3-Chlor-5,6-dihydroxy-pyridazin | 17276-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-Chlor-5,6-dihydroxy-pyridazin
• 英文别名: 6-Chlor-pyridazin-3,4-diol；6-chloro-1,2-dihydro-pyridazine-3,4-dione；6-chloro-1,2-dihydropyridazine-3,4-dione
• CAS: 17276-75-4
• 化学式: C₄H₃ClN₂O₂
• 分子量: 146.533
• InChiKey: GEBURLIKOPEEQE-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲基甲基醚 、 3-Chlor-5,6-dihydroxy-pyridazin 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以40%的产率得到6-chloro-3,4-bis(methoxymethoxy)pyridazine
  参考文献：
  名称：

  Synthesis and preliminary evaluation of 4-hydroxy-6-(3-[11C]methoxyphenethyl)pyridazin-3(2H)-one, a 11C-labeled -amino acid oxidase (DAAO) inhibitor for PET imaging

  摘要：

  Selective DAAO inhibitors have demonstrated promising therapeutic effects in clinical studies, including clinically alleviating symptoms of schizophrenic patients and ameliorating cognitive function in Alzheimer's patients with early phase. Herein we report the synthesis and preliminary evaluation of a C-11-labeled positron emission tomography ligand based on a DAAO inhibitor, DAO-1903 (8). C-11-Isotopologue of 8 was prepared in high radiochemical yield with high radiochemical purity (> 99%) and high molar activity (> 37 GBq/umol). In vitro autoradiography studies indicated that the ligand possessed high in vitro specific binding to DAAO, while in vivo dynamic PET studies demonstrated that [C-11]8 failed to cross the blood-brain barrier possibly due to moderate brain efflux mechanism. Further chemical scaffold optimization is necessary to overcome limited brain permeability and improve specific binding.

  DOI：

  10.1016/j.bmcl.2020.127326
• 作为产物：
  描述：

  3,4-bis(benzyloxy)-6-chloropyridazine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以84%的产率得到3-Chlor-5,6-dihydroxy-pyridazin
  参考文献：
  名称：

  Synthesis and preliminary evaluation of 4-hydroxy-6-(3-[11C]methoxyphenethyl)pyridazin-3(2H)-one, a 11C-labeled -amino acid oxidase (DAAO) inhibitor for PET imaging

  摘要：

  Selective DAAO inhibitors have demonstrated promising therapeutic effects in clinical studies, including clinically alleviating symptoms of schizophrenic patients and ameliorating cognitive function in Alzheimer's patients with early phase. Herein we report the synthesis and preliminary evaluation of a C-11-labeled positron emission tomography ligand based on a DAAO inhibitor, DAO-1903 (8). C-11-Isotopologue of 8 was prepared in high radiochemical yield with high radiochemical purity (> 99%) and high molar activity (> 37 GBq/umol). In vitro autoradiography studies indicated that the ligand possessed high in vitro specific binding to DAAO, while in vivo dynamic PET studies demonstrated that [C-11]8 failed to cross the blood-brain barrier possibly due to moderate brain efflux mechanism. Further chemical scaffold optimization is necessary to overcome limited brain permeability and improve specific binding.

  DOI：

  10.1016/j.bmcl.2020.127326