1-[5-(4-amino-2,6-dichlorophenoxy)pyridin-3-yl]ethanone | 1422348-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[5-(4-amino-2,6-dichlorophenoxy)pyridin-3-yl]ethanone
• CAS: 1422348-25-1
• 化学式: C₁₃H₁₀Cl₂N₂O₂
• 分子量: 297.141
• InChiKey: RKVPMVZQNNTZKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.21
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[5-(4-amino-2,6-dichlorophenoxy)pyridin-3-yl]ethanone 、 2,4-二氯苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-[4-(5-acetylpyridin-3-yl)oxy-3,5-dichlorophenyl]-2,4-dichlorobenzenesulfonamide
  参考文献：
  名称：

  Discovery of INT131: A selective PPARγ modulator that enhances insulin sensitivity

  摘要：

  PPAR gamma is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPAR gamma modulators (SPPAR gamma Ms) and display a unique pharmacological profile compared to the thiazolidinedione (TZD) class of PPAR gamma full agonists. Herein we report the initial discovery of partial agonist 4 and the structure-activity relationship studies that led to the selection of clinical compound INT131 (3), a potent PPAR gamma partial agonist that displays robust glucose-lowering activity in rodent models of diabetes while exhibiting a reduced side-effects profile compared to marketed TZDs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.058
• 作为产物：
  描述：

  在 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-[5-(4-amino-2,6-dichlorophenoxy)pyridin-3-yl]ethanone
  参考文献：
  名称：

  Discovery of INT131: A selective PPARγ modulator that enhances insulin sensitivity

  摘要：

  PPAR gamma is a member of the nuclear hormone receptor family and plays a key role in the regulation of glucose homeostasis. This Letter describes the discovery of a novel chemical class of diarylsulfonamide partial agonists that act as selective PPAR gamma modulators (SPPAR gamma Ms) and display a unique pharmacological profile compared to the thiazolidinedione (TZD) class of PPAR gamma full agonists. Herein we report the initial discovery of partial agonist 4 and the structure-activity relationship studies that led to the selection of clinical compound INT131 (3), a potent PPAR gamma partial agonist that displays robust glucose-lowering activity in rodent models of diabetes while exhibiting a reduced side-effects profile compared to marketed TZDs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.058