Journal of Medicinal Chemistry p. 546 - 549 (1991)
Update date:2022-08-04
Topics:
Sangaiah
Gold
Newcomb
Ball
The possibility of bay-region activation of the cyclopenta PAH (polycyclic aromatic hydrocarbon with a peripherally fused cyclopenta ring) benz[j]aceanthrylene (1) was investigated by synthesis and bioassay of the bay-region metabolites trans-9,10-dihydroxy-9,10-dihydrobenz[j]aceanthrylene (4), trans-9,10-dihydroxy-anti-7,8-epoxy-7,8,9,10-tetrahydrobenz[j] aceanthrylene (2), and 9,10-dihydrobenz[j]aceanthrylene 9,10-oxide (3). The known 1,2-dihydrobenz[j]aceanthrylene-9,10-dione (5) was obtained by published methods; however, the direct route to target dihydrodiol 4, dehydrogenation of the saturated five-membered ring of 5 followed by NaBH4 reduction, gave a poor yield of 4 contaminated with tetrahydrogenated products. Acceptable yields of 4 were obtained by reduction of 5 to the corresponding tetrahydro diol, diacetylation of the diol, and dehydrogenation of the five-membered ring followed by base-catalyzed deacetylation to 4. anti-Diol epoxide 2 was generated by m-chloroperoxybenzoic acid oxidation of 4. Oxide 3 was synthesized by treatment of the monotosylate of 4 with NaOH in monoglyme. Diol epoxide 2 was an active mutagen in Salmonella typhimurium strain TA98 in the absence of metabolic activation, 3 showed marginal activity, while 3 and 4 were mutagenic with metabolic activation. These results coupled with previous studies support activation of benz[j]aceanthrylene via both 2 and cyclopenta ring epoxidation.
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