6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline | 1268963-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline
• 英文别名: 6-[1-(2-Bromopyridin-3-yl)-5-methyltriazol-4-yl]quinoline
• CAS: 1268963-76-3
• 化学式: C₁₇H₁₂BrN₅
• 分子量: 366.22
• InChiKey: XRIFGSSUSOUQJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline 在 potassium [¹⁸F]fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成 6-[1-(2-(18)F-fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline
  参考文献：
  名称：

  Synthesis and evaluation of 6-[1-(2-[18F]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline for positron emission tomography imaging of the metabotropic glutamate receptor type 1 in brain

  摘要：

  The purpose of this study was to synthesize 6-[1-(2-[F-18]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline ([F-18]FPTQ, [F-18]7a) and to evaluate its potential as a positron emission tomography ligand for imaging metabotropic glutamate receptor type 1 (mGluR1) in the rat brain. Compound [F-18]7a was synthesized by [F-18] fluorination of 6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl] quinoline (7b) with potassium [F-18] fluoride. At the end of synthesis, 1280-1830 MBq (n = 8) of [F-18]7a was obtained with >98% radiochemical purity and 118-237 GBq/mu mol specific activity using 3300-4000 MBq of [F-18]F . In vitro autoradiography showed that [F-18]7a had high specific binding with mGluR1 in the rat brain. Biodistribution study using a dissection method and small-animal PET showed that [F-18]7a had high uptake in the rat brain. The uptake of radioactivity in the cerebellum was reduced by unlabeled 7a and mGluR1-selective ligand JNJ-16259685 (2), indicating that [F-18]7a had in vivo specific binding with mGluR1. Because of a low amount of radiolabeled metabolite present in the brain, [F-18]7a may have a limiting potential for the in vivo imaging of mGluR1 by PET. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.048
• 作为产物：
  描述：

  1-(2-bromo-3-pyridyl)-5-methyl-4-(tri-n-butylstannyl)-1H-1,2,3-triazole 、 6-喹啉基三氟甲烷磺酸酯 在 copper(l) iodide 、 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以52%的产率得到6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline
  参考文献：
  名称：

  Synthesis and evaluation of 6-[1-(2-[18F]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline for positron emission tomography imaging of the metabotropic glutamate receptor type 1 in brain

  摘要：

  The purpose of this study was to synthesize 6-[1-(2-[F-18]fluoro-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl]quinoline ([F-18]FPTQ, [F-18]7a) and to evaluate its potential as a positron emission tomography ligand for imaging metabotropic glutamate receptor type 1 (mGluR1) in the rat brain. Compound [F-18]7a was synthesized by [F-18] fluorination of 6-[1-(2-bromo-3-pyridyl)-5-methyl-1H-1,2,3-triazol-4-yl] quinoline (7b) with potassium [F-18] fluoride. At the end of synthesis, 1280-1830 MBq (n = 8) of [F-18]7a was obtained with >98% radiochemical purity and 118-237 GBq/mu mol specific activity using 3300-4000 MBq of [F-18]F . In vitro autoradiography showed that [F-18]7a had high specific binding with mGluR1 in the rat brain. Biodistribution study using a dissection method and small-animal PET showed that [F-18]7a had high uptake in the rat brain. The uptake of radioactivity in the cerebellum was reduced by unlabeled 7a and mGluR1-selective ligand JNJ-16259685 (2), indicating that [F-18]7a had in vivo specific binding with mGluR1. Because of a low amount of radiolabeled metabolite present in the brain, [F-18]7a may have a limiting potential for the in vivo imaging of mGluR1 by PET. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.048