Solution- and solid-phase, modular approaches for obtaining different natural product-like polycyclic architectures from an aminoindoline scaffold for combinatorial chemistry

Journal of Combinatorial Chemistry

Volumn 8, Issue 6, 2006, Pages 856-871

  Reddy, P Thirupathi ^a   Quevillon, S ^a   Gan, Zhonghong ^a   Forbes, Nauzer ^a   Leek, Donald M ^a   Arya, Prabhat ^a,b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CONFORMATION; CYCLIZATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSITIVITY AND SPECIFICITY; SOLUTION AND SOLUBILITY; STEREOISOMERISM; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; POLYCYCLIC COMPOUNDS; SENSITIVITY AND SPECIFICITY; SOLUTIONS; STEREOISOMERISM;

EID: 33845267229     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0600573     Document Type: Article

References (31)

1. (a) Pommier, Y.; Cherfils, J. Trends Pharmacol. Sci. 2005, 26, 139-145.
2. (b) Arkin, M. R.; Wells, J. A. Nat. Rev. Drug Discovery 2004, 3, 301-317.
3. (c) Berg, T. Angew. Chem., Int. Ed. 2003, 42, 2462-2481.
4. (d) Boger, D. L.; Desharnais, J.; Capps, K. Angew. Chem., Int. Ed. 2003, 42, 4138-4176.
5. (a) Schreiber, S. L. Nat. Chem. Biol. 2005, 1, 64-66.
6. Schreiber, S. L. Chem. Eng. News 2003, 81, 51-59.
7. (b) Gura, T. Nature 2000, 407, 282-284.
8. (c) Strausberg, R. L.; Schreiber, S. L. Science 2003, 300, 294-295.
9. (d) Mayer, T. U. Trends Cell Biol. 2003, 13, 270-277.
10. (e) Peterson, J. R.; Mitchison, T. J. Chem. Biol. 2002, 9, 1275-1285.
11. (a) Arya, P.; Roth, H.-J. Curr. Opin. Chem. Biol. 2005, 9, 229-231.
12. (b) Reayi, A.; Arya, P. Curr. Opin. Chem. Biol. 2005, 9, 240-247.
13. (a) Burke, M. D.; Schreiber, S. L. Angew. Chem. Int. Ed. 2004, 43, 46-58.
14. (b) Tan, D. S. Nat. Chem. Biol 2005, 1, 74-80.
15. (c) Borman, S. Chem. Eng. News 2004, 82, 32-40.
16. Arya, P.; R. Joseph, R.; Gan, Z.; Rakic, B. Chem. Biol. 2005, 12, 163-180.
17. Gan, Z.; Reddy, P. T.; Quevillon, S.; Couve-Bonnaire, S.; Arya, P. Angew. Chem., Int. Ed. 2005, 44, 1366-1368.
18. Deweick, P. M. Medicinal Natural Products - A Biosynthetic Approach, 2nd ed.; JohnWiley & Sons, LTD: Chichester, New York, 2002; Chapter 6.
19. (a) See reference 4a.
20. (b) Burke, M. D.; Berger, E. M.; Schreiber, S. L. Science 2003, 302, 613-618.
21. (c) For a recent article on solution and solid phase methods development leading to the library generation of structurally complex and diverse, natural-product-like architectures, see: Mitchell, J. M.; Shaw, J. T. Angew. Chem., Int. Ed. 2006, 46, 1722-1726.
22. Quevillon, S.; MS Thesis, University of Ottawa, May 2003.
23. For the detailed experimental procedure, see the Experimental Section.
24. For a few selected examples of medium-ring synthesis on solid phase, see: (a) Spring, D. R.; Krishnan, S.; Schreiber, S. L. J. Am. Chem. Soc. 2000, 122, 5656-5657.
25. (b) Spring, D. R.; Krishnan, S.; Blackwell, H. E.; Schreiber, S. L. J. Am. Chem. Soc. 2002, 124, 1354-1362.
26. (c) Khadem, S.; Joseph, R.; Rastegar, M.; Leek, D. M.; Udachin, K. A.; Arya, P. J. Comb. Chem. 2004, 6, 724-734.
27. For a few selected examples on the use of small-molecule microarrays, see: (a) Barnes-Seeman, D.; Park, S. B.; Koehler, A. N.; Schreiber, S. L. Angew. Chem., Int. Ed. 2003, 42, 2376-2379.
28. (b) MacBeath, G.; Koehler, A. N.; Schreiber, S. L. J. Am. Chem. Soc. 1999, 121, 7967-7968.
29. (c) Bradner, J. E.; McPherson, O. M.; Mazitschek, R.; Barnes-Seeman, D.; Shen, J. P.; Dhaliwal, J.; Stevenson, K. E.; Duffner, J. L.; Park, S. B.; Neuberg, D. S.; Nghiem, P. T.; Schreiber, S. L.; Koehler, A. N. Chem. Biol. 2006, 13, 493-504.
30. (a) Tallarico, J. A.; Depew, K. M.; Pelish, H. E.; Pestwood, N. J.; Lindsley, C. W.; Shair, M. D.; Schreiber, S. L.; Foley, M. A. J. Comb. Chem. 2001, 3, 312-318.
31. (b) Ralph Mazitschek (Broad Institute of Harvard and MIT) is thanked for providing the revised procedure for the loading.