Design and synthesis of dipeptidyl α',β'-epoxy ketones, potent irreversible inhibitors of the cysteine protease cruzain

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 19, 1998, Pages 2809-2812

  Roush, William R ^a   González, Florenci V ^a   McKerrow, James H ^b   Hansell, Elizabeth ^b  

^a UNIVERSITY OF MICHIGAN   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRUZIPAIN; CYSTEINE PROTEINASE; CYSTEINE PROTEINASE INHIBITOR; DIPEPTIDYL ALPHA',BETA' EPOXYKETONE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITOR INTERACTION; EPOXIDATION; INHIBITION KINETICS; NONHUMAN; PROTEINASE INHIBITION; STEREOCHEMISTRY; TRYPANOSOMA CRUZI; X RAY CRYSTALLOGRAPHY;

CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; DIPEPTIDES; DRUG DESIGN; KETONES; KINETICS; PROTOZOAN PROTEINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

TRYPANOSOMA; TRYPANOSOMA CRUZI;

EID: 0032491264     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00494-6     Document Type: Article

References (38)

1. 1. McKerrow, J. H.; James, M. N. G. In Perspectives in Drug Discovery and Design; Anderson, P. S., Kenyon, G. L., Marshall, G. R., Eds.; ESCOM Science Publishers: Leiden, 1996; Vol. 6.
2. 2. Otto, H.-H.; Schirmeister, T. Chem. Rev. 1997, 97, 133.
3. 3. Miller, D. K. Ann. Rep. Med. Chem. 1996, 31, 249.
4. 4. McKerrow, J. H.; Sun, E.; Rosenthal, P. J.; Bouvier, J. Annu. Rev. Microbiol. 1993, 47, 821.
5. 5. McKerrow, J. H. In Perspec. Drug Discov. Design; P. S. Anderson, G. L. Kenyon and G. R. Marshall, Eds.; ESCOM Science Publishers: Leiden, 1994; Vol. 2; p 437.
6. 6. Eakin, A. E.; McGrath, M. E.; McKerrow, J. H.; Fletterick, R. J.; Craik, C. S. J. Biol. Chem. 1993, 268, 6115.
7. 7. McGrath, M. E.; Eakin, A. E.; Engel, J. C.; McKerrow, J. H.; Craik, C. S.; Fletterick, R. J. J. Mol. Biol. 1995, 247, 251.
8. 8. Harth, G.; Andrews, N.; Mills, A. A.; Engel, J. C.; Smith, R.; McKerrow, J. H. Mol. Biochem. Parasitol. 1993, 58, 17.
9. 9. Serveau, C.; Lalmanach, G.; Juliano, M. A.; Scharfstein, J.; Juliano, L.; Gauthier, F. Biochem. J. 1996, 313, 951.
10. 10. Rasnick, D. In Cysteine Proteases: Evolution, Function and Inhibitor Design; McKerrow, J. H., James, M. N. G., Eds.; ESCOM Science Publishers: Leiden, 1996; Vol. 6; p 47.
11. 11. Rich, D. H. In Comprehensive Medicinal Chemistry; Sammes, P. G., Ed.; Pergamon Press: Oxford, 1990; Vol. 2; p 391.
12. 12. Hanada, K.; Tamai, M.; Ohmura, S.; Sawada, J.; Seki, T.; Tanaka, I. Agric. Biol. Chem. 1978, 42, 529.
13. 13. Tamai, M.; Hanada, K.; Adachi, T.; Oguma, K.; Kashiwagi, K.; Omura, S.; Ohzeki, M. J. Biochem. 1981, 90, 255.
14. 14. Varughese, K. I.; Ahmed, F. R.; Carey, P. R.; Hasnain, S.; Huber, C. P.; Storer, A. C. Biochemistry 1989, 28, 1330.
15. 15. Yamamoto, D.; Matsumoto, K.; Ohishi, H.; Ishida, T.; Inoue, M.; Kitamura, K.; Mizuno, H. J. Biol. Chem. 1991, 266, 14771.
16. 16. Kim, M.-J.; Yamamoto, D.; Matsumoto, K.; Inoue, M.; Ishida, T.; Mizuno, H.; Sumiya, S.; Kitamura, K. Biochem. J. 1992, 287, 797.
17. 17. Gillmor, S. A.; Craik, C. S.; Fletterick, R. J. Protein Sci. 1997, 6, 1603.
18. 18. Drenth, J.; Kalk, K. H.; Swen, H. M. Biochemistry 1976, 15, 3731.
19. 19. Krantz, A.; Copp, L. J.; Coles, P. J.; Smith, R. A.; Heard, S. B. Biochemistry 1991, 30, 4678.
20. 20. Spaltenstein, A.; Leban, J. J.; Huang, J. J.; Reinhardt, K. R.; Viveros, H.; Sigafoos, J.; Crouch, R. Tetrahedron Lett. 1996, 37, 1343.
21. 21. Naturally ocurring dipeptidyl epoxyketones have also been reported: Tsuchiya, K.; Kobayashi, S.; Nishikiori, T.; Nakagawa, T.; Tatsuta, K. J. Antibiot. 1997, 50, 261, and references therein.
22. 22. Giordano, C.; Gallina, C.; Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1990, 25, 479.
23. 23. Kim, D. H.; Kim, K. B. J. Am. Chem. Soc. 1991, 113, 3200.
24. 24. Albeck, A.; Fluss, S.; Persky, R. J. Am. Chem. Soc. 1996, 118, 3591.
25. 25. α-Amino aldehydes were synthesized from the corresponding methyl esters by DIBAL reduction (-78 °C) and Swern oxidation of the resulting alcohols, and were used immediately without purification.
26. 26. Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. Chem. Pharm. Bull. 1989, 37, 2867.
27. 27. Bodanszky, M. Principles of Peptide Synthesis; Verlag: New York, NY, 1993, pp 9-61.
28. 28. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
29. 29. Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 49, 4733.
30. 30. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
31. 31. Walker, M. A.; Heathcock, C. H. J. Org. Chem. 1991, 56, 5747.
32. 32. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
33. 33. Ninomiya, K.; Shiori, T.; Yamada, S. Tetrahedron 1974, 30, 2151.
34. 34. Beith, J. G. Methods in Enzymology 1995, 248, 59.
35. 33
36. 2Ph ("Mu" = morpholine urea), Arris Pharmaceuticals Inc., South San Francisco, CA (Palmer, J. T.; Rasnick, D.; Klaus, J. L.; Brömme, D. J. Med Chem. 1995, 38, 3193, and Brömme, D.; Klaus, J. L.; Okamoto, K.; Rasnick, D.; Palmer, J. T. Biochem. J. 1996, 315, 85)] were run with each assay set.
37. 2Ph ("Mu" = morpholine urea), Arris Pharmaceuticals Inc., South San Francisco, CA (Palmer, J. T.; Rasnick, D.; Klaus, J. L.; Brömme, D. J. Med Chem. 1995, 38, 3193, and Brömme, D.; Klaus, J. L.; Okamoto, K.; Rasnick, D.; Palmer, J. T. Biochem. J. 1996, 315, 85)] were run with each assay set.
38. 37. Kling, J.; M. S. Thesis, Indiana University, 1996.