Synthesis and structure--mutagenicity relationship of benzo-annulated cyclopentaphenanthrenes.
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 (1)H and (13)C NMR spectroscopy is presented. Estimates of the mutagenic activity of compounds 2--4, 6 and 11--14 in Salmonella typhimurium determined by Ames' 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.
Marrocchi
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Dipartimento di Chimica, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy.
Minuti
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Morozzi
G
G
Taticchi
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D004305:Dose-Response Relationship, Drug; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009152:Mutagenicity Tests; D009153:Mutagens / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010616:Phenanthrenes / Q000737:chemistry; D012486:Salmonella typhimurium / Q000187:drug effects / Q000235:genetics; D013329:Structure-Activity Relationship
D006841:Hydrocarbons, Aromatic; D009153:Mutagens; D010616:Phenanthrenes