Click chemistry and medicinal chemistry: A case of "Cyclo- addiction"

ChemMedChem

Volumn 3, Issue 5, 2008, Pages 715-723

  Moorhouse, A D ^a   Moses, J E ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Click chemistry; Cycloaddition; Drug discovery; Medicinal chemistry

Indexed keywords

COPPER;

CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; DRUG DESIGN; REVIEW;

CATALYSIS; CHEMISTRY, PHARMACEUTICAL; COMBINATORIAL CHEMISTRY TECHNIQUES; COPPER; CYCLIZATION; DRUG DESIGN;

EID: 47649133089     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200700334     Document Type: Short Survey

References (56)

1. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075;
2. Angew. Chem. Int. Ed. 2001, 40, 2004-2021.
3. The question was discussed in K. B. Sharpless's talk at the Eighth Tetrahedron Symposium 50th Anniversary Meeting in Berlin, June 27-29, 2007.
4. a) J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249-1262;
5. b) P. Ball, Chem. World 2007, 4, 46-48;
6. c) J. F. Lutz, Angew. Chem. 2007, 119, 1036-1043;
7. Angew. Chem. Int. Ed. 2007, 46, 1018-1025;
8. d) A. Dondoni, Chem. Asian J. 2007, 2, 700-708;
9. e) Y. L. Angell, K. Burgess, Chem. Soc. Rev. 2007, 36, 1674-1689;
10. f) M. V. Gil, M. J. Arevalo, O. Lopez, Synthesis 2007, 1589-1620;
11. g) P. Wu, V. V. Fokin, Aldrichimica Acta 2007, 40, 7-17;
12. h) W. H. Binder, C. Kluger, Curr. Org. Chem. 2006, 10, 1791-1815;
13. i) V. D. Bock, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2006, 51-68.
14. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1137.
15. J. Xie, C. T. Seto, Bioorg. Med. Chem. 2007, 15, 458-473.
16. a) P. B. Alper, S.-C. Hung, C.-H. Wong, Tetrahedron Lett. 1996, 37, 6029-6032;
17. b) H. S. G. Beckmann, V. Wittmann, Org. Lett. 2007, 9, 1-4.
18. P. Appukkuttan, W. Dehaen, V. V. Fokin, E. Van der Eycken, Org. Lett. 2004, 6, 4223-4225.
19. K. Barral, A. D. Moorhouse, J. E. Moses, Org. Lett. 2007, 9, 1809-1811.
20. J. Li, M. Zheng, W. Tang, P-L. He, W. Zhu, T. Li, J-P. Zuo, H. Liu, H. Jiang, Bioorg. Med. Chem. Lett. 2006, 16, 5009-5013.
21. B.-C. Suh, H. Jeon, G. H. Posner, S. M. Silverman, Tetrahedron Lett. 2004, 45, 4623-4625.
22. P. L. Suarez, Z. Gándara, G. Gómez, Y. Fall, Tetrahedron Lett. 2004, 45, 4619-4621.
23. C. Petchprayoon, K. Suwanborirux, R. Miller, T. Sakata, G. Marriott, J. Nat. Prod. 2005, 68, 157-161.
24. X. Fu, C. Albermann, C. Zhang, J. S. Thorson, Org. Lett. 2005, 7, 1513-1515.
25. G. Zhang, L. Fang, L. Zhu, D. Sun, P. G. Wang, Bioorg. Med. Chem. 2006, 14, 426-434.
26. S. Quader, S. E. Boyd, I. D. Jenkins, T. A. Houston, J. Org. Chem. 2007, 72, 1962-1979.
27. S. Löber, P. Rodriguez-Loaiza, P. Gmeiner, Org. Lett. 2003, 5, 1753-1755.
28. P. Rodriguez-Loaiza, S. Löber, H. Hübner, P. Gmeiner, Bioorg. Med. Chem. 2007, 15, 7248-7257.
29. P. Rodriguez-Loaiza, S. Löber, H. Hübner, P. Gmeiner, J. Comb. Chem. 2006, 8, 252-261.
