117696-92-1Relevant articles and documents
Bioactivation of the carcinogen 11-methoxy-16,17-dihydro-15H-cyclopenta[a]phenanthrene
Catterall, Fenton S.,Coombs, Maurice M.,Ioannides, Costas,Walton, Kim
, p. 85 - 90 (2000)
The title compound is a more potent carcinogen than would be anticipated from its simple phenanthrene structure lacking further D-ring conjugation. In vitro it undergoes microsomal metabolism to yield as major metabolites its 15- and 17-alcohols and its 16,17-diol; other minor metabolites are also derived from attack at the 5-membered ring, but no evidence of aromatic oxidation is apparent. The title compound is a weak mutagen in the Ames' test with Salmonella typhimurium TA100, but only with microsomal bio-activation. The 17-ol and 16,17-diol are inactive, with or without biological activation. By contrast the 15-alcohol, a rather reactive compound, is a strong mutagen both in the presence and absence of the bio-activation system. This, therefore, may be the proximate carcinogen, and its structural analogy to the naturally occurring hepato-carcinogen safrole is noted. Copyright (C) 2000 Elsevier Science B.V.
Potentially Carcinogenic Cyclopentaphenanthrenes. Part 12. Synthesis of Metabolites of the Carcinogen 16,17-Dihydro-11-methoxy-15H-cyclopentaphenanthrene
Coombs, Maurice M,Boyd, Gary W.
, p. 2901 - 2911 (2007/10/03)
Starting with 15,16-dihydro-11-methoxycyclopentaphenanthren-17-one, the isomeric 15- and 16-keto analogues have been synthesized along with all three isomeric secondary alcohols, the 16,17-trans-diol, and a number of other derivatives. Several of these compounds occur as metabolites of the title methoxy hydrocarbon. 16-Bromo-11-methoxycyclopentaphenanthren-17-one resists dehydrobromination to the corresponding 15(16)-en-17-one, a reaction which proceeds readily with the 16-bromides of the unsubstituted- and 11-methyl-17-ketones.
