Journal Article

Synthesis and mutagenicity of some cyclopenta[<i>c</i>]phenanthrenes and indeno[<i>c</i>]phenanthrenes

Assunta Marrocchi, Lucio Minuti, Guido Morozzi, Lucia Pampanella and Aldo Taticchi

in Carcinogenesis

Volume 17, issue 9, pages 2009-2012
Published in print September 1996 | ISSN: 0143-3334
Published online September 1996 | e-ISSN: 1460-2180 | DOI:
Synthesis and mutagenicity of some
                    cyclopenta[c]phenanthrenes and

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An efficient two-step synthesis of 8(H)-9,10,11,12-tetrahydrodicyclopenta[a,c]phenanthren-7-one, based on the high pressure Diels-Alder cycloaddition of 4-acetoxy-2-cyclopenten-1-one with1-(1-naphthyl)cyclopentene and a subsequent dehydrogenation-aromatization reaction, is reported. Further, the synthesis of two cyclopenta[c]-phenanthrenes and indeno[c] phenanthrenes is described. Structural analysis of the new products by 1H and 13C NMR spectroscopy is presented. The mutagenic activity of the compounds in Salmonella typhimurium was estimated by Ames' test. Three compounds were shown to be mutagenic for the strain TA 100. The mutagenic activities exhibited by cyclopenta[c]phenanthrenes are compared with those shown by the related cyclopenta[a]phenanthrenes and then discussed with respect to the effect of the cyclopentane ring facing the bay region. Indeno[c]phenanthrenes are mostly inactive. The effect of benzoannulation on the mutagenic activities of cyclopenta[c]phenanthrenes is discussed.

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Subjects: Clinical Cytogenetics and Molecular Genetics

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