tert-butyl (1S,6R)-6-(3,4-dichlorophenyl)-1-(2-methoxy-2-oxoethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (1S,6R)-6-(3,4-dichlorophenyl)-1-(2-methoxy-2-oxoethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
• 化学式: C₂₀H₂₅Cl₂NO₄
• 分子量: 414.329
• InChiKey: ACNHRBGWRRQATG-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,6R)-6-(3,4-dichlorophenyl)-1-(2-methoxy-2-oxoethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1,1-dimethylethyl (1R,6S/1S,6R)-6-(3,4-dichlorophenyl)-1-(2-hydroxyethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
  参考文献：
  名称：

  6-(3,4-Dichlorophenyl)-1-[(Methyloxy)methyl]-3-azabicyclo[4.1.0]heptane: A New Potent and Selective Triple Reuptake Inhibitor

  摘要：

  A pharmacophore model for triple reuptake inhibitors and the new class of 1-(aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes were recently reported. Further investigation in this area led to the identification of a new series of potent and selective triple reuptake inhibitors endowed with good developability characteristics. Excellent bioavailability and brain penetration are associated with this series of 6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptanes together with high in vitro potency and selectivity at SERT, NET, and DAT. In vivo microdialysis experiments in different animal models and receptor occupancy studies in rat confirmed that derivative 17 showed an appropriate profile to further progression of the compound.

  DOI：

  10.1021/jm100481d
• 作为产物：
  描述：

  2-(3-(tert-butoxycarbonyl)-6-(3,4-dichlorophenyl)-3-azabicyclo[4.1.0]heptan-1-yl)acetic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 生成 tert-butyl (1S,6R)-6-(3,4-dichlorophenyl)-1-(2-methoxy-2-oxoethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
  参考文献：
  名称：

  6-(3,4-Dichlorophenyl)-1-[(Methyloxy)methyl]-3-azabicyclo[4.1.0]heptane: A New Potent and Selective Triple Reuptake Inhibitor

  摘要：

  A pharmacophore model for triple reuptake inhibitors and the new class of 1-(aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes were recently reported. Further investigation in this area led to the identification of a new series of potent and selective triple reuptake inhibitors endowed with good developability characteristics. Excellent bioavailability and brain penetration are associated with this series of 6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptanes together with high in vitro potency and selectivity at SERT, NET, and DAT. In vivo microdialysis experiments in different animal models and receptor occupancy studies in rat confirmed that derivative 17 showed an appropriate profile to further progression of the compound.

  DOI：

  10.1021/jm100481d

文献信息

• 6-(3,4-Dichlorophenyl)-1-[(Methyloxy)methyl]-3-azabicyclo[4.1.0]heptane: A New Potent and Selective Triple Reuptake Inhibitor
  作者：Fabrizio Micheli、Paolo Cavanni、Daniele Andreotti、Roberto Arban、Roberto Benedetti、Barbara Bertani、Michela Bettati、Letizia Bettelini、Giorgio Bonanomi、Simone Braggio、Renzo Carletti、Anna Checchia、Mauro Corsi、Elettra Fazzolari、Stefano Fontana、Carla Marchioro、Emilio Merlo-Pich、Michele Negri、Beatrice Oliosi、Emiliangelo Ratti、Kevin D. Read、Maja Roscic、Ilaria Sartori、Simone Spada、Giovanna Tedesco、Luca Tarsi、Silvia Terreni、Filippo Visentini、Alessandro Zocchi、Laura Zonzini、Romano Di Fabio

  DOI：10.1021/jm100481d

  日期：2010.7.8

  A pharmacophore model for triple reuptake inhibitors and the new class of 1-(aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes were recently reported. Further investigation in this area led to the identification of a new series of potent and selective triple reuptake inhibitors endowed with good developability characteristics. Excellent bioavailability and brain penetration are associated with this series of 6-(3,4-dichlorophenyl)-1-[(methyloxy)methyl]-3-azabicyclo[4.1.0]heptanes together with high in vitro potency and selectivity at SERT, NET, and DAT. In vivo microdialysis experiments in different animal models and receptor occupancy studies in rat confirmed that derivative 17 showed an appropriate profile to further progression of the compound.