General solid-phase method for the preparation of mechanism-based cysteine protease inhibitors

Journal of the American Chemical Society

Volumn 121, Issue 43, 1999, Pages 9907-9914

  Lee, Alice ^a   Huang, Lily ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE PROTEINASE INHIBITOR;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION;

EID: 0033520777     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992009a     Document Type: Article

References (30)

1. For a review on cysteine proteases and their inhibitors, see: Otto, H.-H.; Schirmeister, T. Chem. Rev. 1997, 97, 133-171.
2. Suzuki, K.; Sorimachi, H. FEBS Lett. 1998, 433, 1-4.
3. Bossard, M. J.; Tomaszek, T. A.; Thompson, S. K.; Amegadzie, B. Y.; Hanning, C. R.; Jones, C.; Kurdyla, J. T.; McNulty, D. E.; Drake, F. H.; Gowen, M.; Levy, M. A. J. Biol. Chem. 1996, 271, 12517-12524.
4. Thornberry, N. A. Chem. Biol. 1998, 5, R97-R103.
5. See also the Symposium-in-Print on cysteine protease inhibitors featured in Bioorg. Med. Chem. 1999, 7, 571-644.
6. (a) Marquis, R. W.; Ru, Y.; Yamashita, D. S.; Oh, H.-J.; Yen, J.; Thompson, S. K.; Carr, T. J.; Levy, M. A.; Tomaszek, T. A.; Ijames, C. F.; Smith, W. W.; Zhao, B.; Janson, C. A.; Abdel-Meguid, S. S.; D'Alessio, K. J.; McQueney, M. S.; Veber, D. F. Bioorg. Med. Chem. 1999, 7, 581-588.
7. (b) Yamashita, D. S.; Smith, W. W.; Zhao, B.; Janson, C. A.; Tomaszek, T. A.; Bossard, M. J.; Levy, M. A.; Oh, H.; Carr, T. J.; Thompson, S. K.; Ijames, C. F.; Carr, S. A.; McQueney, M.; D'Alessio, K. J.; Amegadzie, B. Y.; Hanning, C. R.; Abdel-Meguid, S.; DesJarlais, R. L.; Gleason, J. G.; Veber, D. F. J. Am. Chem. Soc. 1997, 119, 11351-11352.
8. (a) Mjalli, A. M.; Chapman, K. T.; Zhao, J. J.; Thornberry, N. A.; Peterson, E. P.; MacCoss, M. Bioorg. Med. Chem. Lett. 1995, 5, 1405-1408.
9. (b) Mjalli, A. M.; Chapman, K. T.; MacCoss, M.; Thornberry, N. A.; Peterson, E. P. Bioorg. Med. Chem. Lett. 1994, 4, 1965-1968.
10. (a) Krantz, A.; Copp, L. J.; Coles, P. J.; Smith, R. A.; Heard, S. B. Biochemistry 1991, 30, 4678-4687.
11. (b) Pliura, D. H.; Bonaventura, B. J.; Smith, R. A.; Coles, P. J.; Krantz, A. Biochem. J. 1992, 288, 759-762.
12. (c) Graybill, T. L.; Prouty, C. P.; Speier, G. J.; Hoyer, D.; Dolle, R. E.; Helaszek, C. T.; Ator, M. A.; Uhl, J.; Strasters, J. Bioorg. Med. Chem. Lett. 1997, 7, 41-46.
13. Whittaker, M. Curr. Opin. Chem. Biol. 1998, 2, 386-396.
14. (a) Lee, C. E.; Kick, E. K.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 9735-9747.
15. (b) Kick, E. K.; Roe, D. C.; Skillman, A. G.; Liu, G.; Ewing, T. J. A.; Sun, Y.; Kuntz, I. D.; Ellman, J. A. Chem. Biol. 1997, 4, 297-307.
16. Rano, T. A.; Timkey, T.; Peterson, E. P.; Rotonda, J.; Nicholson, D. W.; Becker, J. W.; Chapman, K. T.; Thornberry, N. A. Chem. Biol. 1997, 4, 149-155.
17. Yamashita, D. S.; Dong, X.; Oh, H.-J.; Brook, C. S.; Tomaszek, T. A.; Szewcsuk, L.; Tew, D. G.; Veber, D. F. J. Comb. Chem. 1999, 1, 207-215.
18. See also: Lee, A.; Huang, L.; Ellman, J. A. Presented at the 217th National Meeting of the American Chemical Society, Anaheim, CA, March 1999; poster ORGN 213.
19. For a review on azodiene chemistry, see: Attanasi, O. A.; Filippone, P. Synlett 1997, 1128-1140.
20. Murphy, A. M.; Dagnino, R.; Vallar, P. L.; Trippe, A. J.; Sherman, S. L.; Lumpkin, R. H.; Tamura, S. Y.; Webb, T. R. J. Am. Chem. Soc. 1992, 114, 3156-3157.
21. (a) Krantz, A.; Copp, L. J.; Smith, R. A.; Heard, S. B. Biochemistry 1991, 30, 4678-4687.
22. (b) Dolle, R. E.; Hoyer, D.; Prasad, C. V. C.; Schmidt, S. J.; Helaszek, C. T.; Miller, R. E.; Ator, M. A. J. Med. Chem. 1994, 37, 563-564.
23. An analogous procedure with 4-nitrophenylchloroformate provided lower loading of the linker on support.
24. Site-site interactions on solid support have been well-documented in literature. (a) Bhargava, K. K.; Sarin, V. K.; Trang, N. L.; Cerami, A.; Merrifield, R. B. J. Am. Chem. Soc. 1983, 105, 3247-3251. (b) Scott, L. T.; Rebek, J.; Ovsyanko, L.; Sims, C. L. J. Am. Chem. Soc. 1977, 99, 625-626.
25. Site-site interactions on solid support have been well-documented in literature. (a) Bhargava, K. K.; Sarin, V. K.; Trang, N. L.; Cerami, A.; Merrifield, R. B. J. Am. Chem. Soc. 1983, 105, 3247-3251. (b) Scott, L. T.; Rebek, J.; Ovsyanko, L.; Sims, C. L. J. Am. Chem. Soc. 1977, 99, 625-626.
26. Shapiro, G.; Buechler, D. Tetrahedron Lett. 1994, 35, 5421-5424.
27. Guibé, F. Tetrahedron 1998, 54, 2967-3042.
28. Lombardi, P. Chem. Ind. 1990, 708.
29. Coulson, D. R. Inorg. Synth. 1972, 121-124.
30. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2927.