5-(4-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazole | 726196-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazole
• 英文别名: 1-(4-Methoxyphenyl)-5-(4-phenylmethoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1,2,4-triazole
• CAS: 726196-69-6
• 化学式: C₂₄H₂₀F₃N₃O₃
• 分子量: 455.436
• InChiKey: WFLMSLVNBFKDHC-UHFFFAOYSA-N

物化性质

• 沸点：
  573.0±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(4-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazole 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以64%的产率得到4-(1-(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazol-5-yl)phenol
  参考文献：
  名称：

  3-Substituted 1,5-Diaryl-1H-1,2,4-triazoles as Prospective PET Radioligands for Imaging Brain COX-1 in Monkey. Part 1: Synthesis and Pharmacology

  摘要：

  Cyclooxygenase-1 (COX-1) is a key enzyme in the biosynthesis of proinflammatory thromboxanes and prostaglandins and is found in glial and neuronal cells within brain. COX-1 expression is implicated in numerous neuroinflammatory states. We aim to find a direct-acting positron emission tomography (PET) radioligand for imaging COX-1 in human brain as a potential biomarker of neuroinflammation and for serving as a tool in drug development. Seventeen 3-substituted 1,5-diaryl-1H-1,2,4-triazoles were prepared as prospective COX-1 PET radioligands. From this set, three 1,5-(4-methoxypheny1)-1H-1,2,4-triazoles, carrying a 3-methoxy (5), 3-(1,1,1-trifluoroethoxy) (20), or 3-fluoromethoxy substituent (6), were selected for radioligand development, based mainly on their high affinities and selectivities for inhibiting human COX-1, absence of carboxyl group, moderate computed lipophilicities, and scope for radiolabeling with carbon-11 (t(1/2) = 20.4 min) or fluorine-18 (t(1/2) = 109.8 min). Methods were developed for producing [C-11]5, [C-11]20, and [d(2)-F-18]6 from hydroxy precursors in a form ready for intravenous injection for prospective evaluation in monkey with PET.

  DOI：

  10.1021/acschemneuro.8b00102
• 作为产物：
  描述：

  2-(4-(benzyloxy)benzoyl)-2-(4-methoxyphenyl)-hydrazinecarboxamide 在 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.6h， 生成 5-(4-(benzyloxy)phenyl)-1-(4-methoxyphenyl)-3-(2,2,2-trifluoroethoxy)-1H-1,2,4-triazole
  参考文献：
  名称：

  3-Substituted 1,5-Diaryl-1H-1,2,4-triazoles as Prospective PET Radioligands for Imaging Brain COX-1 in Monkey. Part 1: Synthesis and Pharmacology

  摘要：

  Cyclooxygenase-1 (COX-1) is a key enzyme in the biosynthesis of proinflammatory thromboxanes and prostaglandins and is found in glial and neuronal cells within brain. COX-1 expression is implicated in numerous neuroinflammatory states. We aim to find a direct-acting positron emission tomography (PET) radioligand for imaging COX-1 in human brain as a potential biomarker of neuroinflammation and for serving as a tool in drug development. Seventeen 3-substituted 1,5-diaryl-1H-1,2,4-triazoles were prepared as prospective COX-1 PET radioligands. From this set, three 1,5-(4-methoxypheny1)-1H-1,2,4-triazoles, carrying a 3-methoxy (5), 3-(1,1,1-trifluoroethoxy) (20), or 3-fluoromethoxy substituent (6), were selected for radioligand development, based mainly on their high affinities and selectivities for inhibiting human COX-1, absence of carboxyl group, moderate computed lipophilicities, and scope for radiolabeling with carbon-11 (t(1/2) = 20.4 min) or fluorine-18 (t(1/2) = 109.8 min). Methods were developed for producing [C-11]5, [C-11]20, and [d(2)-F-18]6 from hydroxy precursors in a form ready for intravenous injection for prospective evaluation in monkey with PET.

  DOI：

  10.1021/acschemneuro.8b00102