2-[(2,4-dinitrophenyl)thio]-N,N-dimethylbenzamide | 606937-71-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(2,4-dinitrophenyl)thio]-N,N-dimethylbenzamide
• 英文别名: N,N-dimethyl-2-(2,4-dinitrophenylthio)benzamide；2-(2,4-dinitrophenyl)sulfanyl-N,N-dimethylbenzamide
• CAS: 606937-71-7
• 化学式: C₁₅H₁₃N₃O₅S
• 分子量: 347.351
• InChiKey: PIYAJWPBYNIBAC-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• 沸点：
  505.0±50.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(2,4-dinitrophenyl)thio]-N,N-dimethylbenzamide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到2-[(2,4-dinitrophenyl)thio]-N,N-dimethylbenzenemethaneamine
  参考文献：
  名称：

  Fluorinated Diaryl Sulfides as Serotonin Transporter Ligands:  Synthesis, Structure−Activity Relationship Study, and in Vivo Evaluation of Fluorine-18-Labeled Compounds as PET Imaging Agents

  摘要：

  A series of new, fluorine-containing substituted diphenyl sulfides was synthesized to serve as candidate ligands for positron emission tomography (PET) imaging of the serotonin transporter (SERT) and to further probe the structure-activity relationship (SAR) of this class of compounds. Candidate compounds were assayed for their affinities to the monoamine transporters (SERT, norepinephrine transporter (NET), and dopamine transporter (DAT)) in competitive binding experiments in vitro using cloned human transporters. From these in vitro assays, four compounds (7c-f) were chosen for further evaluation. All four compounds have nanomolar affinity for SERT (K-i 1.46 nM, 1.04 nM,1.83 nM, and 3.58 nM for 7c, 7d, 7e, and 7f, respectively). The F-18-labeled compounds, 16 and 18a-c, were prepared via a two-step radiosynthesis. Biodistribution studies in rats indicated that the F-18-labeled compounds localized in brain regions with high concentrations of SERT. Furthermore, competition experiments demonstrated that the binding of these radioligands in the rat brain was saturable, specific, and selective to SERT. Specific binding in the rat hypothalamus peaked at 5.6 for ligand 16 and 4.4 for 18b at 90 min after radioactivity administration. For ligand 18a, this same ratio was 8.4 at 120 min postinjection, while compound 18c displayed a lower-specific binding ratio of 2.4. In summary, four F-18-labeled ligands were prepared and evaluated as candidate PET imaging agents for SERT. Among these four ligands, three appear to be promising radioligands suitable for the labeling of SERT in vivo, with 18a providing a higher specific binding in vivo than 16 or 18b.

  DOI：

  10.1021/jm0400808
• 作为产物：
  描述：

  1-溴-2,4-二硝基苯 在 氯化亚砜 、 铜 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(2,4-dinitrophenyl)thio]-N,N-dimethylbenzamide
  参考文献：
  名称：

  Fluorinated Diaryl Sulfides as Serotonin Transporter Ligands:  Synthesis, Structure−Activity Relationship Study, and in Vivo Evaluation of Fluorine-18-Labeled Compounds as PET Imaging Agents

  摘要：

  A series of new, fluorine-containing substituted diphenyl sulfides was synthesized to serve as candidate ligands for positron emission tomography (PET) imaging of the serotonin transporter (SERT) and to further probe the structure-activity relationship (SAR) of this class of compounds. Candidate compounds were assayed for their affinities to the monoamine transporters (SERT, norepinephrine transporter (NET), and dopamine transporter (DAT)) in competitive binding experiments in vitro using cloned human transporters. From these in vitro assays, four compounds (7c-f) were chosen for further evaluation. All four compounds have nanomolar affinity for SERT (K-i 1.46 nM, 1.04 nM,1.83 nM, and 3.58 nM for 7c, 7d, 7e, and 7f, respectively). The F-18-labeled compounds, 16 and 18a-c, were prepared via a two-step radiosynthesis. Biodistribution studies in rats indicated that the F-18-labeled compounds localized in brain regions with high concentrations of SERT. Furthermore, competition experiments demonstrated that the binding of these radioligands in the rat brain was saturable, specific, and selective to SERT. Specific binding in the rat hypothalamus peaked at 5.6 for ligand 16 and 4.4 for 18b at 90 min after radioactivity administration. For ligand 18a, this same ratio was 8.4 at 120 min postinjection, while compound 18c displayed a lower-specific binding ratio of 2.4. In summary, four F-18-labeled ligands were prepared and evaluated as candidate PET imaging agents for SERT. Among these four ligands, three appear to be promising radioligands suitable for the labeling of SERT in vivo, with 18a providing a higher specific binding in vivo than 16 or 18b.

