3-Naphthalen-2-ylpyrrole-2,5-dione | 1210476-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Naphthalen-2-ylpyrrole-2,5-dione
• CAS: 1210476-44-0
• 化学式: C₁₄H₉NO₂
• 分子量: 223.231
• InChiKey: ZAQYRMHPEPVNNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Naphthalen-2-ylpyrrole-2,5-dione 、 (乙氧基羰基甲基)二甲基溴化硫鎓 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 1.5h， 生成 ethyl 1-naphthalen-2-yl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate
  参考文献：
  名称：

  1-(Aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes and 6-(Aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes: A New Series of Potent and Selective Triple Reuptake Inhibitors

  摘要：

  The discovery of new highly potent and selective triple reuptake inhibitors is reported. The new classes of 1-(ary1)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes and 6-(aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes are described together with detailed SA R. Appropriate decoration of the scaffolds was achieved with the help of a triple reuptake inhibitor pharmacophore model detailed here. Selected derivatives showed good oral bioavailability ( > 30%) and brain penetration (B/B > 4) in rats associated with high in vitro potency and selectivity at SERT, NET, and DAT. Among these compounds, microdialysis and in vivo experiments confirm that derivative 15 has an appropriate developability profile to be considered for further progression.

  DOI：

  10.1021/jm901818u
• 作为产物：
  描述：

  马来酰亚胺 、 2-萘胺 在 亚硝酸特丁酯 、 copper dichloride 、 2,6-二甲基吡啶 作用下， 以 乙腈 、 异丙醇 为溶剂， 反应 0.5h， 生成 3-Naphthalen-2-ylpyrrole-2,5-dione
  参考文献：
  名称：

  1-(Aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes and 6-(Aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes: A New Series of Potent and Selective Triple Reuptake Inhibitors

  摘要：

  The discovery of new highly potent and selective triple reuptake inhibitors is reported. The new classes of 1-(ary1)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes and 6-(aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes are described together with detailed SA R. Appropriate decoration of the scaffolds was achieved with the help of a triple reuptake inhibitor pharmacophore model detailed here. Selected derivatives showed good oral bioavailability ( > 30%) and brain penetration (B/B > 4) in rats associated with high in vitro potency and selectivity at SERT, NET, and DAT. Among these compounds, microdialysis and in vivo experiments confirm that derivative 15 has an appropriate developability profile to be considered for further progression.

  DOI：

  10.1021/jm901818u

文献信息

• MALEIIMIDE ANTI-TUMOR PHOSPHATASE INHIBITORS
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1722781A2

  公开（公告）日：2006-11-22
• [EN] MALEIIMIDE ANTI-TUMOR PHOSPHATASE INHIBITORS<br/>[FR] INHIBITEURS DE PHOSPHATASE ANTITUMORAUX A BASE DE MALEIIMIDE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2005081972A2

  公开（公告）日：2005-09-09

  The present invention features maleiimide compounds, pharmaceutical compositions of maleiimide compounds and methods of treating a patient suffering from cancer, the method comprising administering to a patient one or more maleiimide compounds of the invention.
• 1-(Aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes and 6-(Aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes: A New Series of Potent and Selective Triple Reuptake Inhibitors
  作者：Fabrizio Micheli、Paolo Cavanni、Roberto Arban、Roberto Benedetti、Barbara Bertani、Michela Bettati、Letizia Bettelini、Giorgio Bonanomi、Simone Braggio、Anna Checchia、Silvia Davalli、Romano Di Fabio、Elettra Fazzolari、Stefano Fontana、Carla Marchioro、Doug Minick、Michele Negri、Beatrice Oliosi、Kevin D. Read、Ilaria Sartori、Giovanna Tedesco、Luca Tarsi、Silvia Terreni、Filippo Visentini、Alessandro Zocchi、Laura Zonzini

  DOI：10.1021/jm901818u

  日期：2010.3.25

  The discovery of new highly potent and selective triple reuptake inhibitors is reported. The new classes of 1-(ary1)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes and 6-(aryl)-6-[alkoxyalkyl]-3-azabicyclo[3.1.0]hexanes are described together with detailed SA R. Appropriate decoration of the scaffolds was achieved with the help of a triple reuptake inhibitor pharmacophore model detailed here. Selected derivatives showed good oral bioavailability ( > 30%) and brain penetration (B/B > 4) in rats associated with high in vitro potency and selectivity at SERT, NET, and DAT. Among these compounds, microdialysis and in vivo experiments confirm that derivative 15 has an appropriate developability profile to be considered for further progression.