Synthesis of potentially photoactivatable coumarin derivatives via a 1,3-dipolar cycloaddition

Journal of Heterocyclic Chemistry

Volumn 45, Issue 5, 2008, Pages 1429-1435

  Chenot, Elodie Denise ^a   Rodríguez Domínguez, Juan Carlos ^a   Hannewald, Paul ^a   Comel, Alain ^a   Kirsch, Gilbert ^a  

^a UNIVERSITÉ DE LORRAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; COPPER; COUMARIN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PHOTOACTIVATION; SYNTHESIS;

EID: 51849154289     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450528     Document Type: Article

References (70)

1. (a) Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry Pawda, A. Ed.; Wiley, New York, 1984; Vol 1, pp 1-176.
2. (b) Huisgen, R. Angew. Chem. Int. Ed. 1963, 2, 565.
3. (c) Huisgen, R. Angew. Chem. Int. Ed. 1963, 2, 633.
4. Kolb, H. C.; Finn, M. G.; Sharples, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
5. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
6. Agard, N. J.; Prescher, J. A.; Bertozzi, C. R. J. Am. Chem. Soc. 2004, 126, 15046.
7. Arosio, D.; Bertoli, M.; Manzonib, L.; Scolasticoa, C. Tetrahedron Lett. 2006, 47, 3697.
8. Kosiova, I.; Kovackova, S.; Kois, P. Tetrahedron 2007, 63, 312.
9. Natala, S. R., Muralidhar, R. M., Stephen, C.; Kiranmai G.; Stanley C. B.; Premkumar, R.; Ramana, M. V. R. Bioorg. Med. Chem. Lett. 2004, 14, 4093.
10. (a) Yang, Z.-Y.; Xia, Y.; Xia, P.; Cosentino, L. M.; Lee, K.-H. Bioorg. Med. Chem. Lett. 1998, 8, 1483.
11. (b) Spino, C.; Dodier, M.; Sotheeswaran, S. Bioorg. Med. Chem. Lett. 1998, 8, 3475.
12. (c) Bedoya, L. M.; Beltrán, M.; Sancho, R.; Olmedo, D. A.; Sánchez-Palomino, S.; del Olmo, E.; López-Pérez, J. L.; Muñoz, E.; San Feliciano, A.; Alcamí, J. Bioorg. Med. Chem. Lett. 2005, 15, 4447.
13. (a) Khan, I. A.; Kulkarni, M. V.; Sun, C.-M. Eur. J. Med. Chem. 2005, 40, 1168.
14. (b) Bonsignore, L.; Cottiglia, F.; Elkhaili, H.; Jehl, F.; Lavagna, S. M.; Loy, G.; Manna, F.; Monteil, H.; Pompei, D.; Secci, D. Il Farmaco 1998, 53, 425.
15. (a) Manolov, I.; Danchev, N. Eur. J. Med. Chem. 1995, 30, 531.
16. (b) Manolov, I.; Maichle-Moessmer, C.; Danchev, N. Eur. J. Med. Chem. 2006, 41, 882.
17. Bariana, D. S. J. Med. Chem. 1970, 13, 544.
18. (a) Ghate, M.; Kusanur, R. A.; Kulkarni, M. V. Eur. J. Med. Chem. 2005, 40, 882.
19. (b) Ghate, M.; Manohar, D.; Kulkarni, V.; Shobha, R.; Kattimani, S. Y. Eur. J. Med. Chem. 2003, 38, 297.
20. (c) Kontogiorgis, C. A.; Hadjipavlou-Litina, D. J. J. Med. Chem. 2005, 48, 6400.
21. (a) Beillerot, A.; Rodríguez Domínguez, J. C.; Kirsch, G.; Bagrel, D. Bioorg. Med. Chem. Lett. 2008, in press,
22. (b) Tyagi, Y. K.; Kumar, A.; Raj, H. G.; Vohra, P.; Gupta, G.; Kumari, R.; Kumar, P.; Gupta, R. K. Eur. J. Med. Chem. 2005, 40, 413.
23. (a) Peng, F.-C.; Cheng, J.-S. Mycopathologia 1997, 137, 125.
24. (b) Garino, C.; Pietrancosta, N.; Laras, Y.; Moret, V.; Rolland, A.; Quéléver, G.; Kraus, J.-L. Bioorg. Med. Chem. Lett. 2006, 16, 1995.
25. (c) Cravotto, G.; Balliano, G.; Robaldo, B.; Oliaro-Bosso, S.; Chimichib, S.; Boccalini, M. Bioorg. Med. Chem. Lett. 2004, 14, 1931.
26. (d) Onderwater, R. C. A.; Venhorst, J.; Commandeur, J. N. M.; Vermeulen, N. P. E. Chem. Res. Toxicol. 1999, 12, 555.
27. (e) Laurin, P.; Ferroud, D.; Klich, M.; Dupuis-Hamelin, C.; Mauvais, P.; Lassaigne, P.; Bonnefoy, A.; Musicki, B. Bioorg. Med. Chem. Lett. 1999, 9, 2079.
28. Seela, F.; Sirivolu, V. R.; Chittepu, P. Bioconjugate Chem. 2008, 19, 211.
29. (a) Kosiova, I.; Kovackova, S.; Kois, P. Tetrahedron 2007, 63, 312.
30. (b) Nonaka, H.; Tsukiji, S.; Ojida, A.; Hamachi, I. J. Am. Chem. Soc. 2007, 129, 15777.
