72648-44-3Relevant academic research and scientific papers
Synthesis of the Angular Ring Tetrahydro Epoxides of the Carcinogens 7- and 12-Methylbenzanthracene and 7,12-Dimethylbenzanthracene
Lehr, Roland E.,Kole, Panna L.,Singh, Mahatam,Tschappat, Kathryn D.
, p. 850 - 857 (2007/10/02)
Tetrahydro epoxide derivatives at the 1,2-and 3,4-positions on the angular ring of carcinogens 7- and 12-methylbenzanthracene (7- and 12-MeBA) and 7,12-dimethylbenzanthracene (7,12-DMBA) have been synthesized in order to probe the basis for the tumorigenicity-enhancing effects of methyl groups on polycyclic aromatic hydrocarbons (PAH).The epoxides were prepared from the corresponding dihydro PAH.For the 7-MeBA and 12-MeBA derivatives, access to the dihydro derivatives was achieved by acetoxylation at the 1- and 4-positions of the tetrahydro ring of 7-and 12-acetoxy-1,2,3,4-tetrahydrobenzanthracene, respectively (Scheme II).For the 7,12-DMBA derivatives, oxidation of 1,2,3,4-tetrahydrobenzanthracene-7,12-quinone afforded the 1- and 4-oxo derivatives, which were converted to the respective dihydro compounds (Scheme III).Alkenes 13 and 22, both of which have a 12-methyl group and C1-C2 double bond, were higly susceptible to endoperoxide formation.The dihydro compounds were converted to the epoxides via cyclization of the bromohydrin or bromoacetate derivatives (Scheme IV).The 1,2-bromohydrin and/or bromoacetate derivatives of 3,4-dihydro-12-methylbenzanthracene and 3,4-dihydro-7,12-dimethylbenzanthracene were highly labile and required special handling in order to be purified and converted into the epoxide derivatives.
Synthesis and Mutagenicity of A-Ring Reduced Analogues of 7,12-Dimethylbenzanthracene
Inbasekaran, Muthiah N.,Witiak, Donald T.,Barone, Karen,Loper, John C.
, p. 278 - 281 (2007/10/02)
The synthesis and mutagenicity of two derivatives of 7,12-dimethylbenzanthracene (DMBA; 1), i.e., 1,2-H2DMBA (4) and 1,2,3,4-H4DMBA (5), are reported.These analogues (4 and 5) represents dihydro and tetrahydro A-ring reduced forms of DMBA, a region in the parent hydrocarbon (1) proposed to be involved in metabolism to the ultimate carcinogen.The synthesis for 4 without isolation of intermediates from the tosylhydrazone of 1,2,3,4-tetrahydrobenzanthracene-4,7,12-trione (10) by successive reaction with 8 molar equiv of CH3Li, HI, and NaBH4 represents a novel approach to this hydrocarbon now available in sufficient quantity for biological studies.Interestingly, both of these reduced analogues 4 and 5 exhibited mutagenic activity in the Ames assay in the presence or absence of microsomal activation for strains TA98 and TA100.In these strains, DMBA was active only in the presence of S-9 fraction.In the plasmid-deficient strain TA1537, only tetrahydro analogue 5 exhibited mutagenic activity both in the absence and presence of S-9 fraction.
