6-dimethylamino-2-(4'-fluorophenyl)-1,3-benzothiazole | 1197943-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 6-dimethylamino-2-(4'-fluorophenyl)-1,3-benzothiazole
• 英文别名: 2-(4-fluorophenyl)-N,N-dimethyl-1,3-benzothiazol-6-amine
• CAS: 1197943-67-1
• 化学式: C₁₅H₁₃FN₂S
• 分子量: 272.346
• InChiKey: IEZDEOYLTJBRHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N,N-dimethyl-1,3-benzothiazol-6-amine 、 对溴氟苯 在 三叔丁基膦 、 palladium diacetate 、 caesium carbonate 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以6%的产率得到6-dimethylamino-2-(4'-fluorophenyl)-1,3-benzothiazole
  参考文献：
  名称：

  Synthesis and Evaluation of Three ¹⁸F-Labeled Aminophenylbenzothiazoles as Amyloid Imaging Agents

  摘要：

  We have developed three fluorine-18 labeled 6-(methyl)amino-2-(4'-fluorophenyl)-1,3-benzothiazoles, which display high in vitro binding affinity For human amyloid beta plaques (K-i <= 10 nM). The radiolabeled F, robes were synthesized by aromatic nucleophilic Substitution of the corresponding nitro precursor with F-18-fluoride, followed by deprotection of the BOC group if required. Determination of the octanol/water partition coefficient, biodistribution studies In mice, and in vivo mu PET studies in rats and a rhesus monkey showed that initial brain uptake was high and brain washout was fast in normal animals. Radiometabolites were quantified in plasma and brain of mice and in monkey plasma using HPLC. Of the tested compounds, [F-18]2 (6-amino-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole) shows the most favorable brain kinetics in mice, rats, and a monkey. Its polar plasma radiometabolites do not cross the blood-brain barrier. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as a PET brain amyloid imaging agent.

  DOI：

  10.1021/jm900871v

文献信息

• Synthesis and Evaluation of Three ¹⁸F-Labeled Aminophenylbenzothiazoles as Amyloid Imaging Agents
  作者：Kim Serdons、Koen Van Laere、Peter Janssen、Hank F. Kung、Guy Bormans、Alfons Verbruggen

  DOI：10.1021/jm900871v

  日期：2009.11.26

  We have developed three fluorine-18 labeled 6-(methyl)amino-2-(4'-fluorophenyl)-1,3-benzothiazoles, which display high in vitro binding affinity For human amyloid beta plaques (K-i <= 10 nM). The radiolabeled F, robes were synthesized by aromatic nucleophilic Substitution of the corresponding nitro precursor with F-18-fluoride, followed by deprotection of the BOC group if required. Determination of the octanol/water partition coefficient, biodistribution studies In mice, and in vivo mu PET studies in rats and a rhesus monkey showed that initial brain uptake was high and brain washout was fast in normal animals. Radiometabolites were quantified in plasma and brain of mice and in monkey plasma using HPLC. Of the tested compounds, [F-18]2 (6-amino-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole) shows the most favorable brain kinetics in mice, rats, and a monkey. Its polar plasma radiometabolites do not cross the blood-brain barrier. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as a PET brain amyloid imaging agent.