Synthesis of pyrene and benzo[a]pyrene adducts at the exocyclic amino groups of 2′-deoxyadenosine and 2′-deoxyguanosine by a palladium-mediated C - N bond-formation strategy

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 6020-6030

  Lakshman, Mahesh K ^a   Ngassa, Felix N ^b   Bae, Suyeal ^c   Buchanan, Dennis G ^a   Hahn, Hoh Gyu ^d   Mah, Heduck ^c  

^a CITY COLLEGE OF NEW YORK   (United States)

^b UNIVERSITY OF NORTH DAKOTA   (United States)

^c Kyonggi University   (South Korea)

^d Korea Institute of Science and Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHEMICAL ACTIVATION; CHEMICAL BONDS; CONFORMATIONS; DERIVATIVES; NITROGEN; OXIDATION; PALLADIUM; SYNTHESIS (CHEMICAL);

BOND FORMATION;

HYDROCARBONS;

AROMATIC AMINE; AROMATIC HYDROCARBON; BENZO[A]PYRENE DERIVATIVE; BROMIDE; CARBON; CARCINOGEN; CATION; DEOXYADENOSINE; DEOXYGUANOSINE; DIMER; DNA BASE; HALIDE; HALONUCLEOSIDE; HYDROCARBON; N2 (1 PYRENYL) 2' DEOXYGUANOSINE; N2 (6 BENZO[A]PYRENYL) 2' DEOXYGUANOSINE; N6 (1 PYRENYL) 2' DOXYADENOSINE; N6 (6 BENZO[A]PYRENYL) 2' DEOXYADENOSINE; NITROGEN; NUCLEOSIDE DERIVATIVE; PALLADIUM; PURINE; PYRENE; RADICAL; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL BOND; DIMERIZATION; DNA ADDUCT; DNA ALKYLATION; DNA CONFORMATION; METABOLIC ACTIVATION; OXIDATION; REACTION ANALYSIS; SINGLE ELECTRON OXIDATION; SYNTHESIS;

AMINES; BENZO(A)PYRENE; CATALYSIS; DEOXYGUANOSINE; DNA ADDUCTS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PALLADIUM; PYRENES;

EID: 0037696809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030113b     Document Type: Article

References (70)

