title: Structure-activity relationships of alpha, beta-unsaturated carbonylic compounds.
abstract: The mutagenicity and probably the carcinogenicity of alpha, beta-unsaturated carbonylic compounds such as acrolein are based on direct genotoxic interaction with nucleic acid bases via Michael addition or Schiff's base formation. Alkyl and aryl substitution at the alpha and beta carbon atoms reduces or abolishes the mutagenic potential whereas halogen substitution in either position increases mutagenicity. These structure-activity relationships can be predicted from theoretical considerations of well-known electron shift mechanisms. The formation of alpha, beta-unsaturated carbonyls from allylic halides (or similar types of compounds with appropriate leaving groups) has been experimentally demonstrated with appropriate metabolites of allyl bromide in in rats.
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives / Q000633:toxicity*; D000447:Aldehydes / Q000633:toxicity*; D000498:Allyl Compounds / Q000633:toxicity*; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000187:drug effects; D004249:DNA Damage; D006846:Hydrocarbons, Halogenated; D009152:Mutagenicity Tests; D009153:Mutagens; D012486:Salmonella typhimurium / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000447:Aldehydes; D000498:Allyl Compounds; D006846:Hydrocarbons, Halogenated; D009153:Mutagens; D000171:Acrolein; D004247:DNA