5-(4-(123I)iodanylphenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole | 1256635-71-8

• 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-(123I)iodanylphenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole
• CAS: 1256635-71-8
• 化学式: C₁₇H₁₂F₃IN₂O₂S
• 分子量: 488.356
• InChiKey: NIUAGEVCVWHMTA-PIRNEEEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-(4-iodophenyl)-1-[4-(methylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole 在 四(三苯基膦)钯 、 六正丁基二锡 、 盐酸 、 sodium iodide 、 chloroamine-T 、 sodium iodide 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 为溶剂， 反应 16.07h， 生成 5-(4-(123I)iodanylphenyl)-1-(4-methylsulfonylphenyl)-3-(trifluoromethyl)pyrazole
  参考文献：
  名称：

  [¹²³I]-Celecoxib Analogues as SPECT Tracers of Cyclooxygenase-2 in Inflammation

  摘要：

  We report the synthesis and evaluation of a series of iodinated celecoxib analogues as cyclooxygenase-2 (COX-2)-targeted single photon emission computerized tomography (SPECT)-imaging agents for the detection of inflammation. The structure-activity relationship identified 5-(4-iodophenyl)-1-{4-(methylsulfonyl)-phenyl}-3-(trifuloromethyl)-1H-pyrazole (8) as a promising compound with IC50 values of 0.05 mu M against purified COX-2 and 0.03 mu M against COX-2 in activated macrophages. The arylstannane of 8-undergoes facile radio-[I-123]-iodination upon treatment with (NaI)-I-123/NaI and chloramine T using an EtOAc/H2O two-phase system. The [I-123]-8 was produced in a radiochemical yield of 85% and a radiochemical purity of 99%. In vivo SPECT imaging demonstrated that the radiotracer was taken up by inflamed rat paws with an average 1.7-fold enrichment over contralateral noninflamed paws. This study suggests that conversion of celecoxib into its isomeric iodo [I-123]-analogues is a useful approach for generating novel and efficacious agents for COX-2-targeted SPECT imaging of inflammation.

  DOI：

  10.1021/ml100232q