(S)-1-{2-[4-bromo-2-(3-fluoro-phenylsulfanyl)-phenoxy]-ethyl}-pyrrolidine-2-carboxylic acid tert-butyl ester | 791642-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-{2-[4-bromo-2-(3-fluoro-phenylsulfanyl)-phenoxy]-ethyl}-pyrrolidine-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-1-[2-[4-bromo-2-(3-fluorophenyl)sulfanylphenoxy]ethyl]pyrrolidine-2-carboxylate
• CAS: 791642-79-0
• 化学式: C₂₃H₂₇BrFNO₃S
• 分子量: 496.441
• InChiKey: SWNWDGDPUMZRLD-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

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

文献信息

• [EN] AROMATIC OXYPHENYL AND AROMATIC SULFANYLPHENYL DERIVATIVES<br/>[FR] DERIVES D'OXYPHENYL AROMATIQUE ET DE SYLFANYLPHENYL AROMATIQUE
  申请人：LUNDBECK & CO AS H

  公开号：WO2004096761A1

  公开（公告）日：2004-11-11

  The present invention relates to compounds of formula I wherein the substituents are as defined below. The compounds of formula I are useful for the treatment of diseases such as schizophrenia, including both the positive and the negative symptoms of schizophrenia and other psychoses.

  本发明涉及公式I的化合物，其中取代基如下所定义。公式I的化合物对于治疗精神分裂症等疾病是有用的，包括精神分裂症和其他精神病的阳性和阴性症状。
• Aromatic oxyphenyl and aromatic sulfanylphenyl derivatives
  申请人：Smith P. Garrick

  公开号：US20060235003A1

  公开（公告）日：2006-10-19

  The present invention relates to compounds of formula I wherein the substituents are as defined below. The compounds of formula are useful for the treatment of diseases such as schizophrenia, including both the positive and the negative symptoms of schizophrenia and other psychoses.

  本发明涉及式I的化合物，其中取代基如下所定义。式I的化合物可用于治疗疾病，如精神分裂症，包括精神分裂症的阳性症状和阴性症状以及其他精神病。
• EP1622868A1
  申请人：——

  公开号：EP1622868A1

  公开（公告）日：2006-02-08
• 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.