Expanding the chemical space in practice: Diversity-oriented synthesis

Combinatorial Chemistry and High Throughput Screening

Volumn 11, Issue 8, 2008, Pages 587-601

  Peuchmaur, Marine ^a   Wong, Yung Sing ^a  

^a Université Joseph Fourier   (France)

Author keywords

Chemical space; Complexity; Diversity; Diversity oriented synthesis; Multicomponent reactions; Skeletal divergent reactions; Small molecules; Stereodivergent reactions

Indexed keywords

DIVERSITY ORIENTED SYNTHESIS; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 51349097910     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620708785739916     Document Type: Review

References (83)

1. Stockwell, B.R. Nature, 2004, 432, 846.
2. Schreiber, S.L. Bioorg. Med. Chem., 1998, 6, 1127.
3. Mitchison, T.J. Chem. Biol., 1994, 1, 3.
4. Walsh, D.P.; Chang, Y.-T. Chem. Rev., 2006, 106, 2476.
5. Schreiber, S.L.; Kapoor, T.M.; Wess, G. Chemical Biology, Wiley-VCH:Weinheim, 2007.
6. Class, S. Chem. Eng. News, 2002, 80, 39.
7. Macarron, R. Drug Discov. Today, 2006, 11, 277.
8. Breinbauer, R.; Vetter, I.R.; Waldmann, H. Angew. Chem. Int. Ed., 2002, 41, 2878.
9. Newman, D.J.; Gragg, G.M.; Snader, K.A. J. Nat. Prod., 2003, 66, 1022.
10. Butler, M.S. J. Nat. Prod., 2004, 67, 2141.
11. Clardy, J.; Walsh, C. Nature, 2004, 432, 829.
12. Piggott, A.M.; Karuso, P. Comb. Chem. High Throughput Screen., 2004, 7, 607.
13. Ortholand, J.-Y.; Ganesan, A. Curr. Opin. Chem. Biol., 2004, 8, 271.
14. Reayi, A.; Arya, P. Curr. Opin. Chem. Biol., 2005, 9, 240.
15. Dobson, C.M. Nature, 2004, 432, 824.
16. Haggarty, S.J. Curr. Opin. Chem. Biol., 2005, 9, 296.
17. Bohacek, R.S.; McMartin, C.; Guida, W.C. Med. Res. Rev., 1996, 16, 3.
18. Schreiber, S.L. Science, 2000, 287, 1964.
19. Burke, M.D.; Schreiber, S.L. Angew. Chem. Int. Ed., 2004, 43, 46.
20. Schreiber, S.L. Chem. Eng. News, 2003, 81, 51.
21. Selzer, P.; Roth, H.-J.; Ertl, P.; Schuffenhauer, A. Curr. Opin. Chem. Biol., 2005, 9, 310.
22. Shelat, A.A.; Guy, R.K. Curr. Opin. Chem. Biol., 2007, 11, 244.
23. Spring, D.R. Org. Biomol. Chem., 2003, 1, 3867.
24. Spring, D.R. Chem. Soc. Rev., 2005, 34, 472.
25. Shang, S.; Tan, D.S. Curr. Opin. Chem. Biol., 2005, 9, 248.
26. Tan, D.S. Nat. Chem. Biol., 2005, 1, 74.
27. Thomas, G.L.; Wyatt, E.E.; Spring, D.R. Curr. Opin. Drug Discov. Devel., 2006, 9, 700.
28. Hertz, S.H. J. Am. Chem. Soc., 1981, 103, 3599.
29. Barone, R.; Chanon, M. J. Chem. Inf. Comput. Sci., 2001, 41, 269.
30. Bertz, S.H. New. J. Chem., 2003, 27, 870.
31. Rücker C.; Rücker G.; Bertz S.H. J. Chem. Inf. Comput. Sci., 2004, 44, 378.
32. Blackwell, H.E.; Pérez, L.; Stavenger, R.A.; Tallarico, J.A.; Cope Eatough, E.; Foley, M.A.; Schreiber, S.L. Chem. Biol., 2001, 8, 1167.
33. Clemons, P.A.; Koehler, A.N.; Wagner, B.K.; Sprigings, T.G.; Spring, D.R.; King, R.W.; Schreiber, S.L.; Foley, M.A. Chem. Biol., 2001, 8, 1183.
34. Zhu, J.; Bienaymé, H. Multicomponent Reactions, Wiley-VCH: Weinheim, 2005.
35. Ramón, D.J.; Yus, M. Angew. Chem. Int. Ed., 2005, 44, 1602.
36. Neumann, H.; Jacobi von Wangelin, A.; Gördes, D.; Spannenberg, A.; Belief, M. J. Am. Chem. Soc., 2001, 123, 8398.
37. Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Belief, M. Chem. Eur. J., 2003, 9, 4286.
38. Hübner, S.; Neumann, H.; Jacobi von Wangelin, A.; Klaus, S.; Strübing, D; Klein, H.; Beller, M. Synthesis, 2005, 2084.
39. skel = 1), the two kind of reactions will result in the same number of potential products.
