Synthesis and structure--mutagenicity relationship of benzo-annulated cyclopentaphenanthrenes

Bioorg Med Chem. 2001 Jun;9(6):1509-15. doi: 10.1016/s0968-0896(01)00036-0.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dose-Response Relationship, Drug
  • Hydrocarbons, Aromatic / chemical synthesis
  • Hydrocarbons, Aromatic / chemistry*
  • Hydrocarbons, Aromatic / pharmacology*
  • Mutagenicity Tests
  • Mutagens / chemical synthesis
  • Mutagens / chemistry*
  • Mutagens / pharmacology*
  • Phenanthrenes / chemistry
  • Salmonella typhimurium / drug effects
  • Salmonella typhimurium / genetics
  • Structure-Activity Relationship

Substances

  • Hydrocarbons, Aromatic
  • Mutagens
  • Phenanthrenes