Carcinogenic Activity of Analogues of p-Dimethylaminoazobenzene. IV. Activity of the Quinoline Analogues 2
Ellis V. Brown, Robert M. Novack, Ali A. Hamdan
Abstract
Ellis V. Brown, Robert M. Novack, Ali A. Hamdan
Abstract
Thirteen isomers of the p-dimethylaminophenylazoquinolines and their corresponding N-oxides were investigated for hepatic carcinogenic activity in Sprague-Dawley rats. The dyes were all fed at the 0.03 percent level, and the more active isomers were also examined at the 0.01 percent level. The isomers are listed in order of decreasing activity, with semiquantitative values based on p-dimethylaminoazobenzene as 6: 6- (p- dimethylaminophenylazo)quinoline, 200+ ; 5-(p-dimethylaminophenylazo)quinoline-1-oxide, 200+; 5-(p-dimethylaminophenylazo)quinoline, 150; 6-(p-dimethylaminophenylazo)quinoline-1-oxide, 100; 4-(p-dimethylaminophenylazo)quinoline-1-oxide, 22; 4-(p-dimethylaminophenylazo)quinoline, 15; 3- (p-dimethylaminophenylazo)quinoline-1-oxide, 3-(p-dimethylaminophenylazo)quinoline, 7-(p-dimethylaminophenylazo)quinoline-1-oxide, 7-(p-dimethylaminophenylazo)quinoline, 8-(p-dimethylaminophenylazo)quinoline-1-oxide, 8-(p-dimethylaminophenylazo)quinoline, and 2-(p-dimethylaminophenylazo)quinoline-1-oxide, with all the latter less than 2.
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Thirteen isomers of the p-dimethylaminophenylazoquinolines and their corresponding N-oxides were investigated for hepatic carcinogenic activity in Sprague-Dawley rats. The dyes were all fed at the 0.03 percent level, and the more active isomers were also examined at the 0.01 percent level. The isomers are listed in order of decreasing activity, with semiquantitative values based on p-dimethylaminoazobenzene as 6: 6- (p- dimethylaminophenylazo)quinoline, 200+ ; 5-(p-dimethylaminophenylazo)quinoline-1-oxide, 200+; 5-(p-dimethylaminophenylazo)quinoline, 150; 6-(p-dimethylaminophenylazo)quinoline-1-oxide, 100; 4-(p-dimethylaminophenylazo)quinoline-1-oxide, 22; 4-(p-dimethylaminophenylazo)quinoline, 15; 3- (p-dimethylaminophenylazo)quinoline-1-oxide, 3-(p-dimethylaminophenylazo)quinoline, 7-(p-dimethylaminophenylazo)quinoline-1-oxide, 7-(p-dimethylaminophenylazo)quinoline, 8-(p-dimethylaminophenylazo)quinoline-1-oxide, 8-(p-dimethylaminophenylazo)quinoline, and 2-(p-dimethylaminophenylazo)quinoline-1-oxide, with all the latter less than 2.
Key concepts: Quinoline, Chemistry, Medicinal chemistry, Oxide, Organic chemistry