40. Tejedor, D.; García-Tellado, F. Chem. Soc. Rev., 2007, 36, 484.
41. Hübner, S.; Jiao, H.; Michalik, D.; Neumann, H.; Klaus, S.; Strübing, D.; Spannenberg, A.; Beller, M. Chem. Asian J., 2007, 2, 720.
42. Hübner, S.; Michalik, D.; Jiao, H.; Neumann, H.; Klaus, S.; Strübing, D.; Spannenberg, A.; Beller, M. Chem. Asian J., 2007, 2, 734.
43. Powell, D.A.; Batey, R.A. Org. Lett., 2002, 4, 2913.
44. Pavarov, S.L. Russ. Chem. Rev., 1967, 36, 656.
45. Simon, C.; Liéby-Muller, F.; Peyronel, J.-F.; Constantieux, T.; Rodriguez, J. Synlett, 2003, 2301.
46. Liéby-Muller, F.; Simon, C.; Constantieux, T.; Rodriguez, J. QSAR Comb. Sci., 2006, 25, 432.
47. Gommermann, N.; Koradin, C.; Polborn, K.; Knochel, P. Angew. Chem. Int. Ed., 2003, 42, 5763.
48. Gommermann, N. Knochel, P. Chem. Eur. J., 2006, 12, 4380.
49. Taylor A.M.; Schreiber, S.L. Org. Lett., 2006, 8, 143.
50. Passerini, M.; Sirnone, L. Gazz. Chim. Ital., 1921, 51, 126.
51. Passerini, M.; Ragni, G. Gazz. Chim. Ital., 1931, 61, 964.
52. Denmark, S.E.; Fan, Y. J. Am. Chem. Soc., 2003, 125, 7825.
53. Denmark, S.E.; Fan, Y. J. Org. Chem., 2005, 70, 9667.
54. Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Dömling, A. Org. Lett., 2003, 5, 4021.
55. Andreana, P.R.; Liu, C.C.; Schreiber, S.L. Org. Lett., 2004, 6, 4231.
56. Sebahar, P.R.; Williams, R.M. J. Am. Chem. Soc., 2000, 122, 5666.
57. Lo M.M.-C.; Neumann, C.S.; Nagayama, S.; Perlstein, E.O.; Schreiber, S.L. J. Am. Chem. Soc., 2004, 126, 16077.
58. Chavez, D.E.; Jacobsen, E.N. Org. Lett., 2003, 5, 2563.
59. Evans, D.A.; Côté, B.; Coleman, P.J.; Connell, B.T. J. Am. Chem. Soc., 2003, 125, 10893.
60. Evans, D.A.; Dart, M.J.; Duffy, J.L.; Yang, M.G. J. Am. Chem. Soc., 1996, 118, 4322.
61. Petasis, N.A.; Zavialov, I.A. J. Am. Chem. Soc., 1997, 119, 445.
62. Petasis, N.A.; Zavialov, LA. J. Am. Chem. Soc., 1998, 120, 11798.
63. Kumagai, N.; Muncipinto, G.; Schreiber, S.L. Angew. Chem. Int. Ed., 2006, 45, 3635.
64. Stavenger, R.A.; Schreiber, S.L. Angew. Chem. Int. Ed., 2001, 40, 3417.
65. Rondot, C.; Zhu, J. Org. Lett., 2005, 7, 1641.
66. Burke, M.D.; Berger, E.M.; Schreiber, S.L. Science, 2003, 302, 613.
67. Burke, M.D.; Berger, E.M.; Schreiber, S.L. J. Am. Chem. Soc., 2004, 126, 14095.
68. Achmatowicz, O.; Bukowski, P.; Szechner, B. Zwierzchowska, Z.; Zamojski, A. Tetrahedron, 1971, 27, 1973.
69. Beeler, A.B.; Su, S.; Singleton, C.A.; Porco, J.A. J. Am. Chem. Soc., 2007, 129, 1413.
70. Ugi, I.; Steinbrückner, C. Angew. Chem., 1959, 71, 386.
71. Ugi, I.; Steinbrückner, C. Angew. Chem., 1960, 72, 267.
72. Sello, J.K.; Andreana, P.R.; Lee, D.; Schreiber, S.L. Org. Lett., 2003, 5, 4125.
73. Paulvannan, K. Tetrahedron Lett., 1999, 40, 1851.
74. Lee, D.; Sello, J.K; Schreiber, S.L. Org. Lett., 2000, 2, 709.
75. Kumar, N.; Kiuchi, M.; Tallarico, J.A.; Schreiber, S.L. Org. Lett., 2005, 7, 2535.
76. Schomberg, D.; Thielmann, M.; Winterfeldt, E. Tetrahedron Lett., 1985, 26, 1705.
77. Prelle, A.; Winterfeldt, E. Heterocycles, 1989, 28, 333.
78. Mehta, G.; Singh, V. Chem. Soc. Rev., 2002, 31, 324.
79. Tietze, L.F.; Bell, H.P.. Chandrasekhar, S. Angew. Chem. Int. Ed., 2003, 42, 3996.
80. Chen, C.; Li, X.; Neumann, C.S.; Lo, M.M.-C.; Schreiber, S.L. Angew. Chem. Int. Ed., 2005, 44, 2249.
81. Chen. C.; Li. X.; Schreiber, S.L. J. Am. Chem. Soc., 2003, 125, 10174.
82. Spiegel, D.A.; Schroeder, F.C.; Duvall, J.R.; Schreiber, S.L. J. Am. Chem. Soc., 2006, 128, 14766.
83. Ulaczyk-Lesanko, A.; Hall, D.G. Curr. Opin. Chem. Biol., 2005, 9, 266.