Abstract
In previous studies of the metabolism of the ubiquitous air pollutant 3-nitrofluoranthene (3-NF) in this laboratory, the major urinary metabolites seen 8–24 hours after administration of radiolabelled 3-NF to the rat have been tentatively identified by 1H-NMR as 3-amino-4,8-dihydroxyfluoranthene, 3-amino-4,9-dihydroxy-fluoranthene, and 3-amino-4,8,9-trihydroxyfluoranthene. In order to definitively identify and characterize the metabolites, each of the possible metabolites was synthesized. The dihydroxy substitution pattern must be established on fluoranthene prior to nitration, due to the deactivating effects of nitro groups. The 4,8-dihydroxy substitution pattern was established by Friedel-Crafts reaction, followed by oxidation and hydrolysis. The 8,9-dihydroxy and 4,8,9-trihydroxy substitution patterns were established by acetylation of 8-methoxyfluoranthene, followed by replacement of the methyl group with an acetyl group and oxidation of the acetyl functions. The 4,9-dihydroxy substitution pattern was established by initially brominating fluoranthene, followed by conversion of the dibromide to a diacetyl, nitration, oxidation and hydrolysis.
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