5,7-dihydroxy-2-(4'-fluorophenyl)-1,3-benzothiazole | 1126253-02-8

• 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: 5,7-dihydroxy-2-(4'-fluorophenyl)-1,3-benzothiazole
• 英文别名: 2-(4-Fluorophenyl)-1,3-benzothiazole-5,7-diol
• CAS: 1126253-02-8
• 化学式: C₁₃H₈FNO₂S
• 分子量: 261.276
• InChiKey: OTLZQFQXGJUPOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,7-dimethoxy-2-(4'-fluorophenyl)-1,3-benzothiazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到5,7-dihydroxy-2-(4'-fluorophenyl)-1,3-benzothiazole
  参考文献：
  名称：

  Synthesis and Evaluation of ¹⁸F-Labeled 2-Phenylbenzothiazoles as Positron Emission Tomography Imaging Agents for Amyloid Plaques in Alzheimer’s Disease

  摘要：

  Imaging agents targeting amyloid beta(A beta) may be useful for early diagnosis and follow-up of treatment of patients with Alzheimer's disease (AD). Three of five tested 2-(4'-fluorophenyl)-1,3-benzothiazoles displayed high binding affinities for A beta plaques in AD human brain homogenates (K-i between 2.2 and 22.5 nM). They all contained the F-18-label directly attached to the aromatic ring and were synthesized starting from the nitro precursor. Determination of the partition coefficient, biodistribution studies in normal mice, and in vivo mu PET studies in normal rats showed that their initial brain uptake was high and brain washout was fast. The most promising compound [F-18]5, or 6- methyl-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole, seemed to be metabolically stable in the brain, and its plasma radiometabolites, which do not cross the blood-brain barrier, were determined. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as an A beta plaque imaging agent for the study of patients with AD.

  DOI：

  10.1021/jm8013376

文献信息

• Synthesis and Evaluation of ¹⁸F-Labeled 2-Phenylbenzothiazoles as Positron Emission Tomography Imaging Agents for Amyloid Plaques in Alzheimer’s Disease
  作者：Kim Serdons、Christelle Terwinghe、Peter Vermaelen、Koen Van Laere、Hank Kung、Luc Mortelmans、Guy Bormans、Alfons Verbruggen

  DOI：10.1021/jm8013376

  日期：2009.3.12

  Imaging agents targeting amyloid beta(A beta) may be useful for early diagnosis and follow-up of treatment of patients with Alzheimer's disease (AD). Three of five tested 2-(4'-fluorophenyl)-1,3-benzothiazoles displayed high binding affinities for A beta plaques in AD human brain homogenates (K-i between 2.2 and 22.5 nM). They all contained the F-18-label directly attached to the aromatic ring and were synthesized starting from the nitro precursor. Determination of the partition coefficient, biodistribution studies in normal mice, and in vivo mu PET studies in normal rats showed that their initial brain uptake was high and brain washout was fast. The most promising compound [F-18]5, or 6- methyl-2-(4'-[F-18]fluorophenyl)-1,3-benzothiazole, seemed to be metabolically stable in the brain, and its plasma radiometabolites, which do not cross the blood-brain barrier, were determined. The preliminary results strongly suggest that this new fluorinated compound is a promising candidate as an A beta plaque imaging agent for the study of patients with AD.