  DOI：

  10.1021/jm0400808

文献信息

• Fluorinated phenyl thiophenyl derivatives and their use for imaging serotonin transporters
  申请人：——

  公开号：US20030236234A1

  公开（公告）日：2003-12-25

  This invention relates to novel fluorinated phenyl thiphenyl (also named diarylsulfide) derivatives and their use in Positron Emission Tomagraphy (PET) imaging of Serotonin Transporters (SERTS). The present invention also provides diagnostic compositions comprising the novel compounds of the present invention, and a pharmaceutically acceptable carrier or diluent. The invention further provides a method of imaging SERTS, comprising introducing into a patient a detectable quantity of a labeled compound of the present invetion, or a pharmaceutically acceptable salt, ester, amide or prodrug thereof.

  本发明涉及一种新型的氟化苯基噻吩（也称二芳基硫醚）衍生物及其在正电子发射断层扫描（PET）成像中用于血清素转运体（SERTS）的应用。本发明还提供了包含本发明新化合物的诊断组合物，并且还包括药学上可接受的载体或稀释剂。本发明还提供了一种成像SERTS的方法，包括向患者引入本发明标记化合物的可检测量，或其药学上可接受的盐、酯、酰胺或前药。
• Carbon-11 and fluorine-18 labeled radioligands for positron emission tomography (PET) imaging for the brain serotonin transporters
  申请人：Huang Yiyun

  公开号：US20110097274A1

  公开（公告）日：2011-04-28

  This invention provides a compound having the structure: This invention also provides for related compounds and pharmaceutical compositions. This invention further provides for a compound that can be used for non-invasive method for positron emission tomography (PET) imaging of serotonin transporter sites in mammals comprising labeling serotonin transporter sites (SERT) with an image-generating amount of the radiolabeled compound disclosed herein and measuring spatial distribution of the compound in the mammal by PET so as to thereby image the serotonin transporter sites.

  这项发明提供了一种具有以下结构的化合物：此外，本发明还提供了相关的化合物和制药组合物。此外，本发明还提供了一种化合物，可用于非侵入性的正电子发射断层扫描（PET）成像方法，用于哺乳动物中的血清素转运体位点成像，包括使用本文所述的放射性标记化合物标记血清素转运体位点（SERT），并通过PET测量哺乳动物中化合物的空间分布，从而成像血清素转运体位点。
• US7041851B2
  申请人：——

  公开号：US7041851B2

  公开（公告）日：2006-05-09
• [EN] FLUORINATED PHENYL THIOPHENYL DERIVATIVES AND THEIR USE FOR IMAGING SEROTONIN TRANSPORTERS<br/>[FR] DERIVES FLUORES DE PHENYL THIOPHENYL ET LEUR UTILISATION DANS L'IMAGERIE DE TRANSPORTEURS DE LA SEROTONINE
  申请人：KUNG HANK F

  公开号：WO2003078393A2

  公开（公告）日：2003-09-25

  This invention relates to novel fluorinated phenyl thiphenyl (also named diarylsulfide) derivatives and their use in Positron Emission Tomagraphy (PET) imaging of Serotonin Transporters (SERTS). The present invention also provides diagnostic compositions comprising the novel compounds of the present invention, and a pharmaceutically acceptable carrier or diluent. The invention further provides a method of imaging SERTS, comprising introducing into a patient a detectable quantity of a labeled compound of the present invention, or a pharmaceutically acceptable salt, ester, amide or prodrug thereof.
• Fluorinated Diaryl Sulfides as Serotonin Transporter Ligands:  Synthesis, Structure−Activity Relationship Study, and in Vivo Evaluation of Fluorine-18-Labeled Compounds as PET Imaging Agents
  作者：Yiyun Huang、Sung-A Bae、Zhihong Zhu、Ningning Guo、Bryan L. Roth、Marc Laruelle

  DOI：10.1021/jm0400808

  日期：2005.4.1

  A series of new, fluorine-containing substituted diphenyl sulfides was synthesized to serve as candidate ligands for positron emission tomography (PET) imaging of the serotonin transporter (SERT) and to further probe the structure-activity relationship (SAR) of this class of compounds. Candidate compounds were assayed for their affinities to the monoamine transporters (SERT, norepinephrine transporter (NET), and dopamine transporter (DAT)) in competitive binding experiments in vitro using cloned human transporters. From these in vitro assays, four compounds (7c-f) were chosen for further evaluation. All four compounds have nanomolar affinity for SERT (K-i 1.46 nM, 1.04 nM,1.83 nM, and 3.58 nM for 7c, 7d, 7e, and 7f, respectively). The F-18-labeled compounds, 16 and 18a-c, were prepared via a two-step radiosynthesis. Biodistribution studies in rats indicated that the F-18-labeled compounds localized in brain regions with high concentrations of SERT. Furthermore, competition experiments demonstrated that the binding of these radioligands in the rat brain was saturable, specific, and selective to SERT. Specific binding in the rat hypothalamus peaked at 5.6 for ligand 16 and 4.4 for 18b at 90 min after radioactivity administration. For ligand 18a, this same ratio was 8.4 at 120 min postinjection, while compound 18c displayed a lower-specific binding ratio of 2.4. In summary, four F-18-labeled ligands were prepared and evaluated as candidate PET imaging agents for SERT. Among these four ligands, three appear to be promising radioligands suitable for the labeling of SERT in vivo, with 18a providing a higher specific binding in vivo than 16 or 18b.