Efficient N-arylation and N-alkenylation of the five DNA/RNA nucleobases

Journal of Organic Chemistry

Volumn 71, Issue 24, 2006, Pages 9183-9190

  Jacobsen, Mikkel F ^a   Knudsen, Martin M ^a   Gothelf, Kurt V ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CONDENSATION; NITROGEN; SUBSTITUTION REACTIONS;

MASKED NUCLEOBASES; N-ALKENYLATION; N-ARYLATION;

DNA;

ADENINE DERIVATIVE; ALKENYL GROUP; BORONIC ACID DERIVATIVE; COPPER; CYTOSINE DERIVATIVE; DNA; GUANINE DERIVATIVE; NUCLEIC ACID BASE; PYRIMIDINE DERIVATIVE; RNA; THYMINE DERIVATIVE; URACIL DERIVATIVE;

ARTICLE; ARYLATION; BASE PAIRING; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

DNA; MAGNETIC RESONANCE SPECTROSCOPY; RNA; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 33751575313     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061694i     Document Type: Article

References (79)

1. For some recent reviews, see: (a) Kimura, K.-I.; Bugg, T. D. H. Nat. Prod. Rep. 2003, 20, 252-273.
2. (b) Simons, C.; Wu, Q.; Htar, T. T. Curr. Top. Med. Chem. 2005, 5, 1191-1203.
3. Kool, E. T. Chem. Rev. 1997, 97, 1473-1487.
4. Neidle, S. Nucleic Acid Structure and Recognition; Oxford University Press: Oxford, 2002.
5. (a) Otero, R.; Schöck, M.; Molina, L. M.; Lægsgaard, E.; Stensgaard, I.; Hammer, B.; Besenbacher, F. Angew. Chem., Int. Ed. 2005, 44, 2270-2275.
6. (b) Xu, S. L.; Dong, M.; Rauls, E.; Otero, R.; Linderoth, T. R.; Besenbacher, F. Nano Lett. 2006, 6, 1434-1438.
7. (a) Ueno, Y.; Kato, T.; Sato, K.; Ito, Y.; Yoshida, M.; Inoue, T.; Shibata, A.; Ebihara, M.; Kitade, Y. J. Org. Chem. 2005, 70, 7925-7935.
8. (b) Sauter, G.; Stulz, E.; Leumann, C. Helv. Chim. Acta 1998, 81, 14-34.
9. (c) Sauter, G.; Leumann, C. Helv. Chim. Acta 1998, 81, 916-931.
10. N-Arylpurines: (a) Harada, H.; Asano, O.; Kawara, T.; Inoue, T.; Horizoe, T.; Yasuda, N.; Nagata, K.; Murakami, M.; Nagaoka, J.; Kobayashi, S.; Tanaka, I.; Abe, S. Bioorg. Med. Chem. 2001, 9, 2709-2726.
11. (b) Kumagai, T.; Okubo, T.; Kataoka-Okubo, H.; Chaki, S.; Okuyama, S.; Nakazato, A. Bioorg. Med. Chem. 2001, 9, 1357-1363.
12. (c) Moriguchi, I.; Kanada, Y. Chem. Pharm. Bull. 1977, 25, 926-935.
13. (d) Young, R. C.; Jones, M.; Milliner, K. J.; Rana, K. K.; Ward, J. G. J. Med. Chem. 1990, 33, 2073-2080.
14. (e) Brakta, M.; Murthy, D.; Ellis, L.; Phadtare, S. Bioorg Med. Chem. Lett. 2002, 12, 1489-1492.
15. (f) Baker, B. R.; Siebeneick, H. U. J. Med. Chem. 1971, 14, 802-805.
16. (g) Bakkestuen, A. K.; Gundersen, L.-L.; Langli, G.; Liu, F.; Nolsøe, J. M. J. Bioorg. Med. Chem. Lett. 2000, 10, 1207-1210.
17. (h) Gundersen, L.-L.; Nissen-Meyer, J.; Spilsberg, B. J. Med. Chem. 2002, 45, 1383-1386.
18. (i) Koppel, H. C.; Robins, R. K. J. Am. Chem. Soc. 1958, 80, 2751-2755.
19. (j) Koppel, H. C.; O'Brien, D. E.; Robins, R. K. J. Am. Chem. Soc. 1959, 81, 3046-3051.
20. (k) Sen, D.; Dasgupta, A.; Sengupta, P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24B, 952-958.
