| 1350900-72-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1350900-72-9
• 化学式: C₇H₅FO₂
• 分子量: 139.115
• InChiKey: DOULGHINSFURSM-COJKEBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  、 1-(1,4-benzodioxine-6-yl)piperazine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 6-(4-[4-[¹⁸F]fluoro-3-hydroxybenzyl]piperazine-1-yl)benzodioxin
  参考文献：
  名称：

  Evaluation of ¹⁸F-Labeled Benzodioxine Piperazine-Based Dopamine D₄ Receptor Ligands: Lipophilicity as a Determinate of Nonspecific Binding

  摘要：

  Derivatization of the putative neuroleptic 1-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-4-(4-fluorobenzyl)-piperazine (3a) led to a series of new dopamine receptor D-4 ligands displaying high affinity (K-i = 1.1-15 nM) and D-2/D-4 subtype selectivities of about 800-6700. These ligands were labeled with the short-lived positron emitter fluorine-18 and analyzed for their potential application for imaging studies by positron emission tomography (PET). In vitro autoradiography was used to determine their nonspecific binding behavior as a result of their structural and thus physicochemical properties. The biodistribution, in vivo stability, and brain uptake of the most promising D-4 radioligand candidate were determined. This proved to be 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-((6-fluoropyridin-3-yl)methyl)piperazine ([F-18]3d), which revealed an excellent binding pattern with a high selectivity and limited nonspecific binding in vitro. This analogue also exhibited a high stability and an extremely high brain uptake in vivo with specific binding in hippocampus, cortex, colliculus, and cerebellum as determined by ex vivo autoradiography. Thus, [F-18]3d appears as a suitable D-4 radioligand for in vivo imaging, encouraging continued evaluation by PET studies.

  DOI：

  10.1021/jm200762g
• 作为产物：
  描述：

  [18F]-3-benzyloxy-4-fluorobenzaldehyde 在 ammonium formate 、 钯 作用下， 生成
  参考文献：
  名称：

  Evaluation of ¹⁸F-Labeled Benzodioxine Piperazine-Based Dopamine D₄ Receptor Ligands: Lipophilicity as a Determinate of Nonspecific Binding

  摘要：

  Derivatization of the putative neuroleptic 1-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-4-(4-fluorobenzyl)-piperazine (3a) led to a series of new dopamine receptor D-4 ligands displaying high affinity (K-i = 1.1-15 nM) and D-2/D-4 subtype selectivities of about 800-6700. These ligands were labeled with the short-lived positron emitter fluorine-18 and analyzed for their potential application for imaging studies by positron emission tomography (PET). In vitro autoradiography was used to determine their nonspecific binding behavior as a result of their structural and thus physicochemical properties. The biodistribution, in vivo stability, and brain uptake of the most promising D-4 radioligand candidate were determined. This proved to be 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-4-((6-fluoropyridin-3-yl)methyl)piperazine ([F-18]3d), which revealed an excellent binding pattern with a high selectivity and limited nonspecific binding in vitro. This analogue also exhibited a high stability and an extremely high brain uptake in vivo with specific binding in hippocampus, cortex, colliculus, and cerebellum as determined by ex vivo autoradiography. Thus, [F-18]3d appears as a suitable D-4 radioligand for in vivo imaging, encouraging continued evaluation by PET studies.

  DOI：

  10.1021/jm200762g