J. Miller, E. Miller, Andg C Finger
Jun 1, 1957
Citations
0
Influential Citations
89
Citations
Quality indicators
Journal
Cancer research
Abstract
Summary A study of the carcinogenicities of various fluoro and other derivatives of 4-dimethylaminoazobenzene (DAB) in the rat liver has indicated that an unsubstituted 2-position in this dye is necessary for carcinogenic activity. The following compounds had moderate to strong carcinogenic activity: 3-fluoro-DAB, 3′,4′-difluoro-DAB, 2,5,2′,5′-tetrafluoro-DAB, 2′-methoxy-DAB, 3′-methoxy-DAB, 4′-methoxy-DAB, and 4′-ethyl-DAB. The following compounds had only weak carcinogenic activity: 3-methyl-DAB, 2-methyl-4-monomethylaminoazobenzene, and 3′,4′-dimethyl-DAB. The following compounds had no detectable carcinogenic activity: 2,6-difluoro-DAB, 2,6,3′,5′-tetrafluoro-DAB, 2,6,2′,4′,6′-pentafluoro-DAB, 3-hydroxy-DAB, DAB methochloride, 2-acetylamino-5-dimethylaminodiphenylamine, 2-nitro-5-dimethylaminodiphenylamine, 3,4-dinitrodimethylaniline, 4′-amino-4-dimethylaminodiphenylamine, 4′-imino-4-dimethylaminodiphenylimine sulfate, benzo[ c ]cinnoline, 2-dimethylaminobenzo[ c ]cinnoline, the dihydrochloride and N-acetyl derivative of N,N-dimethyl- p -phenylene diamine, aniline hydrochloride, N-acetyl m -toluidine, sodium p -dimethylaminobenzene diazonium sulfonate, and 4,4′-bis(dimethylamino)azobenzene. The syntheses of several new derivatives of DAB are described. These are 3-fluoro-, 2,6-difluoro-,3′,4′-difluoro-, 2,5,2′,5′-tetrafluoro-, 2,6,3′,-5′-tetrafluoro-, 2,6,2′,4′,6′-pentafluoro-, 3′-methoxy-, 4′-ethyl-, 3′,4′-dimethyl-, and 3-hydroxy-DAB.