Synthesis and carcinogenic activity of oxidized benzacridines: potential metabolites of the strong carcinogen 7-methylbenz[c]acridine and of the inactive isomer 12-methylbenz[a]acridine.
The synthesis of 15 compounds related either to the benz[c]acridine or to the benz[a]acridine series is reported. Spectral data, i.e., NMR and EI fragmentation, are given. These compounds were tested for carcinogenic activity in mice of the XVIInc/Z strain by subcutaneous injection. Only three weak carcinogens were detected, 5,6-dihydro-5,6-dihydroxy-12-methylbenz[a]acridine, 3-methoxy-7-methylbenz[c]acridine, and 4-acetoxy-7-methylbenz[c]acridine. These results are discussed with consideration to the data previously obtained with other benzacridines and condensed quinolines.
D000166:Acridines / Q000138:chemical synthesis*; D000818:Animals; D002273:Carcinogens / Q000138:chemical synthesis*; D005260:Female; D007202:Indicators and Reagents; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008815:Mice, Inbred Strains; D009374:Neoplasms, Experimental / Q000139:chemically induced / Q000473:pathology; D012878:Skin Neoplasms / Q000139:chemically induced / Q000473:pathology; D013329:Structure-Activity Relationship
D000166:Acridines; D002273:Carcinogens; D007202:Indicators and Reagents; C037424:12-methylbenz(a)acridine; C031277:7-methylbenz(c)acridine