Synthesis and structure–mutagenicity relationship of benzo-annulated cyclopentaphenanthrenes Original Research Article

The synthesis of 2,3-dihydro-1H-indeno[5,4-a]anthracene (2), the fluoreno[a]anthracenes 3 and 4, 2,3-dihydro-1H-cyclopenta[a]chrysene (6), 3,4-dihydro-2-vinylphenanthrene (10) and cyclopenta[c]chrysenes 11, 12 has been described. Structure analysis of the new products by 1H and 13C NMR spectroscopy is presented. Estimates of the mutagenic activity of compounds 2–4, 6 and 11–14 in Salmonella typhimurium determined by Amesʹ test indicate that all products are inactive for both TA 98 and TA 100 strains except 4,5-dihydro-3H-cyclopenta[c]chrysene (12). The mutagenic properties of these compounds have been compared with those shown by previously studied benzo[g]cyclopenta[a]phenanthrenes and cyclopenta[c]phenanthrenes and discussed. Some conclusions have been drawn about the effects of benzoannulation and of the carbonyl function on the mutagenicity of this class of compounds.