Efficient syntheses of the active metabolites of carcinogenic polycyclic aromatic hydrocarbons

ACS Symposium Series

Volumn 865, Issue , 2003, Pages 115-126

  Harvey, Ronald G ^a   Dai, Qing ^a   Ran, Chongzhao ^a   Penning, Trevor M ^b  

^a UNIVERSITY OF CHICAGO   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 81855181677     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-2003-0865.ch008     Document Type: Article

References (45)

1. International Agency for Research on Cancer. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Polynuclear Aromatic Compounds, Part I, Chemical, Environmental and Experimental Data, Vol. 32, IARC, Lyon, France, 1983.
2. Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenesis, Cambridge University Press, Cambridge, U. K., 1991.
3. Harvey, R. G., Polycyclic Hydrocarbons and Carcinogenesis; American Chemical Society: Washington, DC, 1985.
4. Harvey, R. G. The Handbook of Environmental Chemistry, Volume 3, Part I: PAHs and Related Compounds, O. Hutzinger, Editor-in-Chief, A. Neilson, Volume Ed., Chap. 1, Springer, Berlin, Heidelberg, 1997, pp 1-54.
5. Dipple, A. DNA Adducts: Identification and Biological Significance, Hemminki, K.; Dipple, A.; Segerbäck, D.; Kadulbar, F. F.; Shuker, D.; Bartsch, H., Eds., IARC Scientific Publication No. 125, 1994, pp. 107-129.
6. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66-73.
7. Cavalieri, E. L.; Rogan, E. G. Xenobiotica, 1995, 25, 677-688.
8. Smithgall, T. E.; Harvey, R. G.; Penning, T. M. J. Biol. Chem. 1986, 261, 6184-6191.
9. Smithgall, T. E.; Harvey, R. G.; Penning, T. M. Cancer Res. 1988, 48, 1227-1232.
10. Smithgall, T. E.; Harvey, R. G.; Penning, T. M. J. Biol. Chem. 1988, 263, 1814-1820.
11. Penning, T. M.; Ohnishi, S. T.; Ohnishi, T., Harvey, R. G. Chem. Res. Toxicol. 1996, 9, 84-92.
12. Shou, M; Harvey, R. G.; Penning, T. M. Carcinogenesis 1993, 14, 475.
13. McCoull, K. D.; Rindgen, D.; Blair, I. A.; Penning, T. M. Chem. Res. Toxicol. 1999, 12, 237-246.
14. Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenesis, Cambridge University Press, Cambridge, U. K., 1991, Chap. 14, pp 330-359.
15. Beland, F. A; Harvey, R. G. J. Chem. Soc. Chem. Commun. 1976, 84-85.
16. Yagi, H.; Thakker, D. R.; Hernandez, O.; Koreeda, M.; Jerina, D. M. J. Am. Chem. Soc. 99, 1977, 1604-1611.
17. Harvey, R. G.; Sukumaran, K. Tetrahedron Lett. 1977, 28, 2387-2390.
18. Lee, H.; Harvey, R. G.; Cortez, C; Kiselyov, A. Bioorg. Med. Chem. Lett. 1997, 7, 443-446.
19. Lee, H.; Harvey, R. G. J. Org. Chem. 1986, 51, 3502-3507.
20. Lee, H.; Hinz, M.; Stezowski, J. J.; Harvey, R. G. Tetrahedron Lett. 1990, 31, 6773-6776.
21. Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613.
22. Laksman, M. K.; Sayer, J. M.; Jerina, D. M. J. Am. Chem. Soc. 1991, 113, 6589-6594.
23. Laksman, M. K.; Sayer, J. M.; Jerina, D. M. J. Org. Chem. 1992, 57, 3438-3443.
24. Cooper, M. D.; Hodge, R. P.; Tamura, P. J.; Wilkinson, A. S.; Harris, C. M.; Harris, T. M. Tetrahedron Lett. 2000, 41, 3555-3558.
25. Cosman, M.; Ibanez, V.; Geacintov, N. E.; Harvey, R. G. Carcinogenesis 1990, 11, 1667-1672.
26. F.-J. Zhang, F.-J.; Cortez, C; Harvey, R. G. J. Org. Chem. 2000, 65, 3952.
27. Mataka, S.; Liu, G. B.; Sawada, T.; Kurisa, M.; Tashiro, M. Bull Chem. Soc. Japan 1994, 67, 1113-1119.
28. Makasza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094-5100.
29. Mataka, S.; Liu, G.-B.; Sawada, T.; Tori-I, A.; Tashiro, M., J. Chem. Res. (S) 1995, 410-411.
30. Nicolaou, K. C; Momtagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245-2258.
31. Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R. Org. Lett. 2001, 4, 285-288.
32. Cho, H.; Harvey, R. G. J. C. S Perkin I. 1976, 836-839.
33. Harvey, R. G.; Fu, P. P. In, Polycyclic Hydrocarbons and Cancer: Environment, Chemistry, and Metabolism. Vol. 1. Gelboin, H. V.; T'so, P. O. P., Eds., Academic Press, New York, 1978, pp. 133-165.
34. Platt, K. L.; Oesch, F. J. Org. Chem. 1983, 48, 265-268.
35. Sharma, P. K. Syn. Commun. 1993, 23, 389-394.
36. Washburn, R. M; Levens, E.; Albright, C. F.; Billig, F. A. Org. Syn., Coll. Vol. 4, 1963, p. 68-72.
37. Harmata, M.; Kahraman, M. J. Org. Chem. 1999, 64, 4949-4952.
38. Leo, P.-M.; Morin, C; Philouze, C. Org. Lett. 2002, 4, 2711-2714.
39. Kumar, S. J. Chem. Soc. Perkin Trans. 1 1998, 3157-3161.
40. Sukumaran, K. B.; Harvey, R. G. J. Org. Chem. 1980, 45, 4407-4413.
41. Newman, M. S.; Khanna, J. M.; Khanna, V. K.; Kanakarajan, K. J. Org. Chem. 1979, 44, 4994-4995.
42. Konieczny, M.; Harvey, R. G. J. Org. Chem. 1979, 44, 4813-4816.
43. Reference 2, p. 369.
44. Mallory, F. B.; Mallory, C. W. Org. Reactions, 1984, 30, 1-456.
45. Harvey, R. G.; Cortez, C; Sugiyama, T.; Ito, Y.; Sawyer, T. W.; DiGiovanni, J. J. Medic. Chem. 1988, 31, 154-159.