1. PAH carcinogenesis has been reviewed in: (a) Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships; Yang, S. K., Silverman, B. D., Eds.; CRC Press: Boca Raton, FL, 1988; Vols. I and II. (b) Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Harvey, R. G., Ed.; Cambridge University Press: Cambridge, UK, 1991. (c) Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; ACS Symp. Ser. 283: Washington, DC, 1985.
2. PAH carcinogenesis has been reviewed in: (a) Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships; Yang, S. K., Silverman, B. D., Eds.; CRC Press: Boca Raton, FL, 1988; Vols. I and II. (b) Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Harvey, R. G., Ed.; Cambridge University Press: Cambridge, UK, 1991. (c) Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; ACS Symp. Ser. 283: Washington, DC, 1985.
3. PAH carcinogenesis has been reviewed in: (a) Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships; Yang, S. K., Silverman, B. D., Eds.; CRC Press: Boca Raton, FL, 1988; Vols. I and II. (b) Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity; Harvey, R. G., Ed.; Cambridge University Press: Cambridge, UK, 1991. (c) Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; ACS Symp. Ser. 283: Washington, DC, 1985.
4. Reviewed in: (a) Thakker, D. R.; Levin, W.; Wood, A. W.; Conney, A. H.; Yagi, H.; Jerina, D. M. In Drug Stereochemistry, Analytical Methods and Pharmacology; Wainer, I. W., Drayer, D. E., Eds.; Marcel Dekker: New York, 1988; pp 271-296.
5. (b) Jerina, D. M.; Sayer, J. M.; Agarwal, S. K.; Yagi, H.; Levin, W.; Wood, A. W.; Conney, A. H.; Pruess-Schwartz, D.; Baird, W. M.; Pigott, M. A.; Dipple, A. In Biological Reactive Intermediates III; Kocsis, J. J., Jollow, D. J., Witmer, C. M., Nelson, J. O., Snyder, R., Eds.; Plenum Press: New York, 1986; pp 11-30.
6. (c) Jerina, D. M.; Sayer, J. M.; Yagi, H.; Croisy-Delcey, M.; Ittah, Y.; Thakker, D. R.; Wood, A. W.; Chang, R. L.; Levin, W.; Conney, A. H. In Biological Reactive Intermediates II, Part A; Snyder, R., Parke, D. V., Kocsis, J. J., Jollow, D. J., Gibson, C. G., Witmer, C. M., Eds.; Plenum Press: New York, 1986; pp 501-523.
7. (a) Dipple, A. In DNA Adducts: Identification and Biological Significance; Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Sagerbäck, D., Bartsch, H., Eds.; Scientific Publication No. 125; International Agency for Research on Cancer: Lyon, 1994; pp 107-129.
8. (b) Szeliga, J.; Dipple, A. Chem. Res. Toxicol. 1998, 11, 1-11.
9. (c) Jerina, D. M.; Chadha, A.; Cheh, A. M.; Schurdak, M. E.; Wood, A. W.; Sayer, J. M. In Biological Reactive Intermediates IV; Witmer, C. M., Snyder, R., Jollow, D. J., Kalf, G. F., Kocsis, J. J., Sipes, I. G., Eds.; Plenum Press: New York, 1991; pp 533-553.
10. (a) Cavalieri, E.; Rogan, E. In Polycyclic Aromatic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; ACS Symp. Ser. No. 283: Washington, DC, 1985; pp 290-305.
11. (b) Cavalieri, E.; Rogan. E. Environ. Health Perspect. 1985, 64, 69-84.
12. Chen, L.; Devanesan, P. D.; Higginbotham, S.; Ariese, F.; Jankowiak, R.; Small, G. J.; Rogan, E. G.; Cavalieri, E. L. Chem. Res. Toxicol. 1996, 9, 897-903.
13. Rogan, E. G.; RamaKrishna, N. V. S.; Higginbotham, S.; Cavalieri, E. L.; Jeong, H.; Jankowiak, R.; Small, G. J. Chem. Res. Toxicol. 1990, 3, 441-444.
14. Rogan, E. G.; Devanesan, P. D.; RamaKrishna, N. V. S.; Higginbotham, S.; Padmavathi, N. S.; Chapman, K.; Cavalieri, E. L.; Jeong, H.; Jankowiak, R.; Small, G. J. Chem. Res. Toxicol. 1993, 6, 356-363.
15. Todorovic, R.; Ariese, F.; Devanesan, P.; Jankowiak, R.; Small, G. J.; Rogan, E.; Cavalieri, E. Chem. Res. Toxicol. 1997, 10, 941-947.
16. Devanesan, P. D.; RamaKrishna, N. V. S.; Todorovic, R.; Rogan, E. G.; Cavalieri, E. L.; Jeong, H.; Jankowiak, R.; Small, G. J. Chem. Res. Toxicol. 1992, 5, 302-309.
17. Rogan, E. G.; Cavalieri, E. L.; Tibbels, S. R.; Cremonesi, P.; Warner, C. D.; Nagel, D. L.; Tomer, K. B.; Cerny, R. L.; Gross, M. L. J. Am. Chem. Soc. 1988, 110, 4023-4029.
18. (a) Rochlitz, J. Tetrahedron 1967, 23, 3043-3048.
19. (b) Jeftic, L.; Adams, R. N. J. Am. Chem. Soc. 1970, 92, 1332-1337.
