5-bromo-2-(3-fluoro-phenylsulfanyl)-phenol | 905815-92-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-bromo-2-(3-fluoro-phenylsulfanyl)-phenol
• 英文别名: 5-Bromo-2-(3-fluorophenyl)sulfanylphenol
• CAS: 905815-92-1
• 化学式: C₁₂H₈BrFOS
• 分子量: 299.163
• InChiKey: RAEBEIJAIQNCPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(3-fluoro-phenylsulfanyl)-phenol 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 三氟甲磺酸酐 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (S)-1-{2-[4-(3-fluoro-phenylsulfanyl)-biphenyl-3-yloxy]-ethyl}-pyrrolidine-2-carboxylic acid
  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-溴-1-碘-2-甲氧基苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium tert-butylate 、 三溴化硼 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 5-bromo-2-(3-fluoro-phenylsulfanyl)-phenol
  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

文献信息

• US7612068B2
  申请人：——

  公开号：US7612068B2

  公开（公告）日：2009-11-03
• The synthesis and SAR of 2-arylsulfanylphenyl-1-oxyalkylamino acids as GlyT-1 inhibitors
  作者：Garrick Smith、Gitte Mikkelsen、Jørgen Eskildsen、Christoffer Bundgaard

  DOI：10.1016/j.bmcl.2006.05.017

  日期：2006.8

  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.