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Mlany polycyclic aromatic hydrocarbons and aromatic amines share in common the ability to evoke cancer in certain animal species; the most powerful of these carcinogens is 7,12-dimethylbenz(a)anthracene.1 A single pulse dose of 7,12DMIBA evokes mammary cancer invariably and rapidly in Sprague-Dawley rats; the yield of cancers per rat is greatly enhanced when several pulse-doses are given at intervals of a few days.2 In addition to evoking cancer in a dramatic way, 7,12-DMBA causes massive hormone-dependent necrosis of two zones of the rat's adrenal;3 this effect is only exerted by congeners whose structure is very closely related to 7,12-DIMBA. It has been found that adrenocorticolysis of this special sort can be prevented by any of a large number of cyclic compounds,4-6 provided that it is given prior to 7,12DMBA. Prevention of hydrocarbon-induced adrenal apoplexy is useful as a rapid screen to identify compounds which also will suppress aromatic-induced cancer. 2 In the present work, series of aromatic azo and ethylene derivatives were investigated for their ability to induce protection against adrenal injury and cancer induced by 7,12-DMBA. The most effective inducers in this regard were found to be 1-(p-phenylazo-phenylazo)-2-naphthol (sudan III) and compounds closely related to it; these exceed by an order of magnitude all protectors that have been described earlier. Moreover, dose-response in the induction of an enzyme, menadione reductase, runs in parallel with efficacy of azo dyes in the induction of adrenal protection. Experimental.-Chemical: Some of the compounds were purchased and these were recrystallized from appropriate solvents. Compounds IV, VI, VII, X-XII, XIV-XIX, XXI, XXIVXXXV, XXXVII-XLII, were synthesized by known procedures and purified by chromatography. Compounds VIII and IX, the d-, 1-, and mesoforms of 1,1'-azotetralin were prepared by the ollowing reaction scheme:

AROMATIC AZO DERIVATIVES PREVENTING MAMMARY CANCER AND ADRENAL INJURY FROM 7,12-DIMETHYLBENZ(a)ANTHRACENE