21. (l) Basyouni, W. M.; Hosni, H. M.; Helmy, S. M. Egypt. J. Chem. 1999, 42, 587-598.
22. (m) El-Bayouki, K. A. M.; Haggag, B.; Basyouni, W. M. Egypt. J. Chem. 1990, 33, 243-253.
23. N-Arylpyrimidines: Brown, D. J. In Comprehensive Heterocyclic Chemistry - The Structure, Reaction, Synthesis and Uses of Heterocyclic Compounds; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 3, p 57.
24. (a) Gothelf, K. V.; LaBean, T. H. Org. Biomol. Chem. 2005, 3, 4023-4037.
25. (b) Gothelf, K. V.; Brown, R. S. Chem. Eur. J. 2005, 11, 1062-1069.
26. (c) Gothelf, K. V.; Thomsen, A.; Nielsen, M.; Cló, E.; Brown, R. S. J. Am. Chem. Soc. 2004, 26, 1044-1046.
27. (d) Nielsen, M; Thomsen, A. H.; Cló, E.; Kirpekar, F.; Gothelf, K. V. J. Org. Chem. 2004, 69, 2240.
28. (e) Brown, R. S.; Nielsen, M.; Gothelf, K. V. Chem. Commun. 2004, 13, 1464-1465.
29. (f) Nielsen, M.; Dauksaite, V.; Kjems, J.; Gothelf, K. V. Bioconjugate Chem. 2005, 16, 681-685.
30. (g) Blakskjær, P.; Gothelf, K. V. Org. Biomol. Chem. 2006, 4, 3442-3447.
31. Weigelt, S.; Busse, C.; Petersen, L.; Rauls, L.; Hammer, B.; Gothelf, K. V.; Besenbacher, F.; Linderoth, T. R. Nat. Mater. 2006, 5, 112-117.
32. N-Alkylpurines: (a) Kjellberg, J.; Johansson, N. G. Nucleosides Nucleotides 1989, 8, 225-256 and references therein.
33. (b) Novák, J.; Linhart, I.; Dvořáková, H. Eur. J. Org. Chem. 2004, 2738-2746.
34. (c) Kalayanov, G.; Jakša, S.; Scarcia, T.; Kobe, J. Synthesis 2004, 12, 2076-2034.
35. (d) Zhong, M.; Nowak, I.; Cannon, J. F.; Robins, M. J. J. Org. Chem. 2006, 71, 4216-4221 and references therein.
36. N-Alkylpyrimidines: (a) Ward, A. D.; Baker, B. R. J. Med. Chem. 1977, 20, 88-92.
37. (b) Ewing, D. F.; Glacon, V.; Len, C.; Mackenzie, G. New J. Chem. 2005, 29, 1461-1468.
38. (c) Zhang, L.; Peritz, A.; Meggers, E. J. Am. Chem. Soc. 2005, 127, 4174-4175.
39. (d) Wu, F.; Buhendwa, M. G.; Weaver, D. F. J. Org. Chem. 2004, 69, 9307-9309.
40. (e) Diederichsen, U.; Weicherding, D.; Diezemann, N. Org. Biomol. Chem. 2005, 6, 1058-1066.
41. Monographs and comprehensive reviews: (a) Lister, J. H. In The Chemistry of Heterocyclic Coumpounds; Weissberger, A., Taylor, E. C., Eds.; Wiley-Interscience: New York, 1971; Vol. 24.
42. (b) Shaw, G. In Comprehensive Heterocyclic Chemistry - The Structure, Reaction, Synthesis and Uses of Heterocyclic Compounds; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: New York, 1984; Vol. 5, pp 501-597.
43. (c) Ewing, D. F.; Mackenzie, G. In Second Supplements to the 2nd Edition of Rodd's Chemistry of Carbon Compounds; Sainsbury, M., Ed.; Elsevier Science B. V.: Amsterdam, 1999; Vol. IV K(partial)/L, pp 127-179.
44. Stig, A. J.; Synne, R.; Tore, B. J. Chem. Soc., Perkin Trans. 1 1999, 3265-3268.
45. Zhou, T.; Li, T.-C.; Chen, Z.-C. Helv. Chim. Acta 2005, 88, 290-296.
46. (a) Gondela, A.; Walczak, K. Tetrahedron: Asymmetry 2005, 16, 2107-2112.
