Journal of Medicinal Chemistry p. 1156 - 1161 (1984)
Update date:2022-07-29
Topics:
Chou, M. W.
Heflich, R. H.
Casciano, D. A.
Miller, D. W.
Freeman, J. P.
et al.
The mutagenic environmental pollutants 1-, 3-, and 6-nitrobenzopyrene were synthesized.Nitration of 7,8,9,10-tetrahydrobenzopyrene with sodium nitrate in trifluoroacetic acid and acetic anhydride at ambient temperature gave a mixture of 1-, 3-, and 6-nitro-7,8,9,10-tetrahydrobenzopyrene, which was separated by chromatography.Dehydrogenation of the isolated nitrotetrahydrobenzopyrenes with 2,3-dichloro-4,5-dicyano-1,6-benzoquinone produced 1-, 3-, and 6-nitrobenzopyrene in high yield.Comparison of the spectral data of these compounds with those obtained from direct nitration of benzopyrene confirmed that 1- and 3-nitrobenzopyrenes are indeed the minor products of the latter reaction.This confirmation also verifies that 1- and 3-nitrobenzopyrene were the minor nitrated products of benzopyrene formed in model air atmospheres.The 1-, 3-, and 6-nitrobenzopyrene were mutagenic in Salmonella typhimurium tester strains TA98 and TA100 in the presence of a mammalian microsomal (S9) activating system.Both 1- and 3-nitrobenzopyrene, but not 6-nitrobenzopyrene, were also direct-acting mutagens in these strains.However, only 6-nitrobenzopyrene exhibited weak mutagenic activity when tested in Chinese hamster ovary cells, while only 3-nitrobenzopyrene produced a concentration-dependent decrease in cellular survival.
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