Synthesis of new hypoxia markers EF1 and [F-18]-EF1

We report on the preparation of a hypoxia marker 2-(2-nitroimidazol-1[H]-yl )-N-(3-fluoropropyl)acetamide (EF1) and its F-18 analog, 2-(2-nitroimidazol -1[H]-yl)-N-(3-[F-18]fluoropropyl)acetamide ([F-18]-EF1). Two methods for t he preparation of 3-fluoropropylamine, the EF1 side chain, are described. [ F-18]-EF1 was prepared with a radiochemical yield of 2% by nucleophilic sub stitution of bromine in 2-(2-nitroimidazol-1[H]-yl)-N-(3-bromopropyl) aceta mide (EBrl) by carrier-added F-18 in DMSO at 120 degrees C. Our results demonstrate the preparation of clinically relevant amounts of [ F-18]-EF1 for use as a non-invasive hypoxia marker with detection using pos itron emission tomography (PET). (C) 1999 Elsevier Science Ltd. All rights reserved.