Relationship between resonance energy and carcinogenic activity of benz[c]acridines.
In order to investigate the correlation between the carcinogenic activity of benz[c]acridines and the electron density, the Huckel orbital method was used. Resonance energies, circuit resonance energies and bond currents of benz[c]acridines were calculated by Aihara's TRE theory. It was shown that these compounds had very stable aromatic characters with positive resonance energies and that the resonance energies per pi-electron values for the compounds with lack of the double bond corresponding to the K-region from the parent skeleton were more stable than those of their parent compounds. 7-Methyl-benz[c]acridine derivatives with the methyl groups at 7-, 7, 9-, 7, 10-, 7, 11-, 7, 9, 10-, or 7, 9, 11-positions except 5, 7-dimethylbenz[c]acridine had potent carcinogenic activity and significantly lower resonance energy per pi-electron.
Motohashi
N
N
Department of Medicinal Chemistry, Meiji College of Pharmacy, Tokyo, Japan.
Kurihara
T
T
Sakagami
H
H
Molnar
J
J
D000166:Acridines / Q000737:chemistry* / Q000633:toxicity; D000818:Animals; D002273:Carcinogens / Q000737:chemistry* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000166:Acridines; D002273:Carcinogens; C035985:benz(c)acridine