{4-[2-(4-Methoxy-phenylsulfanyl)-5-methyl-phenyl]-2-methyl-piperazin-1-yl}-acetic acid | 745031-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: {4-[2-(4-Methoxy-phenylsulfanyl)-5-methyl-phenyl]-2-methyl-piperazin-1-yl}-acetic acid
• 英文别名: 2-[4-[2-(4-methoxyphenyl)sulfanyl-5-methylphenyl]-2-methylpiperazin-1-yl]acetic acid
• CAS: 745031-36-1
• 化学式: C₂₁H₂₆N₂O₃S
• 分子量: 386.515
• InChiKey: UJZNDEGDKYJYIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲基哌嗪 在 palladium on activated charcoal sodium hydroxide 、 硫酸 、 氢气 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 52.0h， 生成 {4-[2-(4-Methoxy-phenylsulfanyl)-5-methyl-phenyl]-2-methyl-piperazin-1-yl}-acetic acid
  参考文献：
  名称：

  The synthesis and SAR of 2-arylsulfanyl-phenyl piperazinyl acetic acids as glyT-1 inhibitors

  摘要：

  Elevation of glycine levels and activation of the NMDA receptor by inhibition of the glycine transporter 1 (GlyT-1) is a potential strategy for the treatment of schizophrenia. A novel series of GlyT-1 inhibitors have been identified containing,the 2-arylsulfanyl-phenylpiperazine motif. The most prominent member of this series, (R)-4-[5-chloro-2-(4-methoxy-phenylsulfanyl)- phenyl]-2-methyl-piperazin-1-yl-acetic acid (31) is a potent glycine transporter-1 inhibitor (IC50 = 150 nM), which elevated glycine levels in rat ventral hippocampus as measured by microdialysis in vivo at doses of 1.2-4.6 mg/kg s.c. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.043

文献信息

• The synthesis and SAR of 2-arylsulfanyl-phenyl piperazinyl acetic acids as glyT-1 inhibitors
  作者：Garrick Smith、Thomas Ruhland、Gitte Mikkelsen、Kim Andersen、Claus Tornby Christoffersen、Lene Hjorth Alifrangis、Arne Mørk、Stephen P Wren、Neil Harris、Barry M Wyman、Guillaume Brandt

  DOI：10.1016/j.bmcl.2004.05.043

  日期：2004.8

  Elevation of glycine levels and activation of the NMDA receptor by inhibition of the glycine transporter 1 (GlyT-1) is a potential strategy for the treatment of schizophrenia. A novel series of GlyT-1 inhibitors have been identified containing,the 2-arylsulfanyl-phenylpiperazine motif. The most prominent member of this series, (R)-4-[5-chloro-2-(4-methoxy-phenylsulfanyl)- phenyl]-2-methyl-piperazin-1-yl-acetic acid (31) is a potent glycine transporter-1 inhibitor (IC50 = 150 nM), which elevated glycine levels in rat ventral hippocampus as measured by microdialysis in vivo at doses of 1.2-4.6 mg/kg s.c. (C) 2004 Elsevier Ltd. All rights reserved.