3-chloro-8-fluoroisoquinoline | 1394003-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-chloro-8-fluoroisoquinoline
• CAS: 1394003-78-1
• 化学式: C₉H₅ClFN
• 分子量: 181.597
• InChiKey: KPWUPANJZPWPEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-氮杂吲哚 、 3-chloro-8-fluoroisoquinoline 在 [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以37%的产率得到8-fluoro-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinoline
  参考文献：
  名称：

  Discovery of 6-(Fluoro-¹⁸F)-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinolin-5-amine ([¹⁸F]-MK-6240): A Positron Emission Tomography (PET) Imaging Agent for Quantification of Neurofibrillary Tangles (NFTs)

  摘要：

  Neurofibrillary tangles (NFTs) made up of aggregated tau protein have been identified as the pathologic hallmark of several neurodegenerative diseases including Alzheimer's disease. In vivo detection of NFTs using PET imaging represents a unique opportunity to develop a pharmacodynamic tool to accelerate the discovery of new disease modifying therapeutics targeting tau pathology. Herein, we present the discovery of 6-(fluoro-F-18)-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinolin-5-amine, 6 ([F-18]-MK-6240), as a novel PET tracer for detecting NFTs. 6 exhibits high specificity and selectivity for binding to NFTs, with suitable physicochemical properties and in vivo pharmacokinetics.

  DOI：

  10.1021/acs.jmedchem.6b00166
• 作为产物：
  描述：

  1,3-dichloro-8-fluoroisoquinoline 在 磷化氢 、 氢碘酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 以79%的产率得到3-chloro-8-fluoroisoquinoline
  参考文献：
  名称：

  Discovery of 6-(Fluoro-¹⁸F)-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinolin-5-amine ([¹⁸F]-MK-6240): A Positron Emission Tomography (PET) Imaging Agent for Quantification of Neurofibrillary Tangles (NFTs)

  摘要：

  Neurofibrillary tangles (NFTs) made up of aggregated tau protein have been identified as the pathologic hallmark of several neurodegenerative diseases including Alzheimer's disease. In vivo detection of NFTs using PET imaging represents a unique opportunity to develop a pharmacodynamic tool to accelerate the discovery of new disease modifying therapeutics targeting tau pathology. Herein, we present the discovery of 6-(fluoro-F-18)-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinolin-5-amine, 6 ([F-18]-MK-6240), as a novel PET tracer for detecting NFTs. 6 exhibits high specificity and selectivity for binding to NFTs, with suitable physicochemical properties and in vivo pharmacokinetics.

  DOI：

  10.1021/acs.jmedchem.6b00166