Copper-Mediated Radiobromination of (Hetero)Aryl Boronic Pinacol Esters
Jason C. Mixdorf, Sabrina Hoffman, Eduardo Aluicio‐Sarduy, Todd E. Barnhart, Jonathan W. Engle, Paul A. Ellison
Abstract
A copper-mediated radiobromination of (hetero)aryl boronic pinacol esters is described. Cyclotron-produced [ 76/77 Br]bromide was isolated using an anion exchange cartridge, wherein the pre-equilibration and elution solutions played a critical role in downstream deboro-bromination. The bromination tolerates a broad range of functional groups, labeling molecules with ranging electronic and steric effects. Bologically active radiopharmaceuticals were synthesized, including two radiobrominated inhibitors of poly ADP ribose polymerase, a clinically relevant chemotherapeutic target for ovarian, breast, and prostate cancers.
Topics & Concepts
ChemistryHalogenationArylPinacolSteric effectsBromideIodideCombinatorial chemistryCopperMedicinal chemistryOrganic chemistryCatalysisAlkylCancer Treatment and PharmacologyRadiopharmaceutical Chemistry and ApplicationsPARP inhibition in cancer therapy