Microwave-assisted "libraries from libraries" approach toward the synthesis of allyl- and c-cyclopropylalkylamides

Journal of Combinatorial Chemistry

Volumn 7, Issue 2, 2005, Pages 322-330

  Wipf, Peter ^a   Coleman, Claire M ^a   Janjic, Jelena M ^a   Iyer, Pravin S ^a   Fodor, Matthew D ^a   Shafer, Yvonne A ^a   Stephenson, Corey R J ^a   Kendall, Christopher ^a   Day, Billy W ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBAMIC ACID; ESTROGEN RECEPTOR ALPHA; LEAD; METHANE; SULFONAMIDE; TAMOXIFEN;

AQUEOUS SOLUTION; ARTICLE; BIOLOGICAL ACTIVITY; COMBINATORIAL LIBRARY; EVALUATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

ALLYL COMPOUNDS; AMIDES; BINDING, COMPETITIVE; COMBINATORIAL CHEMISTRY TECHNIQUES; ESTROGEN RECEPTOR ALPHA; MICROWAVES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 17144395529     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049842a     Document Type: Article

References (43)

1. Dolle, R. E. J. Comb. Chem. 2004, 6, 623-679.
2. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
3. Altorfer, M.; Ermert, P.; Faessler, J.; Farooq, S.; Hillesheim, E.; Jeanguenat, A.; Klumpp, K.; Maienfisch, P.; Martin, J. A.; Merrett, J. H.; Parkes, K. E. B.; Obrecht, J.-P.; Pitterna, T.; Obrecht, D. Chimia 2003, 57, 262-269.
4. (a) Baxendale, I. R.; Ley, S. V. Nat. Rev. Drug Discovery 2002, 1, 573-586.
5. (b) Kirschning, A.; Monenschein, H.; Wittenberg, R. Angew. Chem., Int. Ed. 2001, 40, 650-679.
6. Lam, K. S.; Salmon, S. E.; Hersh, E. M.; Hruby, V. J.; Kazmierski, W. M.; Knapp, R. J. Nature 1991, 354, 82-84.
7. (a) Brohm, D.; Metzger, S.; Bhargava, A.; Müller, O.; Lieb, F.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 307-311.
8. (b) Pelish, H. E.; Westwood, N. J.; Feng, Y.; Kirchhausen, T.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 6740-6741.
9. (c) Lee, M.-L.; Schneider, G. J. Comb. Chem. 2001, 3, 284-289.
10. (d) Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391-9395.
11. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G.-Q.; Affleck, R. L.; Lillig, J. E. J. Am. Chem. Soc. 2000, 122, 9954-9967.
12. (a) Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 46-58.
13. (b) Wipf, P.; Stephenson, C. R. J.; Walczak, M. A. A. Org. Lett. 2004, 6, 3009-3012.
14. (c) Spring, D. R. Org. Biomol. Chem. 2003, 1, 3867-3870.
15. van de Waterbeemd, H.; Gifford, E. Nat. Rev. Drug Discovery 2003, 2, 192-204.
16. Ostresh, J. M.; Husar, G. H.; Blondelle, S. E.; Dorner, P. A.; Weber, R. A.; Houghten, R. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11138-11142.
17. (a) Blackwell, H. E. Org. Biomol. Chem. 2003, 1, 1251-1269.
18. (b) Lew, A.; Krutzik, P. O.; Hart, M. E.; Chamberlin, A. R. J. Comb. Chem. 2002, 4, 95-105.
19. (a) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2003, 125, 761-768.
20. (b) Wipf, P.; Kendall, C. Chem. Eur. J. 2002, 8, 1778-1784.
21. (c) Wipf, P.; Kendall, C. Org. Lett. 2001, 3, 2773-2776.
22. (d) Wipf, P.; Kendall, C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2001, 123, 5122-5123.
23. Janjic, J. M.; Mu, Y.; Kendall, C.; Stephenson, C. R. J.; Balachandran, R.; Raccor, B. S.; Lu, Y.; Zhu, G.; Xie, W.; Wipf, P.; Day, B. W. Bioorg. Med. Chem. 2005, 13, 157-164.
24. Wipf, P.; Nunes, R. L. Tetrahedron 2004, 60, 1269-1279.
25. (a) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853-12910.
26. (b) Wipf, P.; Kendall, C. In Topics in Organometallic Chemistry; Takahashi, T., Ed.; Springer-Verlag: Berlin, 2004; Vol. 8, pp 1-25.
27. A preliminary communication on the use of microwaves to accelerate allylic amide formation has recently been published: Wipf, P.; Janjic, J.; Stephenson, C. R. J. Org. Biomol. Chem. 2004, 2, 443-445. For the use of microwaves to enhance the cross-coupling of zirconocenes, see: Lipshutz, B. H.; Frieman, B. Tetrahedron 2004, 60, 1309-1316.
28. A preliminary communication on the use of microwaves to accelerate allylic amide formation has recently been published: Wipf, P.; Janjic, J.; Stephenson, C. R. J. Org. Biomol. Chem. 2004, 2, 443-445. For the use of microwaves to enhance the cross-coupling of zirconocenes, see: Lipshutz, B. H.; Frieman, B. Tetrahedron 2004, 60, 1309-1316.
29. Hydrozirconation of internal alkynes is highly regioselective if thermodynamic conditions are used and if the steric hindrance of the substituents at the triple bond is significantly different; see refs 14 and 15.
30. Since the biological activity of both enantiomers of lead structure 1 was equivalent (see ref 12), compounds in this work were prepared in racemic form.
31. (a) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769-3772.
32. (b) Fisher, R. P.; On, H. P.; Snow, J. T.; Zweifel, G. Synthesis 1982, 127-129.
33. Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561-5568.
34. Pinho, P.; Andersson, P. G. Tetrahedron 2001, 57, 1615-1618.
35. Boyd, D. R.; Malone, J. F.; McGuckin, M. R.; Jennings, W. B.; Rutherford, M.; Saket, B. M. J. Chem. Soc., Perkin Trans 2 1988, 1145-1150.
36. N-Tosylimines can also be used in this reaction sequence. However, the tosyl group is considerably more difficult to remove. See, for example, ref 11.
37. Ramage, R.; Hopton, D.; Parrott, M. J.; Kenner, G. W.; Moore, G. A. J. Chem. Soc., Perkin Trans. 1 1984, 1357-1370.
38. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3-25.
39. Wenlock, M. C.; Austin, R. P.; Barton, P.; Davis, A. M.; Leeson, P. D. J. Med. Chem. 2003, 46, 1250-1256.
40. Parker, G. J.; Law, T. L.; Lenoch, F. J.; Bolger, R. E. J. Biomol. Screen. 2000, 5, 77-88.
41. Cory, A. H.; Owen, T. C.; Barltrop, J. A.; Cory, J. G. Cancer Commun. 1991, 3, 207-212.
42. Jorgensen, W. L. Science 2004, 303, 1813-1818.
43. Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1993, 71, 77.