title: Non-mutagenic nitroheterocycles. The lack of correlation between bacterial mutagenicity and one-electron reduction potential.
abstract: The bacterial mutagenicity (Ames test) and the one-electron reduction potential for several nitropyridines, nitropyrazines and nitropyrimidines were determined. It was found that, although these nitroheterocycles underwent one-electron reduction more easily than metronidazole, they were not mutagenic in the Ames test. Six-membered ring nitroheterocycles, will, in general, exhibit diminished mutagenic potential compared to five-membered ring nitroheterocycles, and it is postulated that this effect is due to differences in the electronic nature and potential chemical reactivity of their respective nitrenium ions.
mesh_terms: D004583:Electrons; D009152:Mutagenicity Tests; D009153:Mutagens / Q000633:toxicity*; D009154:Mutation; D010084:Oxidation-Reduction; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D009153:Mutagens