spiperone tetraethyleneglycol tosylate | 1446685-12-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiperone tetraethyleneglycol tosylate
• 英文别名: 3-[2-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)ethyl]-8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
• CAS: 1446685-12-6
• 化学式: C₃₈H₄₈FN₃O₈S
• 分子量: 725.879
• InChiKey: ZYKKQKAUKNNEGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  51.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  114.92
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  spiperone tetraethyleneglycol tosylate 、 对甲苯磺酸 、 1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸三叔丁酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以73%的产率得到3-[2-(2-(2-(2-{4,7,10-tris(2-tert-butoxy-2-oxoethyl)-1,4,7,10-tetraazacyclodo-decan-1-yl}ethoxy)ethoxy)ethoxy)ethyl]-8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one tosylate
  参考文献：
  名称：

  Target-Specific Ligands and Gadolinium-Based Complexes for Imaging of Dopamine Receptors: Synthesis, Binding Affinity, and Relaxivity

  摘要：

  Magnetic resonance imaging (MRI) and positron emission tomography (PET) are two extremely important imaging modalities with unlimited tissue penetration. Molecular imaging is a field by which specific targets or biological processes are imaged. MRI, which is used for functional imaging and for the diagnosis of a broad range of pathologic conditions, suffers from limited specificity and intrinsically low sensitivity. One possibility to alleviate partially these limitations is to use contrast agents (CAs) and more importantly target-specific CAs. We have developed a modular synthesis of novel ligands and gadolinium(III)-based target-specific MRI CAs with high relaxivity and high binding affinity toward the dopamine receptors. The prepared ligands and MRI CAs are based on spiperone as targeting moiety. The prepared target-specific CAs can potentially be used for in vitro and possibly in vivo MR imaging of dopaminergic receptors. Importantly the ligands prepared using the modular approach presented in this paper may also be useful for other imaging modalities such as PET (or SPECT) by just replacing, at the last stage of the synthesis, the gadolinium cation by other metal cations having relatively long half-lives, such as Cu-64, Zr-89, In-11, and more.

  DOI：

  10.1021/jo400646k
• 作为产物：
  描述：

  三缩四乙二醇 在 4-二甲氨基吡啶 、 三乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 spiperone tetraethyleneglycol tosylate
  参考文献：
  名称：

  Target-Specific Ligands and Gadolinium-Based Complexes for Imaging of Dopamine Receptors: Synthesis, Binding Affinity, and Relaxivity

  摘要：

  Magnetic resonance imaging (MRI) and positron emission tomography (PET) are two extremely important imaging modalities with unlimited tissue penetration. Molecular imaging is a field by which specific targets or biological processes are imaged. MRI, which is used for functional imaging and for the diagnosis of a broad range of pathologic conditions, suffers from limited specificity and intrinsically low sensitivity. One possibility to alleviate partially these limitations is to use contrast agents (CAs) and more importantly target-specific CAs. We have developed a modular synthesis of novel ligands and gadolinium(III)-based target-specific MRI CAs with high relaxivity and high binding affinity toward the dopamine receptors. The prepared ligands and MRI CAs are based on spiperone as targeting moiety. The prepared target-specific CAs can potentially be used for in vitro and possibly in vivo MR imaging of dopaminergic receptors. Importantly the ligands prepared using the modular approach presented in this paper may also be useful for other imaging modalities such as PET (or SPECT) by just replacing, at the last stage of the synthesis, the gadolinium cation by other metal cations having relatively long half-lives, such as Cu-64, Zr-89, In-11, and more.

  DOI：

  10.1021/jo400646k