EFFICIENT NEW SYNTHESES OF POLYCYCLIC AROMATIC HYDROCARBON ORTHO-QUINONES AND THEIR 2′-DEOXYRIBONUCLEOSIDE ADDUCTS |
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Authors: | Ronald G Harvey Qing Dai Chongzhao Ran Sridhar R Gopishetty Trevor M Penning |
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Affiliation: | 1. The Ben May Institute for Cancer Research, University of Chicago , Chicago, Illinois, USA;2. Department of Pharmacology, School of Medicine, University of Pennsylvania , Philadelphia, Pennsylvania, USA |
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Abstract: | Three mechanisms have been proposed to explain the carcinogenic activities of polycyclic aromatic hydrocarbons (PAHs). On the basis of the nature of the active metabolites involved, they may be termed: the diol epoxide mechanism, the quinone mechanism, and the radical-cation mechanism. In connection with studies to evaluate the relative importance of these pathways, we required practical methods for the syntheses of the active PAH metabolites involved. We now report efficient new synthesis of the o-quinones of benzoa]pyrene (BPQ), 7,12-dimethylbenza]anthracene (DMBAQ), and benza]anthracene (BAQ). These quinones are convenient synthetic precursors of the related o-catechols, trans-dihydrodiols, and diol epoxides, as well as the stable adducts of the o-quinones with 2-deoxyadenosine and 2′-deoxyguanosine. |
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Keywords: | Synthesis of PAH o-quinones benzo[a]anthracene benzo[a]- pyrene 7 12-dimethbenz[a]anthracene PAH-deoxyribonucleoside adducts Suzuki coupling |
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