Bioreductively-activated prodrugs for targeting hypoxic tissue: Elimination of aspirin from 2-nitroimidazole derivatives

Article abstract of DOI:10.1016/S0960-894X(99)00171-7

2-Nitroimidazoles were synthesised substituted with aspirin or salicylic acid, as leaving groups linked through the (imidazole-5-yl)methyl position. Activation of aqueous solutions by CO₂^- (a model one-electron reductant) resulted in release of aspirin or salicylate, probably via the 2- hydroxyaminoimidazole. The analogous 2-nitroimidazole with bromide as leaving group eliminated bromide in <1 ms via radical-anion.