An Introduction to Diversity-Oriented Synthesis

Linker Strategies in Solid-Phase Organic Synthesis

Volumn , Issue , 2009, Pages 239-262

  Spandl, Richard J ^a   Thomas, Gemma L ^a   Diaz Gavilan, Monica ^a   O'Connell, Kieron M G ^a   Spring, David R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

'biologically oriented synthesis' (BIOS); ABB' three component coupling reaction in diverse scaffold synthesis; Chemical space exploration; Combinatorial libraries synthesis using 'one synthesis one skeleton' approach; De novo library synthesis using DOS; Diversity oriented synthesis (DOS); Enriching chemical space using DOS; Reverse chemical genetics; Structural classification of natural products (SCONP); Subjective nature of 'Diversity'

Indexed keywords

EID: 84890990098     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470749043.ch8     Document Type: Chapter

References (70)

1. Spandl, R. J., Spring, D. R., and Bender, A.; Org. Biomol. Chem. 2008, DOI: 10.1039/B719372F.
2. Spring, D. R.; Org. Biomol. Chem. 2003, 1, 3867.
3. Thomas, G. L., Wyatt, E. E., and Spring, D. R.; Curr. Opin. Drug Discovery Dev. 2006, 9, 700.
4. Haggarty, S. J.; Curr. Opin. Chem. Biol. 2005, 9, 296.
5. Kim, Y. K., Arai, M. A., Arai, T., et al.; J. Am. Chem. Soc. 2004, 126, 14740.
6. Koehler, A. N., Shamji, A. F., and Schreiber, S. L.; J. Am. Chem. Soc. 2003, 125, 8420.
7. Spring, D. R., Krishnan, S., Blackwell, H. E., and Schreiber, S. L.; J. Am. Chem. Soc. 2002, 124, 1354.
8. Kuruvilla, F. G., Shamji, A. F., Sternson, S. M., et al. Nature 2002, 416, 653.
9. Collins, F. S., Lander, E. S., Rogers, J., and Waterston, R. H.; Nature 2004 431, 931.
10. Brent, M. R.; Nat. Rev. Genet. 2008, 9, 62.
11. Spring, D. R.; Chem. Soc. Rev. 2005, 34, 472.
12. Schreiber, S. L.; Bioorg. Med. Chem. 1998, 6, 1127.
13. Schreiber, S. L.; Chem. Eng. News 2003 81, 51.
14. Walsh, D. P., and Chang, Y. T.; Chem. Rev. 2006, 106, 2476.
15. Hopkins, A. L., and Groom, C. R.; Nat. Rev. Drug Discovery 2002 1, 727.
16. Lipinski, C., and Hopkins, A.; Nature 2004 432, 855.
17. Hann, M. M., Leach, A. R., and Harper, G.; J. Chem. Inf. Comput. Sci. 2001, 41, 856.
18. Schuffenhauer, A., Brown, N., Selzer, P., et al.; J. Chem. Inf. Mod. 2006, 46, 525.
19. MacBeath, G.; Genome Biol. 2001, 2, 2005.1.
20. Fergus, S., Bender, A., and Spring, D. R.; Curr. Opin. Chem. Biol. 2005, 9, 304.
21. Perez, J. J.; Chem. Soc. Rev. 2005, 34, 143.
22. Dobson, C. M.; Nature 2004 432, 824.
23. Downs, G. M., Willett, P., and Fisanick, W.; J. Chem. Inf. Comput. Sci. 1994, 34, 1094.
24. Estrada, E., and Uriarte, E.; Curr. Med. Chem. 2001, 8, 1573.
25. Fitzgerald, S. H., Sabat, M., and Geysen, M.; J. Comb. Chem. 2007, 9, 724.
26. Butler, M. S.; Nat. Prod. Rep. 2008, 22, 162.
27. Lam, K. S.; Trends Microbiol. 2007, 15, 279.
28. Feher, M., and Schmidt, J. M.; J. Chem. Inf. Comput. Sci. 2003, 43, 218.
29. Burke, M. D., and Schreiber, S. L.; Angew. Chem. Int. Ed. 2004, 43, 46.
30. Valler, M. J., and Green, D.; Drug Discov. Today 2000 5, 286.
31. Lipinski, C. A., Lombardo, F., Dominy, B. W., and Feeney, P. J.; Adv. Drug Delivery Rev. 1997, 23, 3.
32. Keller, T. H., Pichota, A., and Yin, Z.; Curr. Opin. Chem. Biol. 2006, 10, 357.
