N-(2-((5-(trifluoromethyl)pyridin-2-yl)sulfonyl)ethyl)-1-naphthamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-((5-(trifluoromethyl)pyridin-2-yl)sulfonyl)ethyl)-1-naphthamide
• 英文别名: N-[2-[5-(trifluoromethyl)pyridin-2-yl]sulfonylethyl]naphthalene-1-carboxamide
• 化学式: C₁₉H₁₅F₃N₂O₃S
• 分子量: 408.401
• InChiKey: QEFCWXOPGISNKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-巯基-5-(三氟甲基)吡啶 在 盐酸 、 Oxone 、 potassium phosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 68.0h， 生成 N-(2-((5-(trifluoromethyl)pyridin-2-yl)sulfonyl)ethyl)-1-naphthamide
  参考文献：
  名称：

  Synthesis of 5-trifluoromethyl-2-sulfonylpyridine PPARβ/δ antagonists: Effects on the affinity and selectivity towards PPARβ/δ

  摘要：

  The covalent modification of peroxisome-proliferator activated receptor beta/delta (PPAR beta/delta) is part of the mode of action of 5-trifluoromethyl-2-sulfonylpyridine PPAR beta/delta antagonists such as GSK3787 and CC618. Herein, the synthesis and in vitro biological evaluation of a range of structural analogues of the two antagonists are reported. The new ligands demonstrate that an improvement in the selectivity of 5-trifluoromethyl-2-sulfonylpyridine antagonists towards PPAR beta/delta is achievable at the expense of their immediate affinity for PPAR beta/delta. However, their putatively covalent and irreversible mode of action may ensure their efficacy over time, as observed in time-resolved fluorescence resonance energy transfer (TR-FRET)-based ligand displacement assays. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.012

文献信息

• Synthesis of 5-trifluoromethyl-2-sulfonylpyridine PPARβ/δ antagonists: Effects on the affinity and selectivity towards PPARβ/δ
  作者：Åsmund Kaupang、Eili Tranheim Kase、Cecilie Xuan Trang Vo、Marthe Amundsen、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.bmc.2015.12.012

  日期：2016.1

  The covalent modification of peroxisome-proliferator activated receptor beta/delta (PPAR beta/delta) is part of the mode of action of 5-trifluoromethyl-2-sulfonylpyridine PPAR beta/delta antagonists such as GSK3787 and CC618. Herein, the synthesis and in vitro biological evaluation of a range of structural analogues of the two antagonists are reported. The new ligands demonstrate that an improvement in the selectivity of 5-trifluoromethyl-2-sulfonylpyridine antagonists towards PPAR beta/delta is achievable at the expense of their immediate affinity for PPAR beta/delta. However, their putatively covalent and irreversible mode of action may ensure their efficacy over time, as observed in time-resolved fluorescence resonance energy transfer (TR-FRET)-based ligand displacement assays. (c) 2015 Elsevier Ltd. All rights reserved.