2-[4-Bromo-2-(3-fluoro-phenylsulfanyl)-phenoxy]-ethanol | 917598-02-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[4-Bromo-2-(3-fluoro-phenylsulfanyl)-phenoxy]-ethanol
• CAS: 917598-02-8
• 化学式: C₁₄H₁₂BrFO₂S
• 分子量: 343.216
• InChiKey: ORZMLSZRDIZCKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[4-Bromo-2-(3-fluoro-phenylsulfanyl)-phenoxy]-ethanol 在 bis-triphenylphosphine-palladium(II) chloride 、 三氟甲磺酸酐 、 potassium carbonate 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 (S)-1-{2-[3-(3-Fluoro-phenylsulfanyl)-biphenyl-4-yloxy]-ethyl}-pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  The synthesis and SAR of 2-arylsulfanylphenyl-1-oxyalkylamino acids as GlyT-1 inhibitors

  摘要：

  Elevation of glycine levels by inhibition of the glycine transporter-1 (GlyT-1) and activation of the NMDA receptor is a potential strategy for the treatment of schizophrenia. A novel series of 2-arylsulfanylphenyl-1-oxyalkyl amino acids have been identified. The most prominent member of this series S-1-{2-[3-(3-fluoro-phenylsulfanyl)biphenyl-4-yloxy]ethyl} pyrrolidine-2-carboxylic acid (38) is a potent GlyT-1 inhibitor (IC50 = 59 nM). In vitro and in vivo assessment of CNS exposure indicates this compound is a likely substrate for active efflux transporters. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.017
• 作为产物：
  描述：

  4-bromo-2-(3-fluoro-phenylsulfanyl)-1-methoxybenzene 在 三溴化硼 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 2-[4-Bromo-2-(3-fluoro-phenylsulfanyl)-phenoxy]-ethanol
  参考文献：
  名称：

  The synthesis and SAR of 2-arylsulfanylphenyl-1-oxyalkylamino acids as GlyT-1 inhibitors

  摘要：

  Elevation of glycine levels by inhibition of the glycine transporter-1 (GlyT-1) and activation of the NMDA receptor is a potential strategy for the treatment of schizophrenia. A novel series of 2-arylsulfanylphenyl-1-oxyalkyl amino acids have been identified. The most prominent member of this series S-1-{2-[3-(3-fluoro-phenylsulfanyl)biphenyl-4-yloxy]ethyl} pyrrolidine-2-carboxylic acid (38) is a potent GlyT-1 inhibitor (IC50 = 59 nM). In vitro and in vivo assessment of CNS exposure indicates this compound is a likely substrate for active efflux transporters. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.017