1-[5-Chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-3-methyl-piperazine | 745031-25-8

• 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: 1-[5-Chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-3-methyl-piperazine
• 英文别名: 1-[5-Chloro-2-(4-methoxyphenyl)sulfanylphenyl]-3-methylpiperazine
• CAS: 745031-25-8
• 化学式: C₁₈H₂₁ClN₂OS
• 分子量: 348.897
• InChiKey: JBSUWTAUXBQRAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[5-Chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-3-methyl-piperazine 在 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 32.0h， 生成 {4-[5-Chloro-2-(4-methoxy-phenylsulfanyl)-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
• 作为产物：
  描述：

  2-甲基哌嗪 在 palladium on activated charcoal 硫酸 、 氢气 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-[5-Chloro-2-(4-methoxy-phenylsulfanyl)-phenyl]-3-methyl-piperazine
  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

• ARYLOXYPHENYL AND ARYLSULFANYLPHENYL DERIVATIVES
  申请人：H. LUNDBECK A/S

  公开号：EP1458689B1

  公开（公告）日：2007-04-11