tert-butyl (2-((5-(trifluoromethyl)pyridin-2-yl)thio)ethyl)carbamate | 1207192-84-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tert-butyl (2-((5-(trifluoromethyl)pyridin-2-yl)thio)ethyl)carbamate
• 英文别名: 1,1-dimethylethyl (2-{[5-(trifluoromethyl)-2-pyridyl]thio}ethyl)carbamate；[2-(5-Trifluoromethyl-pyridin-2-ylsulfanyl)-ethyl]-carbamic acid tert-butyl ester；tert-butyl N-[2-[5-(trifluoromethyl)pyridin-2-yl]sulfanylethyl]carbamate
• CAS: 1207192-84-4
• 化学式: C₁₃H₁₇F₃N₂O₂S
• 分子量: 322.351
• InChiKey: ZHZMSXUHARHCJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  76.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2-((5-(trifluoromethyl)pyridin-2-yl)thio)ethyl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到2-((5-(trifluoromethyl)pyridin-2-yl)thio)ethanaminium chloride
  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
• 作为产物：
  描述：

  N-Boc-溴乙胺 、 2-巯基-5-(三氟甲基)吡啶 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 tert-butyl (2-((5-(trifluoromethyl)pyridin-2-yl)thio)ethyl)carbamate
  参考文献：
  名称：

  Identification and Characterization of 4-Chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide (GSK3787), a Selective and Irreversible Peroxisome Proliferator-Activated Receptor δ (PPARδ) Antagonist

  摘要：

  4-Chloro-N-(2-{[5-trifluoromethyl)-2-pyridyl]sulfonyl}ethyl)benzamide 3 (GSK3787) was identified as a potent and selective ligand for PPAR delta wish good pharmacokinetic properties. A detailed binding study using mass spectral analysis confirmed covalent binding to Cys249 within the PPAR delta binding pocket. Gene expression studies showed that pyridylsulfone 3 antagonized the transcriptional activity of PPAR delta and inhibited basal CPT1a gene transcription. Compound 3 is a PPAR delta antagonist with utility as it tool to elucidate PPAR delta cell biology and pharmacology.

  DOI：

  10.1021/jm900464j