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One‐step, no‐carrier‐added, synthesis of a 18 F‐labelled benzodiazepine receptor ligand
Author(s) -
Jalilian Amir Reza,
Tabatabai Sayyed Abbas,
Shafiee Abbas,
Afarideh Hossein,
Najafi Reza,
Bineshmarvasti Maria
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(200005)43:6<545::aid-jlcr340>3.0.co;2-1
Subject(s) - chemistry , trifluoromethanesulfonate , fluoride , ligand (biochemistry) , yield (engineering) , oxadiazole , chemical synthesis , medicinal chemistry , nitrile , solvent , fluorine , nuclear chemistry , benzodiazepine , tetrabutylammonium fluoride , radiochemistry , organic chemistry , receptor , inorganic chemistry , catalysis , in vitro , biochemistry , materials science , metallurgy
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‐18 (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°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. Copyright © 2000 John Wiley & Sons, Ltd.