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On the Enhancement of the Carcinogenicity of 4-Dimethylaminoazobenzene by Fluoro-Substitution^*

( McArdle Memorial Laboratory, Medical School, University of Wisconsin, Madison, Wis., and the Division of Fluorine Chemistry, Illinois State Geological Survey, Urbana, Ill.)

In an investigation on the importance of the ring positions of 4-dimethylaminoazobenzene to its carcinogenic activity, the following new compounds were synthesized and tested in the rat: 2-fluoro-, 2',4'-difluoro-, 2',5'-difluoro-, 3',5'-difluoro-, and 2',4',6'-trifluoro-4-dimethylaminoazobenzene. All these compounds were found to be more active liver carcinogens than the parent dye. The same finding had been made previously for the 2'-, 3'-, and 4'-fluoro derivatives. On the basis of these results it appears that no position on the prime ring of 4-dimethylaminoazobenzene is directly concerned in the carcinogenic process. The other ring remains to be investigated by this method.

The results further suggest that the effects of systematic fluoro-substitution on the activities of other biologically active molecules could furnish strong evidence on which positions do or do not contribute directly to the activity in question.

^* This investigation was supported in part by grants from the National Cancer Institute, U.S. Public Health Service, and the Alexander and Margaret Stewart Trust Fund.

Received 10/11/52.