Toluene-4-sulfonic acid 2-[4-(2-dimethylaminomethyl-phenylsulfanyl)-3-nitro-phenyl]-ethyl ester | 627488-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid 2-[4-(2-dimethylaminomethyl-phenylsulfanyl)-3-nitro-phenyl]-ethyl ester
• 英文别名: 2-[4-[2-[(Dimethylamino)methyl]phenyl]sulfanyl-3-nitrophenyl]ethyl 4-methylbenzenesulfonate
• CAS: 627488-97-5
• 化学式: C₂₄H₂₆N₂O₅S₂
• 分子量: 486.613
• InChiKey: XPKKVKQAOYFLIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 2-[4-(2-dimethylaminomethyl-phenylsulfanyl)-3-nitro-phenyl]-ethyl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 生成 1-[2-[4-(2-(18F)fluoranylethyl)-2-nitrophenyl]sulfanylphenyl]-N,N-dimethylmethanamine
  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：

  methyl 4-bromo-3-nitrophenylacetate 在 吡啶 、 氯化亚砜 、 硼烷四氢呋喃络合物 、 铜 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Toluene-4-sulfonic acid 2-[4-(2-dimethylaminomethyl-phenylsulfanyl)-3-nitro-phenyl]-ethyl ester
  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

• Huang, Y.; Zhu, Z.; Bae, S. A., Journal of Labelled Compounds and Radiopharmaceuticals, 2003, vol. 46, p. S57 - S57
  作者：Huang, Y.、Zhu, Z.、Bae, S. A.、Hwang, D. R.、Narendran, R.、Phan, V.、Erritzoe, D.、Talbot, P. S.、Laruelle, M.

  DOI：——

  日期：——
• 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.