efficient synthesis of 4-sulfonyl-2-pyridones
  作者：Martha L. Minich、Isa D. Watson、Kevin J. Filipski、Jeffrey A. Pfefferkorn

  DOI：10.1016/j.tetlet.2009.02.120

  日期：2009.5

  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.