Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4985-4988

  Stover, James S ^a   Rizzo, Carmelo J ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 METHYLIMIDAZO[4,5 F]QUINOLINE; DEOXYGUANOSINE KINASE; DNA; MUTAGENIC AGENT; PALLADIUM; 2 AMINO 3 METHYLIMIDAZO(4,5 F)QUINOLINE; 2-AMINO-3-METHYLIMIDAZO(4,5-F)QUINOLINE; DEOXYGUANOSINE; QUINOLINE DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; SYNTHESIS; ALKYLATION; CHEMICAL STRUCTURE; CHEMISTRY;

ALKYLATION; CATALYSIS; DEOXYGUANOSINE; MOLECULAR STRUCTURE; PALLADIUM; QUINOLINES;

EID: 12344286968     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047851m     Document Type: Article

References (35)

1. This manuscript is dedicated to Professor Amos B. Smith, III, in celebration of his 60th birthday.
2. Heflich, R. H.; Neft, R. E. Mutat. Res. 1994, 318, 73-174.
3. Gonçalves, L. L.; Beland, F. A.; Marques, M. M. Chem. Res. Toxicol. 2001, 14, 165-174.
4. Yu, M. C.; Skipper, P. L.; Tannenbaum, S. R.; Chan, K. K.; Ross, R. K. Mutat. Res. 2002, 506-507, 21-28.
5. Turesky, R. J.; Freeman, J. P.; Holland, R. D.; Nestorick, D. M.; Miller, D. W.; Ratnasinghe, R. D.; Kadlubar, F. F. Chem. Res. Toxicol. 2003, 16, 1162-1173.
6. Turesky, R. J. Drug Metab. Rev. 2002, 34, 625-650.
7. Sugimura, T. Mutat. Res. 1997, 376, 211-219.
8. Guengerich, F. P. Drug Metab. Rev. 2002, 34, 607-623.
9. Novak, M.; Rajagopal, S.; Xu, L. L.; Kazerani, S.; Toth, K.; Brooks, M.; Nguyen, T. M. J. Phys. Org. Chem. 2004, 17, 615-624.
10. Turesky, R. J.; Markovic, J. Chem. Res. Toxicol. 1994, 7, 752-761.
11. Turesky, R. J.; Rossi, S. C.; Welti, D. H.; Lay, J. O.; Kadlubar, F. F. Chem. Res. Toxicol. 1992, 5, 479-490.
12. Turesky, R. J.; Box, R. M.; Markovic, J.; Gremaud, E.; Snyderwine, E. G. Mutat. Res. 1997, 376, 235-241.
13. Lakshman, M. K. J. Organomet. Chem. 2002, 653, 234-251.
14. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
15. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
16. Chida, N.; Suzuki, T.; Tanaka, S.; Yamada, I. Tetrahedron Lett. 1999, 40, 2573-2576.
17. Suzuki, T.; Suzuki, S. T.; Yamada, I.; Koashi, Y.; Yamada, K.; Chida, N. J. Org. Chem. 2002, 67, 2874-2880.
18. Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
19. De Riccardis, F.; Bonala, R. R.; Johnson, F. J. Am. Chem. Soc. 1999, 121, 10453-10460.
20. Harwood, E. A.; Sigurdsson, S. T.; Edfeldt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081-5082.
21. Harwood, E. A.; Hopkins, P. B.; Sigurdsson, S. T. J. Org. Chem. 2000, 65, 2959-2964.
22. De Riccardis, F.; Johnson, F. Org. Lett. 2000, 2, 293-295.
23. Bonala, R. R.; Shishkina, I. G.; Johnson, F. Tetrahedron Lett. 2000, 41, 7281-7284.
24. Lakshman, M. K.; Gunda, P. Org. Lett. 2003, 5, 39-42.
25. Johnson, F.; Bonala, R.; Tawde, D.; Torres, M. C.; Iden, C. R. Chem. Res. Toxicol. 2002, 15, 1489-1494.
26. Chakraborti, D.; Colis, L.; Schneider, R.; Basu, A. K. Org. Lett. 2003, 5, 2861-2864.
27. Lakshman, M. K.; Ngassa, F. N.; Bae, S.; Buchanan, D. G.; Hahn, H.-G.; Mah, H. J. Org. Chem. 2003, 68, 6020-6030.
28. Wang, Z.; Rizzo, C. J. Org. Lett. 2001, 3, 565-568.
29. Meier, C.; Gräsl, S. Synlett 2002, 802-804.
30. Gillet, L. C. J.; Schärer, O. D. Org. Lett. 2002, 4, 4205-4208.
31. Schoffers, E.; Olsen, P. D.; Means, J. C. Org. Lett. 2001, 3, 4221-4223.
32. Takamura-Enya, T.; Ishikawa, S.; Mochizuki, M.; Wakabayashi, K. Tetrahedron Lett. 2003, 44, 5969-5973.
33. Elmquist, C. E.; Stover, J. S.; Wang, Z.; Rizzo, C. J. J. Am. Chem. Soc. 2004, 126, 11189-11201.
34. Waterhouse, A. L.; Rapoport, H. J. Label. Compds. Radiopharm. 1985, 22, 201-216.
35. Brooks, M. E., Ph.D. Dissertation, Miami University, Oxford, OH, 2002.