- Synthesis of Cyclopentanobenzanthracene Compounds Related to Carcinogenic Benzanthracene and Cholanthrene Hydrocarbons
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Syntheses of benzaceanthrylene (4a), 8-methylbenzaceanthrylene (4b), and their 1,2-dihydro derivatives (3a,b), as well as 6-methylbenzaceanthrylene (5a) and its 1,2-dihydro derivative (2b) from benzanthracene-7,12-dione are described.Compounds 2b, 3b, 4b, and 5b, all of which contain a methyl group in nonbenzo bay region position, are predicted to be relatively potent carcinogens.
- Lee, Hongmee,Harvey, Ronald G.
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p. 3787 - 3791
(2007/10/02)
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- Synthesis and carcinogenic activity of 5-fluoro-7-(oxygenated methyl)-12-methylbenz[a]anthracenes
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Treatment of 7,12-benz[a]anthraquinone(2) with methylmagnesium iodide or methyllithium yields mixtures of cis- and trans-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (3a,b), in which the ratio of cis to trans lies in the 3-4:1 region. Each isomer afforded high yields of 7-chloromethyl-12-methylbenz[a]anthracene (5) on treatment with hydrogen chloride in ethyl acetate. Similarly, 5-fluoro-7,12-benz[a]anthraquinone (8) afforded a mixture of cis- and trans-5-fluoro-7,12-dihydro-7,12-dihydroxy-7,12-dimethylbenz[a]anthracenes (9) which yielded 7-chloromethyl-5-fluoro-12-methylbenz[a]anthracene (10) on treatment with HCl. The chloromethyl compounds, 5 and 10, yielded 7-acetoxymethyl-12-methylbenz[a]anthracene (6) and 7-acetoxymethyl-5-fluoro-12-methylbenz[a]anthracene (11) on treatment with acetate ion. Hydrolysis of 6 and 11 yielded 7-hydroxymethyl-12-methylbenz[a]anthracene (7) and 5-fluoro-7-hydroxymethyl-12-methylbenz[a]anthracene (12), respectively. Since neither 11 nor 12 is appreciably carcinogenic, the carcinogenic metabolism of 7,12-dimethylbenz[a]anthracene (DMBA) probably does not involve attack at the 7-methyl group.
- Newman,Fikes,Hashem,Kannan,Sankaran
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p. 1076 - 1078
(2007/10/13)
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