20. (c) Johnson, M. D.; Calvin, M. Nature 1973, 241, 271-272.
21. Chakravarti, D.; Pelling, J. C.; Cavalieri, E. L.; Rogan, E. G. Proc. Natl. Acad. Sci. 1995, 92, 10422-10426.
22. For some examples on the site-specific modification of DNA by diol epoxides, please see: (a) Lakshman, M. K.; Chaturvedi, S. Carcinogenesis 1996, 17, 2747-2752. (b) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481. (c) Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774. (d) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613. (e) Mao, B.; Xu, J.; Li, B.; Margulis, L. A.; Smirnov, S.; Ya, N. Q.; Coutney, S.; Geacintov, N. E. Carcinogenesis 1995, 16, 357-365. (f) DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris. T. M. Chem. Res. Toxicol. 1996, 9, 630-637. (g) Kroth, H.; Yagi, H.; Seidel, A.; Jerina, D. M. J. Org. Chem. 2000, 65, 5558-5564.
23. For some examples on the site-specific modification of DNA by diol epoxides, please see: (a) Lakshman, M. K.; Chaturvedi, S. Carcinogenesis 1996, 17, 2747-2752. (b) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481. (c) Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774. (d) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613. (e) Mao, B.; Xu, J.; Li, B.; Margulis, L. A.; Smirnov, S.; Ya, N. Q.; Coutney, S.; Geacintov, N. E. Carcinogenesis 1995, 16, 357-365. (f) DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris. T. M. Chem. Res. Toxicol. 1996, 9, 630-637. (g) Kroth, H.; Yagi, H.; Seidel, A.; Jerina, D. M. J. Org. Chem. 2000, 65, 5558-5564.
24. For some examples on the site-specific modification of DNA by diol epoxides, please see: (a) Lakshman, M. K.; Chaturvedi, S. Carcinogenesis 1996, 17, 2747-2752. (b) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481. (c) Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774. (d) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613. (e) Mao, B.; Xu, J.; Li, B.; Margulis, L. A.; Smirnov, S.; Ya, N. Q.; Coutney, S.; Geacintov, N. E. Carcinogenesis 1995, 16, 357-365. (f) DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris. T. M. Chem. Res. Toxicol. 1996, 9, 630-637. (g) Kroth, H.; Yagi, H.; Seidel, A.; Jerina, D. M. J. Org. Chem. 2000, 65, 5558-5564.
25. For some examples on the site-specific modification of DNA by diol epoxides, please see: (a) Lakshman, M. K.; Chaturvedi, S. Carcinogenesis 1996, 17, 2747-2752. (b) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481. (c) Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774. (d) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613. (e) Mao, B.; Xu, J.; Li, B.; Margulis, L. A.; Smirnov, S.; Ya, N. Q.; Coutney, S.; Geacintov, N. E. Carcinogenesis 1995, 16, 357-365. (f) DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris. T. M. Chem. Res. Toxicol. 1996, 9, 630-637. (g) Kroth, H.; Yagi, H.; Seidel, A.; Jerina, D. M. J. Org. Chem. 2000, 65, 5558-5564.
26. For some examples on the site-specific modification of DNA by diol epoxides, please see: (a) Lakshman, M. K.; Chaturvedi, S. Carcinogenesis 1996, 17, 2747-2752. (b) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481. (c) Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774. (d) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613. (e) Mao, B.; Xu, J.; Li, B.; Margulis, L. A.; Smirnov, S.; Ya, N. Q.; Coutney, S.; Geacintov, N. E. Carcinogenesis 1995, 16, 357-365. (f) DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris. T. M. Chem. Res. Toxicol. 1996, 9, 630-637. (g) Kroth, H.; Yagi, H.; Seidel, A.; Jerina, D. M. J. Org. Chem. 2000, 65, 5558-5564.
27. For some examples on the site-specific modification of DNA by diol epoxides, please see: (a) Lakshman, M. K.; Chaturvedi, S. Carcinogenesis 1996, 17, 2747-2752. (b) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481. (c) Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774. (d) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613. (e) Mao, B.; Xu, J.; Li, B.; Margulis, L. A.; Smirnov, S.; Ya, N. Q.; Coutney, S.; Geacintov, N. E. Carcinogenesis 1995, 16, 357-365. (f) DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris. T. M. Chem. Res. Toxicol. 1996, 9, 630-637. (g) Kroth, H.; Yagi, H.; Seidel, A.; Jerina, D. M. J. Org. Chem. 2000, 65, 5558-5564.