33. Abad-Zapatero, C.; Drug Discov. Today 2007 12, 995.
34. Burke, M. D., Berger, E. M., and Schreiber, S. L.; J. Am. Chem. Soc. 2004, 126, 14095.
35. Evans, B. E., Rittle, K. E., Bock, M. G., et al.; J. Med. Chem. 1988, 31, 2235.
36. Reayi, A., and Arya, P.; Curr. Opin. Chem. Biol. 2005, 9, 240.
37. Clardy, J., and Walsh, C., Nature 2004, 432, 829.
38. Ko, S. K., Jang, H. J., Kim, E., and Park, S. B.; Chem. Commun. 2006, 2962.
39. Zhou, C. X., Dubrovsky, A. V., and Larock, R. C.; J. Org. Chem. 2006, 71, 1626.
40. Messer, R., Führer, C. A., Iner, R. H., and Haner, R.;. Curr. Opin. Chem. Biol. 2005, 9, 259.
41. Boldi, A. M., and Dragoli, D. R.; Chemistry on the Interface of Natural Products and Combinatorial Chemistry, in Combinatorial Synthesis of Natural Product-Based Libraries (Ed.: A. M. Boldi), Taylor and Francis/CRC Press, London, 2006.
42. Goess, B. C., Hannoush, R. N., Chan, L. K., et al.; J. Am. Chem. Soc. 2006, 128, 5391.
43. Buckingham, J.; Dictionary of Natural Products (CD ROM), Taylor and Francis/CRC Press, London, 2005.
44. Kaiser, M., Wetzel, S., Kumar, K., and Waldmann, H.; Cell Mol. Life Sci 2008, 1.
45. Koch, M. A., Schuffenhauer, A., Scheck, M., et al.; Proc. Nat. Acad. Sci. U.S.A. 2005, 102, 17272.
46. Dekker, F. J., Koch, M. A., and Waldmann, H.; Curr. Opin. Chem. Biol. 2005, 9, 232.
47. Noren-Muller, A., Reis-Correa, I., Prinz, H., et al.; Proc. Nat. Acad. Sci. USA 2006 103, 10606.
48. Burke, M. D., Berger, E. M., and Schreiber, S. L.; Science 2003 302, 613.
49. Schreiber, S. L.; Science 2000 287, 1964.
50. Kumar, N., Kiuchi, M., Tallarico, J. A., and Schreiber, S. L.; Org. Lett. 2005, 7, 2535.
51. Nielsen, T. E., and Schreiber, S. L.; Angew. Chem. Int. Ed. 2008, 47, 48.
52. Wyatt, E. E., Fergus, S., Galloway, W., et al.; Chem. Commun. 2006, 3296.
53. Thomas, G. L., Spandl, R. J., Glansdorp, F. G., et al.; Angew. Chem. Int. Ed. 2008, DOI: 10.1002/anie.200705415.
54. Chen, C., Li, X. D., and Schreiber, S. L.; J. Am. Chem. Soc. 2003, 125, 10174.
55. Kolb, H. C., Vannieuwenhze, M. S., and Sharpless, K. B.; Chem. Rev. 1994, 94, 2483.
56. Johnson, J. S., and Evans, D. A.; Acc. Chem. Res. 2000, 33, 325.
57. Thomas, G. L., Ladlow, M., and Spring, D. R.; Org. Biomol. Chem. 2004, 2, 1679.
58. Johnson, A. P., Aucken, H. M., Cavendish, S., et al.; J. Antimicrob. Chemother. 2001, 48, 143.
59. Kumagai, N., Muncipinto, G., and Schreiber, S. L.; Angew. Chem. Int. Ed. 2006, 45, 3635.
60. Tejedor, D., Santos-Exposito, A., and Garcia-Tellado, F.; Chem. Eur. J. 2007, 13, 1201.
61. Comer, E., Rohan, E., Deng, L., and Porco, J. A.; Org. Lett. 2007, 9, 2123.
62. Tejedor, D., and Garcia-Tellado, F.; Chem. Soc. Rev. 2007, 36, 484.
63. Oguri, H., and Schreiber, S. L.; Org. Lett. 2005, 7, 47.
64. Sello, J. K., Andreana, P. R., Lee, D. S., and Schreiber, S. L.; Org. Lett. 2003, 5, 4125.
65. Merrifield, R. B.; J. Am. Chem. Soc. 1963, 85, 2149.
66. Dolle, R. E.; J. Comb. Chem. 2005, 7, 739.
67. Jung, N., Weihn, M., and Bräse, S.;. Top. Curr. Chem. 2007, 278, 1.
68. Scott, P. J. H., and Steel, P. G.; Eur. J. Org. Chem. 2006, 2251.
69. Bräse, S., and Schroen, M.;. Angew. Chem. Int. Ed. 1999, 38, 1071.
70. Bräse, S.;. Acc. Chem. Res. 2004, 37, 805.