- Synthesis of dibenzo[def,p]chrysene, its active metabolites, and their 13C-labeled analogues
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Dibenzo[def,p]chrysene (DBC) Is a highly carcinogenic polycyclic aromatic hydrocarbon suspected to be Involved in initiation of lung cancer in smokers. Efficient new syntheses of DBC, Its active metabolites [DBC diol (1), DBC dione (2), DBC diol epoxlde (3)], and their previously unknown 13C 2-labeled analogues are reported. The 13C 2-labeled analogues are required as standards for sensitive methods of analysis of their DNA adducts in human cells using stable isotope dilution liquid chromatography/tandem mass spectrometry.
- Xu, Daiwang,Duan, Yazhen,Blair, Ian A.,Penning, Trevor M.,Harvey, Ronald G.
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supporting information; experimental part
p. 1059 - 1062
(2009/04/06)
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- A highly abbreviated synthesis of dibenzo[def,p]chrysene and its 12-methoxy derivative, a key precursor for the synthesis of the proximate and ultimate carcinogens of dibenzo[def,p]chrysene
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Dibenzo[def,p]chrysene (DBC) (1), is by far the most mutagenic and toxic polycyclic aromatic hydrocarbon identified. Its metabolic activation leads to trans-11,12-dihydroxy-11,12-dihydro-DBC (2), which is further metabolized to the ultimate metabolite, anti-trans-11,12-dihydroxy-13,14-epoxy-11,12,13,14-tetrahydro-DBC (3), that binds to DNA causing mutations and ultimately tumor induction. We report a facile route for the syntheses of DBC (1) and its 12-methoxy derivative (12-methoxy-DBC) (13), a key intermediate for the synthesis of 2 and 3, using a Suzuki cross-coupling approach.
- Sharma, Arun K.,Kumar, Subodh,Amin, Shantu
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p. 3979 - 3982
(2007/10/03)
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