47. (b) Boga, C.; Bonmartini, A. C.; Forlani, L.; Modarelli, V.; Righi, L.; Sgarabotto, P. J. Chem. Res., Miniprint 2001, 12, 1217-1231.
48. Boesen, T.; Madsen, C.; Henriksen, U.; Dahl, O. J. Chem. Soc., Perkin Trans. 1 2000, 2015-2021.
49. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
50. Some recent examples: (a) Chiang, G. C. H.; Olsson, T. Org. Lett. 2004, 6, 3079-3082.
51. (b) Sasaki, M.; Dalili, S.; Yudin, A. K. J. Org. Chem. 2003, 68, 2045-2047.
52. (c) Yu, S.; Saenz, J.; Srirangam, J. K. J. Org. Chem. 2002, 67, 1699-1702.
53. (d) Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077-2079.
54. (e) Lam, P. Y. S.; Vincent, G.; Clark, C. G.; Deudon, S.; Jadhav, P. K. Tetrahedron Lett. 2001, 42, 3415-3418.
55. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233-1236.
56. (g) Mederski, W. W. K. R.; Lefort, M.; Germann, M.; Kux, D. Tetrahedron 1999, 55, 12757-12770.
57. Ding, S.; Gray, S. N.; Ding, Q.; Schultz, P. G. Tetrahedron Lett. 2001, 42, 8751-8755.
58. Bakkestuen, A. K.; Gundersen, L.-L. Tetrahedron Lett. 2003, 44, 3359-3362.
59. Yue, Y.; Zheng, Z.-G.; Wu, B.; Xia, C.-Q.; Yu, X.-Q. Eur. J. Org. Chem. 2005, 5154-5157.
60. Jaime-Figueroa, S.; Zamilpa, A.; Guzman, A.; Morgans, D. J. Synth. Commun. 2001, 31, 3739-3746.
61. Frieden, M.; Giraud, M.; Reese, C. B.; Song, Q. J. Chem. Soc., Perkin Trans. 1 1998, 2827-2832.
62. Hosmane, R. S.; Leonard, N. J. J. Org. Chem. 1981, 46, 1457-1465.
63. Barrio, J. R.; Bryant, J. D.; Keyser, G. E. J. Med. Chem. 1980, 23, 572-574.
64. Mizutani, M.; Sanemitsu, Y.; Tamaru, Y.; Yoshida, Z.-I. Tetrahedron 1985, 41, 5289-5294.
65. 1-alkenylation had taken place.
66. Dey, S.; Garner, P. J. Org. Chem. 2000, 65, 7697-7699.
67. See Supporting Information.
68. For some examples, see: (a) Garcia-Teran, J. P.; Castillo, O.; Luque, A.; Garcia-Couceiro, U.; Roman, P.; Lloret, F. Inorg. Chem. 2004, 43, 5761-5770.
69. (b) Song, B.; Zhao, J.; Griesser, R.; Meiser, C.; Sigel, H.; Lippert, B. Chem. Eur. J. 1999, 5, 2374-2387.
70. (c) Steinkopf, S.; Liu, Q.; Froeystein, N. A.; Sletten, E. Acta Chem. Scand. 1992, 46, 446-450.
71. (d) Jitsukawa, K.; Mizutani, M.; Arii, H.; Kubo, I.; Izu, Y.; Ozawa, T.; Masuda, H. Chem. Lett. 2004, 33, 1302-1303.
72. (a) Kjellberg, J.; Hagberg, C.-E.; Malm, A.; Noren, J. O.; Johansson, N. G. Acta Chem. Scand. 1986, B40, 310-312.
73. (b) Kobe, J.; Kjellberg, J.; Johansson, N. G. Acta Chem. Scand. 1987, B41, 564-568.
74. (a) Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 114, 10056-10058.
75. (b) Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. J. Am. Chem. Soc. 1997, 119, 311-325.
76. Baker, B. R.; Wood, W. F. J. Med. Chem. 1967, 10, 1101-1105.
77. Baker, B. R.; Santi, D. V. J. Med. Chem. 1967, 10, 62-64.
78. Baker, B. R.; Kozma, J. J. Med. Chem. 1967, 10, 682-685.
79. Young, R. C.; Jones, M.; Milliner, K. J.; Rana, K. K.; Ward, J. G. J. Med. Chem. 1990, 33, 2073-2080.