Metabolic N-hydroxylation of substituted acetophenone imines. I. Evidence for formation of isomeric oximes.
A series of chemically stable substituted acetophenone imines and their potential N-hydroxylated metabolites (i.e., oximes) have been synthesized and characterized by spectroscopic methods. The enzymic N-hydroxylation of acetophenone imines in vitro has been demonstrated as a general metabolic pathway in several mammalian species including the guinea-pig. The oxime metabolites were formed as mixtures of two geometric isomers, Z (syn-phenyl) and E (anti-phenyl), wherein the phenyl and hydroxyl group are cis and trans to each other respectively. The E (anti-phenyl) isomer was the quantitatively predominant isomeric form metabolically produced by all species studied. The relative proportions of the E and Z isomers in metabolic mixtures were found to be species dependent.
D000098:Acetophenones / Q000378:metabolism*; D000818:Animals; D002849:Chromatography, Gas; D006224:Cricetinae; D005289:Ferrets; D006168:Guinea Pigs; D006900:Hydroxylation; D007097:Imines / Q000378:metabolism*; D008297:Male; D008647:Mesocricetus; D051379:Mice; D008862:Microsomes, Liver / Q000201:enzymology; D010091:Oximes / Q000378:metabolism*; D011817:Rabbits; D051381:Rats; D011919:Rats, Inbred Strains; D013045:Species Specificity; D013237:Stereoisomerism
D000098:Acetophenones; D007097:Imines; D010091:Oximes