[18F]-5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-fluorobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [18F]-5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-fluorobenzoate
• 英文别名: [5-(2-phenoxyphenyl)-1,3,4-oxadiazol-2-yl] 4-(18F)fluoranylbenzoate
• 化学式: C₂₁H₁₃FN₂O₄
• 分子量: 375.345
• InChiKey: BRKHLQJZZVSYKF-KVTPGWOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Trifluoromethanesulfonate;trimethyl-[4-[[5-(2-phenoxyphenyl)-1,3,4-oxadiazol-2-yl]oxycarbonyl]phenyl]azanium 在 potassium [¹⁸F]fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 生成 [18F]-5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl 4-fluorobenzoate
  参考文献：
  名称：

  One-step, no-carrier-added, synthesis of a18F-labelled benzodiazepine receptor ligand

  摘要：

  5-(2-Phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-fluorobenzoate, a non-classical benzodiazepine receptor ligand, has shown anticonvulsant activity against pentylenetetrazole-induced convulsion. In order to perform biological studies, we decided to label the compound with positron-emitting fluorine-ls (t(1/2)=109.7 min). The latter compound was prepared in no-carrier-added form from [(18)F]fluoride and 5-(2-phenoxy)phenyl-1,3,4-oxadiazole-2-yl-4-N,N,N-trimethylanilinium triflate in one step. The best results were obtained using Kryptofix2.2.2/[(18)F]fluoride with dimethylsulfoxide as the solvent at 90 degrees C. Column chromatography afforded the desired compound in 15 min in an overall radiochemical yield of 70-75% corrected to the end of radionuclide production with a specific radioactivity of about 3000 Ci/mmol and a radiochemical purity of more than 95% and high chemical purity.

  DOI：

  10.1002/(sici)1099-1344(200005)43:6<545::aid-jlcr340>3.0.co;2-1