3-[2-(2-(2-hydroxyethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one | 1446685-09-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-[2-(2-(2-hydroxyethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
• CAS: 1446685-09-1
• 化学式: C₂₈H₃₈FN₃O₅
• 分子量: 515.625
• InChiKey: VIRNGHCOULVWGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  37.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  74.71
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-[2-(2-(2-hydroxyethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到3-[2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
  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：

  1-苯基-1,3,8-三唑螺环(4,5)十烷-4-酮 在 二异丙胺 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 3-[2-(2-(2-hydroxyethoxy)ethoxy)ethyl]-8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
  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