Synthesis of higher oxidized metabolites of dibenz[a,j]anthracene implicated in the mechanism of carcinogenesis

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8125-8132

  Zhang, Jin Tao ^a   Dai, Wei ^a   Harvey, Ronald G ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; CARCINOGEN; DIBENZ[A,J]ANTHRACENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DECHLORINATION; OXIDATION; PHOTOREACTIVITY; REACTION ANALYSIS; TOXIN SYNTHESIS;

EID: 0032514987     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980416j     Document Type: Article

References (25)

1. 2
2. Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenesis; Cambridge University Press: Cambridge, England, 1991.
3. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66. Harvey, R. G. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series Monograph 283; American Chemical Society: Washington, DC, 1985. Dipple, A.; Moschel, R. C.; Bigger, C. A. H. In Chemical Carcinogens, 2nd ed., Searle, C. E., Ed.; ACS Monograph No. 182; American Chemical Society: Washington, DC, 1984; pp 63-84. Conney, A. H. Cancer Res. 1982, 42, 4875 .
4. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66. Harvey, R. G. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series Monograph 283; American Chemical Society: Washington, DC, 1985. Dipple, A.; Moschel, R. C.; Bigger, C. A. H. In Chemical Carcinogens, 2nd ed., Searle, C. E., Ed.; ACS Monograph No. 182; American Chemical Society: Washington, DC, 1984; pp 63-84. Conney, A. H. Cancer Res. 1982, 42, 4875 .
5. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66. Harvey, R. G. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series Monograph 283; American Chemical Society: Washington, DC, 1985. Dipple, A.; Moschel, R. C.; Bigger, C. A. H. In Chemical Carcinogens, 2nd ed., Searle, C. E., Ed.; ACS Monograph No. 182; American Chemical Society: Washington, DC, 1984; pp 63-84. Conney, A. H. Cancer Res. 1982, 42, 4875 .
6. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66. Harvey, R. G. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series Monograph 283; American Chemical Society: Washington, DC, 1985. Dipple, A.; Moschel, R. C.; Bigger, C. A. H. In Chemical Carcinogens, 2nd ed., Searle, C. E., Ed.; ACS Monograph No. 182; American Chemical Society: Washington, DC, 1984; pp 63-84. Conney, A. H. Cancer Res. 1982, 42, 4875 .
7. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66. Harvey, R. G. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series Monograph 283; American Chemical Society: Washington, DC, 1985. Dipple, A.; Moschel, R. C.; Bigger, C. A. H. In Chemical Carcinogens, 2nd ed., Searle, C. E., Ed.; ACS Monograph No. 182; American Chemical Society: Washington, DC, 1984; pp 63-84. Conney, A. H. Cancer Res. 1982, 42, 4875 .
8. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66. Harvey, R. G. Polycyclic Hydrocarbons and Carcinogenesis; ACS Symposium Series Monograph 283; American Chemical Society: Washington, DC, 1985. Dipple, A.; Moschel, R. C.; Bigger, C. A. H. In Chemical Carcinogens, 2nd ed., Searle, C. E., Ed.; ACS Monograph No. 182; American Chemical Society: Washington, DC, 1984; pp 63-84. Conney, A. H. Cancer Res. 1982, 42, 4875 .
9. Nair, R. V.; Nettikumara, A. N.; Cortez, C.; Harvey, R. G.; DiGiovanni, J. Chem. Res. Toxicol. 1992, 5, 53 2.
10. Harvey, R. G.; Dai, W.; Zhang, J.-T.; Cortez, C. J. Org. Chem. 1998, 63, 8118.
11. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768 and references cited therein.
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13. (b) Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919.
14. (c) Bringmann, G.; Keller, P. A.; Rölfing, K. Synlett 1994, 423.
15. Tang, X.-Q.; Harvey, R. G. Tetrahedron Lett. 1995, 36, 6037.
16. Epoxybutane serves to prevent competing reactions by scavenging the HI produced: Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769.
17. Ashby, E. C.; Lin, J. J. J. Org. Chem. 1978, 43, 1263.
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19. Dai, W.; Abu-Shqara, E.; Harvey, R. G. J. Org. Chem. 1995, 60, 4905. Platt, K.; Oesch, F. Synthesis 1982, 459.
20. Reference 2, chapter 13, pp 306-329.
21. 2 serves to oxidize hydroquinones to quinones which undergo reduction with the hydride reagent to dihydrodiols plus variable amounts of hydroquinones which are then recycled.
22. Harvey, R. G.; Goh, S. H.; Cortez, C. J. Am. Chem. Soc. 1975, 97, 3468.
23. Mallory, F. B.; Mallory, C. W. Org. React. 1984, 30, 1.
24. Harvey, R. G. Polycyclic Aromatic Hydrocarbons; Wiley-VCH: New York, 1997.
25. Bedard, T. C.; Corey, J. Y.; Lange, L. D.; Rah, N. P. J. Organomet. Chem. 1991, 401, 261.