30. For a review see: A. B. Beeler, S. E. Schaus, J. A. Porco, Jr., Curr. Opin. Chem. Biol. 2005, 9, 277-284.
31. R. Srinivasan, M. Uttamchandani, S. Q. Yao, Org. Lett. 2006, 8, 713-716.
32. J. Wang, M. Uttamchandani, J. Li, M. Hu, S. Q. Yao, Org. Lett. 2006, 8, 3821-3824.
33. A. Brik, C.-Y. Wu, C.-H. Wong, Org. Biomol. Chem. 2006, 4, 1446-1457.
34. L. V. Lee, M. L. Mitchell, S.-J. Huang, V. V. Fokin, K. B. Sharpless, C.-H. Wong, J. Am. Chem. Soc. 2003, 125, 9588-9589.
35. A. Brik, J. Muldoon, Y.-C. Lin, J. H. Elder, D. S. Goodsell, A. J. Olson, V. V. Fokin, K. B. Sharpless, C.-H. Wong, ChemBioChem 2003, 4, 1246-1248.
36. a) I. Huc, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 1997, 94, 2106-2110;
37. b) J.-M. Lehn, Chem. Eur. J. 1999, 5, 2455-2463;
38. c) S. Otto, R. L. E. Furlan, J. K. M. Sanders, Drug Discovery Today 2002, 7, 117-125.
39. S. E. Greasley, T. H. Marsilje, H. Cai, S. Baker, S. J. Benkovic, D. L. Boger, I. A. Wilson, Biochemistry 2001, 40, 13538-13547.
40. a) W. L. Mock, T. A. Irra, J. P. Wepsiec, T. L. Manimaran, J. Org. Chem. 1983, 48, 3619-3620;
41. b) W. L. Mock, T. A. Irra, J. P. Wepsiec, M. Adhya, J. Org. Chem. 1989, 54, 5302-5308;
42. c) W. L. Mock, Top. Curr. Chem. 1995, 175, 1-24.
43. W. G. Lewis, L. G. Green, F. Grynszpan, Z. Radiæ, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless, Angew. Chem. 2002, 114, 1095-1099;
44. Angew. Chem. Int. Ed. 2002, 41, 1053-1057.
45. M. Whiting, J. Muldoon, Y.-C. Lin, S. M. Silverman, W. Lindstrom, A. J. Olson, H. C. Kolb, M. G. Finn, K. B. Sharpless, J. H. Elder, V. V. Fokin, Angew. Chem. 2006, 118, 1463-1467;
46. Angew. Chem. Int. Ed. 2006, 45, 1435-1439.
47. J. Wang, G. Sui, V. P. Mocharla, R. J. Lin, M. E. Phelps, H. C. Kolb, H.-R. Tseng, Angew. Chem. 2006, 118, 5402-5407;
48. Angew. Chem. Int. Ed. 2006, 45, 5276-5281.
49. G. C. Tron, T. Pirali, R. A. Billington, P. L. Canonico, G. Sorba, A. A. Genazzani, Med. Res. Rev. 2007, DOI: 10.1002/med.20107.
50. A. D. Moorhouse, A. M. Santos, M. Gunaratnam, M. Moore, S. Neidle, J. E. Moses, J. Am. Chem. Soc. 2006, 128, 15972-15973.
51. a) R. V. Somu, H. Boshoff, C. Qiao, E. M. Bennett, C. E. Barry III, C. C. Aldrich, J. Med. Chem. 2006, 49, 31-34;
52. b) F. Pagliai, T. Pirali, E. Del Grosso, R. Di Brisco, G. C. Tron, G. Sorba, A. A. Genazzani, J. Med. Chem. 2006, 49, 467-470.
53. S. Kim, M. Cho, T. Lee, S. Lee, H-Y. Min, S. K. Lee, Bioorg. Med. Chem. Lett. 2007, 17, 4584-4587.
54. A. Brik, J. Alexandratos, Y. -C, Lin, J. H. Elder, A. J. Olson, A. Wlodawer, D. S. Goodsell, C.-H. Wong, ChemBioChem 2005, 6, 1167-1169.
55. W. J. Choi, Z.-D. Shi, K. M. Worthy, L. Bindu, R. G. Karki, M. C. Nicklaus, R. J. Fisher, T. B. Burke, Jr., Bioorg. Med. Chem. Lett. 2006, 16, 5265-5269.
56. J. Chen, Z. Nikolovska-Coleska, C.-H. Yang, C. Gomez, W. Gao, K. Krajewski, S. Jiang, P. Roller, S. Wang, Bioorg. Med. Chem. Lett. 2007, 17, 3939-3942.