2-Fluoro-5-(propane-2-sulfonyl)benzoic acid | 1152548-25-8

• 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: 2-Fluoro-5-(propane-2-sulfonyl)benzoic acid
• 英文别名: 2-fluoro-5-propan-2-ylsulfonylbenzoic acid
• CAS: 1152548-25-8
• 化学式: C₁₀H₁₁FO₄S
• mdl: MFCD11103050
• 分子量: 246.259
• InChiKey: KKKNTSIWQQISLN-UHFFFAOYSA-N

物化性质

• 沸点：
  436.3±45.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Fluoro-5-(propane-2-sulfonyl)benzoic acid 在 caesium carbonate 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-phenyl-5-[5-(propane-2-sulfonyl)-2-{[(2S)-1,1,1-trifluoropropan-2-yl]oxy}benzoyl]-2H,4H,5H,6H-pyrrolo[3,4-c]pyrazole
  参考文献：
  名称：

  Design and Synthesis of Novel and Selective Glycine Transporter-1 (GlyT1) Inhibitors with Memory Enhancing Properties

  摘要：

  We report here the identification and optimization of a novel series of potent GlyT1 inhibitors. A ligand design campaign that utilized known GlyT1 inhibitors as starting points led to the identification of a novel series of pyrrolo[3,4-c]pyrazoles amides (21-50) with good in vitro potency. Subsequent optimization of physicochemical and in vitro ADME properties produced several compounds with promising pharmacokinetic profiles. In vivo inhibition of GlyT1 was demonstrated for select compounds within this series by measuring the elevation of glycine in the cerebro-spinal fluid (CSF) of rats after a single oral dose of 10 mg/kg. Ultimately, an optimized lead, compound 46, demonstrated in vivo efficacy in a rat novel object recognition (NOR) assay after oral dosing at 0.1, 1, and 3 mg/kg.

  DOI：

  10.1021/acs.jmedchem.8b00372