5,5-diethoxy-3-(ethylsulfonyl)pent-2-enoic acid | 1152510-73-0

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: 5,5-diethoxy-3-(ethylsulfonyl)pent-2-enoic acid
• 英文别名: 5,5-Diethoxy-3-ethylsulfonylpent-2-enoic acid
• CAS: 1152510-73-0
• 化学式: C₁₁H₂₀O₆S
• 分子量: 280.342
• InChiKey: NJLMBAHNUZHMOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  98.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5-diethoxy-3-(ethylsulfonyl)pent-2-enoic acid 、 benzyl (2S)-2-amino-3-(oxan-4-yl)propanoate 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  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：

  ethyl 5,5-diethoxy-3-(ethylsulfonyl)pent-2-enoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 5,5-diethoxy-3-(ethylsulfonyl)pent-2-enoic acid
  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.