Synthesis of a Sterically Impeded Analogue of the Carcinogenic Anti Diol Epoxide Metabolite of Benzo[a]pyrene

Journal of Organic Chemistry

Volumn 52, Issue 11, 1987, Pages 2226-2230

  Pataki, John ^a   Harvey, Ronald G ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGEN;

DNA BINDING; METABOLIC ACTIVATION; METHODOLOGY; NONHUMAN; SYNTHESIS;

EID: 0023259701     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00387a023     Document Type: Article

References (22)

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3. Harvey, R. G. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symp. Series No. 283; American Chemical Society: Washington DC, 1985.
4. Weinstein, I. B.; Jeffrey, A. M.; Jennette, K. W.; Blobstein, S. H.; Harvey, R. G.; Harris, C.; Autrup, H.; Kasai, H.; Nakanishi, K. Science (Washington D. C.) 1976, 193, 592.
5. Jeffrey, A. M.; Weinstein, I. B.; Jennette, K. W.; Grzeskowiak, K.; Nakanishi, K.; Harvey, R. G.; Autrup, H.; Harris, C. Nature (London) 1977, 269, 348.
6. Jeffrey, A. M.; Jennette, K. W.; Blobstein, S.; Weinstein, I. B.; Beland, F. A.; Harvey, R. G.; Kasai, H.; Muira, I.; Nakanishi, K. J. Am. Chem. Soc. 1976, 98, 5714.
7. Geacintov, N. E.; Yoshida, H.; Ibanez, V.; Harvey, R. G. Biochemistry 1982, 21, 1864.
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9. Harvey, R. G.; Osborne, M. R.; Connell, J. R.; Venitt, S.; Crofton-Sleigh, C.; Brookes, P.; Pataki, J.; DiGiovanni, J. In The Role of Chemicals and Radiation in the Etiology of Cancer, Carcinogenesis: Huberman, E.; Barr, S. H., Eds.; Raven Press: New York, 1985; Vol. 10, pp 449–464.
10. This transformation is most efficiently achieved in the case of the unsubstituted parent BP compound by reaction with 2,3-dichloro-5,6-dicyanoL,4-benzoquinone (DDQ) in refluxing benzene: Harvey, R. G.; Fu, P. In Polycyclic Hydrocarbons and Cancer: Gelboin, H. V., Ts'o, P. 0. P., Eds.; Academic Press: New York, 1978; pp 133–165.
11. Review: Harvey, R. G. Synthesis 1986. 605.
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