28. For some examples on the site-specific modification of DNA by diol epoxides, please see: (a) Lakshman, M. K.; Chaturvedi, S. Carcinogenesis 1996, 17, 2747-2752. (b) Kim, S. J.; Stone, M. P.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1992, 114, 5480-5481. (c) Steinbrecher, T.; Becker, A.; Stezowski, J. J.; Oesch, F.; Seidel, A. Tetrahedron Lett. 1993, 34, 1773-1774. (d) Lee, H.; Luna, E.; Hinz, M.; Stezowski, J. J.; Kiselyov, A. S.; Harvey, R. G. J. Org. Chem. 1995, 60, 5604-5613. (e) Mao, B.; Xu, J.; Li, B.; Margulis, L. A.; Smirnov, S.; Ya, N. Q.; Coutney, S.; Geacintov, N. E. Carcinogenesis 1995, 16, 357-365. (f) DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris. T. M. Chem. Res. Toxicol. 1996, 9, 630-637. (g) Kroth, H.; Yagi, H.; Seidel, A.; Jerina, D. M. J. Org. Chem. 2000, 65, 5558-5564.
29. Hanson, A. A.; Rogan, E. G.; Cavalieri, E. L. Chem. Res. Toxicol. 1998, 11, 1201-1208.
30. (a) Ramakrishna, N. V. S.; Gao, F.; Padmavathi, N. S.; Cavalieri, E. L.; Rogan, E. G.; Cerny, R. L.; Gross, M. L. Chem. Res. Toxicol. 1992, 5, 293-302.
31. (b) Li, K.-M.; Byun, J.; Gross, M. L.; Zamzow, D.; Jankowiak, R.; Rogan, E. G.; Cavalieri, E. L. Chem. Res. Toxicol. 1999, 12, 749-757.
32. Reviewed in: (a) Hartwig, J. F. Synlett 1997, 329-340.
33. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
34. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1999, 31, 805-818.
35. (d) Hartwig, J. F. Acc. Chem. Res. 1999, 31, 852-860.
36. (e) Frost, C. G.; Mendonca, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615-2623.
37. (f) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
38. (g) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: New York, 2000; pp 195-262.
39. (h) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
40. (a) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
41. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
42. (c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
43. (d) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
44. (e) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370.
45. (f) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367-2370.
46. (g) Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
47. (h) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
48. (i) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729-7737.
49. Reviewed in: Lakshman, M. K. J. Organomet. Chem. 2002, 653, 234-251.
50. Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
51. Harwood, E. A.; Sigurdsson, S. T.; Edfeldt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081-5082.
52. Harwood, E. A.; Hopkins, P. B.; Sigurdsson, S. T. J. Org. Chem. 2000, 65, 2959-2964.
53. Bonala, R.; Shishkina, I. G.; Johnson, F. Tetrahedron Lett. 2000, 41, 7281-7284.
54. Wang, Z.; Rizzo, C. J. Org. Lett. 2001, 3, 565-568.
55. Schoffers, E.; Olsen, P. D.; Means, J. C. Org. Lett. 2001, 3, 4221-4223.
56. Meier, C.; Gräsl, S. Synlett 2002, 802-804.
57. De Riccardis, F.; Bonala, R. R.; Johnson, F. J. Am. Chem. Soc. 1999, 121, 10453-10460.
58. 1-Bromopyrene and 1-aminopyrene are commercially available from one or more sources.
59. Dewhurst, F.; Kitchen, D. A. J. Chem. Soc., Perkin Trans. 1 1972, 710-712.
60. Fieser, L. F.; Hershberg, E. B. J. Am. Chem. Soc. 1939, 61, 1565-1574.
61. 3 is the correct reagent.
62. Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngassa, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779-7787.
63. 2 in the presence of 2,6-lutidine at -30 to -35 °C.
64. De Riccardis, F.; Johnson, F. Org. Lett. 2000, 3, 293-295.
65. Véliz, E. A.; Beal, P. A. J. Org. Chem. 2001, 66, 8592-8598.
66. Lakshman, M. K.; Lehr, R. E. Nucleosides Nucleotides 1992, 11, 1039-1046.
67. (a) Lakshman, M. K.; Sayer, J. M.; Jerina, D. M. J. Am. Chem. Soc. 1991, 113, 6589-6594.
68. (b) Lakshman, M. K.; Sayer, J. M.; Jerina, D. M. J. Org. Chem. 1992, 57, 3438-3443.
69. (c) Lakshman, M. K.; Sayer, J. M.; Yagi, H.; Jerina, D. M. J. Org. Chem. 1992, 57, 4585-4590.
70. Lakshman, M. K.; Gunda, P. Org. Lett. 2003, 5, 39-42.