2-(p-methylaminophenyl)-7-(2-tosyloxyethoxy)imidazo[2,1-b]benzothiazole | 1240348-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(p-methylaminophenyl)-7-(2-tosyloxyethoxy)imidazo[2,1-b]benzothiazole
• CAS: 1240348-38-2
• 化学式: C₂₅H₂₃N₃O₄S₂
• 分子量: 493.607
• InChiKey: YCUUTYSKCUIXRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  81.93
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(p-methylaminophenyl)-7-(2-tosyloxyethoxy)imidazo[2,1-b]benzothiazole 在 Kryptofix222[18F]钾盐 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.33h， 生成 [18F]2-(p-methylaminophenyl)-7-(2-fluoroethoxy)imidazo[2,1-b]benzothiazole
  参考文献：
  名称：

  A Novel ¹⁸F-Labeled Imidazo[2,1-b]benzothiazole (IBT) for High-Contrast PET Imaging of β-Amyloid Plaques

  摘要：

  F-18-labeled imidazo[2,1-b]benzothiazole ([F-18]8) was synthesized and evaluated as a tracer for cerebral beta-amyloid deposits (A beta) by means of positron emission tomography (PET). [F-18]8 exhibits a high affinity to A beta and suitable brain uptake kinetics combined with a high metabolic stability in the brain. In a double transgenic APP/PS1 mouse model of Alzheimer's disease, we demonstrated a specific uptake of [F-18]8 in A beta-containing telencephalic brain regions. The specific binding of [F-18]8 to A beta was confirmed by regional brain biodistribution and autoradiography and correlated to immunohistochemistry staining. Analysis of brain sections of APP/PS1 mouse injected with a cocktail of [F-18]8 and reference compound [H-3]PiB revealed that the two tracers bind to A beta plaques in the brain of mouse in a comparable binding pattern. [F-18]8 represents the first high-contrast PET imaging agent for detection of A beta plaques in transgenic mouse model of Alzheimer's disease and holds promise for transfer to a clinical evaluation.

  DOI：

  10.1021/ml200123w
• 作为产物：
  描述：

  N-[4-(2-溴乙酰基)苯基)乙酰胺 在 三溴化硼 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-(p-methylaminophenyl)-7-(2-tosyloxyethoxy)imidazo[2,1-b]benzothiazole
  参考文献：
  名称：

  A Novel ¹⁸F-Labeled Imidazo[2,1-b]benzothiazole (IBT) for High-Contrast PET Imaging of β-Amyloid Plaques

  摘要：

  F-18-labeled imidazo[2,1-b]benzothiazole ([F-18]8) was synthesized and evaluated as a tracer for cerebral beta-amyloid deposits (A beta) by means of positron emission tomography (PET). [F-18]8 exhibits a high affinity to A beta and suitable brain uptake kinetics combined with a high metabolic stability in the brain. In a double transgenic APP/PS1 mouse model of Alzheimer's disease, we demonstrated a specific uptake of [F-18]8 in A beta-containing telencephalic brain regions. The specific binding of [F-18]8 to A beta was confirmed by regional brain biodistribution and autoradiography and correlated to immunohistochemistry staining. Analysis of brain sections of APP/PS1 mouse injected with a cocktail of [F-18]8 and reference compound [H-3]PiB revealed that the two tracers bind to A beta plaques in the brain of mouse in a comparable binding pattern. [F-18]8 represents the first high-contrast PET imaging agent for detection of A beta plaques in transgenic mouse model of Alzheimer's disease and holds promise for transfer to a clinical evaluation.

  DOI：

  10.1021/ml200123w