31. (a) Beatty, K. E.; Xie, F.; Wang, Q.; Tirrell, D. A. J. Am. Chem. Soc. 2005, 127, 14150.
32. (b) Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. H.; Carell, T. Org. Lett. 2006, 8, 3639.
33. (c) Jawalekar, A. M.; Cremers Meeuwenoord, N. J. (S.) G. O.; Overkleeft, H. S. Van der Marel, G. S.; Rutjes, F. P. J. T.; Van Delft, F. L. J. Org. Chem. 2008, 73, 287.
34. (d) Haensch, C.; Hoeppener, S.; Schubert, U. S. Nanotechnology 2008, 19, 035703 (7pp).
35. (e) Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. Org. Lett. 2004, 6, 4603.
36. (f) Zhou, Z.; Fahrni, C. J. J. Am. Chem. Soc. 2004, 126, 8862.
37. (a) Bernardi, D.; Ba, L.A.; Kirsch, G. Synthesis 2007, 140.
38. (b) Bernardi, D.; Battaglia, E.; Kirsch, G. Bioorg. Med. Chem. Lett. 2006, 16, 1601.
39. (c) Bernardi, D.; Dicko, A.; Kirsch, G. Synthesis 2006, 509.
40. Dorman, G.; Prestwich, G. D. Biochemistry 1994, 33, 5661.
41. Singh, A.; Thornton, E. R.; Westheimer, F. H. J. Biol. Chem. 1962, 237, PC3006.
42. (a) Rodríguez-Domínguez, J. C.; Kirsch, G. Synthesis 2006, 1895.
43. (b) Rodríguez-Domínguez, J. C.; Kirsch, G. Tetrahedron Lett. 2006, 47, 3279.
44. (a) Hatano, B.; Kadokawa, J.; Tagaya, H. Tetrahedron Lett. 2002, 43, 5859.
45. (b) Wang, D.; Zhang, Z. Org. Lett 2003, 5, 4645.
46. (c) Repichet, S.; Le Roux, C.; Roquesb, N.; Dubaca, J. Tetrahedron Lett. 2003, 44, 2037.
47. (d) Urawaa, Y.; Ogurab, K. Tetrahedron Lett. 2003, 44, 271.
48. (e) Molander, G. A.; Yun, C.-S.; Ribagorda, M.; Biolatto, B. J. Org. Chem. 2003, 68, 5534.
49. (f) Kan, T.; Tominari, Y.; Rikimaru, K.; Morohashi, Y.; Natsugari, H.; Tomita, T.; Iwatsubo, T.; Fukuyama, T. Bioorg. Med. Chem. Lett. 2004, 14, 1983.
50. (g) Sarvari, M. H.; Sharghi, H. J. Org. Chem. 2004, 69, 6953.
51. (h) Matsushita, Y.; Sugamoto, K.; Matsui, T. Tetrahedron Lett. 2004, 45, 4723.
52. (i) Zhou, C.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 2302.
53. (j) Gopalakrishnan, M.; Sureshkumar, P.; Kanagarajan, V.; Thanusu, J. Catalysis Commun. 2005, 6, 753.
54. (k) Kang, O.; Luo, J.; Bai, Y.; Yang, Z.; Lei, Z. J. Organomet. Chem. 2005, 690, 6309.
55. (l) Bandgar, B. P.; Patil, A. V. Tetrahedron Lett. 2005, 46, 7627.
56. (m) Kangani, C. O.; Kelleya, D. E.; Day, B. W. Tetrahedron Lett. 2006, 47, 6289.
57. (n) Xing, D.; Guan, B.; Cai, G.; Fang, Z.; Yang, L.; Shi, Z. Org. Lett. 2006, 8, 693.
58. (o) Jang, D. O.; Moon, K. S.; Choa, D. H.; Kim, J.-G. Tetrahedron Lett. 2006, 47, 6063.
59. (p) Xin, B.; Zhang, Y.; Cheng, K J. Org. Chem. 2006, 71, 5725.
60. (a) Takeda, Y.; Kumazawa, T. Bull. Chem. Soc. Japan, 1988, 61, 455.
61. (b) Kang, S.-K.; Ryu, H-C.; Lee, S-W. J. Organomet. Chem. 2000, 610, 38.
62. (c) Rahman, O.; Kihlberg, T.; Langström, B. Eur. J. Org. Chem. 2004, 474.
63. (d) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Croatica Chemica Acta, 2004, 77, 175.
64. (e) De Martino, G.; La Regina, G.; Di Pasquali, A.; Ragno, R.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2005, 48, 4378.
65. (f) Rieke, R. D.; Suha, Y. S.; Kim, S.-H. Tetrahedron Lett. 2005, 46, 5961.
66. (g) Polackova, V.; Toma, S.; Augustinova, I. Tetrahedron 2006, 62, 11675.
67. (a) Futatsuya, F.; Yamane, N.; Ito, K.; Yamada, O.; Fujii, Y.; Ishida, S. German Patent 2,503,216, 1975; Chem. Abstr., 1975, 83, 173933y.
68. (b) Noto, R.; Gruttadauria, M.; LoMeo, P.; Spinelli, D. Collection Czechoslovak Chem. Commun. 1999, 64, 1893.
69. Dey, B. B. J. Chem. Soc., Trans. 1915, 107, 1606.
70. Rodighiero, P.; Manzini, P.; Pastorini, G.; Bordin, F.; Guiotto, A. J. Heterocycl. Chem. 1987, 24, 485.