7,12-Dimethylbenz anthracene, biological

Yu, Q. and Degregorio, M.W. (2005) Ospemifene inhibits the growth of dimethylbenz anthracene-induced mammary tumors in Senear mice. The Journal of Steroid Biochemistry and Molecular Biology, 97, 230-240. 

Methods for the synthesis of the biologically active dihydrodiol and diol epoxide metabolites of both carcinogenic and noncarcinogenic polycyclic aromatic hydrocarbons are reviewed. Four general synthetic routes to the trans-dihydrodiol precursors of the bay region anti and syn diol epoxide derivatives have been developed. Syntheses of the oxidized metabolites of the following hydrocarbons via these methods are described benzo(a)pyrene, benz(a)anthracene, benzo-(e)pyrene, dibenz(a,h)anthracene, triphenylene, phen-anthrene, anthracene, chrysene, benzo(c)phenanthrene, dibenzo(a,i)pyrene, dibenzo(a,h)pyrene, 7-methyl-benz(a)anthracene, 7,12-dimethylbenz(a)anthracene, 3-methylcholanthrene, 5-methylchrysene, fluoranthene, benzo(b)fluoranthene, benzo(j)fluoranthene, benzo(k)-fluoranthene, and dibenzo(a,e)fluoranthene. 

Anti-thyroid activity. Boiled rice taken orally by adults at a dose of 350 g/person was inactive on iodine uptake by the thyroid Anti-tumor activity. Bran, administered intraperitoneally to mice at a dose of 100 mg/kg, was active on Sarcoma 180 (solid). The biological activity has been patented . Fermented grains, in the ration of rats, were active. Miso, a paste made from the seeds of Oryza sativa and G lycine max (soybean), was fed ad libitum. The incidence of cancers in the miso treated rats was 20% less than controls vs 7,12-dimethylbenz-[a]anthracene -induced carcinogenesis ". Water extract of dried seed hull, administered intraperitoneally to mice, was active on Sarcoma 180 (ASC). A glycoprotein fraction has been tested. The biological activity reported has been patented . Anti-ulcer activity. A cerebroside fraction of rice bran, administered intraperitoneally to mice at a dose of 100 mg/kg, was inac-... 

Anthracene and Related Compounds. The formation of anthracene by elimination of hydride from 9,10-dihydroanthracene has been reported in the preceding section. An improved high-yield synthesis of 7,12-dimethylbenz-[ajanthracene (336), a compound of biological interest, utilizes the reaction of 7,12-benz[a]anthraquinone with MeLi. Subsequent reaction with dry HCl in ethyl acetate produces 7-(chloromethyl)-12-methylbenz[a]anthracene, reduction of which gives (336). 

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