Synthesis and testing of azaglutamine derivatives as inhibitors of Hepatitis A Virus (HAV) 3C proteinase

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 4, 1999, Pages 607-619

  Huang, Yanting ^a   Malcolm, Bruce A ^b   Vederas, John C ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b TUFTS UNIVERSITY   (United States)

Author keywords

Antiviral agents; Azapeptides; Cysteine proteinase; Enzyme inhibitors

Indexed keywords

CYSTEINE PROTEINASE INHIBITOR; GLUTAMINE DERIVATIVE; SULFONAMIDE;

CONFERENCE PAPER; DRUG DESIGN; DRUG SYNTHESIS; ENZYME INHIBITION; HEPATITIS A VIRUS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

CYSTEINE ENDOPEPTIDASES; GLUTAMINE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PROTEASE INHIBITORS; VIRAL PROTEINS;

HEPATITIS A VIRUS;

EID: 0032986993     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00006-1     Document Type: Conference Paper

References (45)

1. (a) Bergmann, E. M.; James, M. N. G. In Proteinases of Infectious Agents, Dunn, B., Ed.; Academic Press: San Diego, CA, 1998, in press.
2. (b) Gorbalenya, A. E; Snijder, E. J. Perspectives in Drug Discovery and Design 1996, 6, 64-86.
3. Rueckert, R. R. In Fields Virology; Fields, B. N.; Knipe, D. M.; Howley, P. M.; Channock, R. M.; Melnick, J. L.; Monath, T. P.; Roizmann, B.; Straus, S. E., Eds.; Lippincott-Raven Publishers: Philadelphia, PA, 1997.
4. Ryan, M. D.; Flint, M. J. Gen. Virol. 1997, 78, 699-723.
5. (a) Krausslich, H. G.; Wimmer, E. Annu. Rev. Biochem. 1988, 57, 701-754.
6. (b) Rasnick, D. Perspectives in Drug Discovery and Design 1996, 6, 47-63.
7. Malcolm, B. A. Protein Sci. 1995, 4, 1439-1445.
8. Allaire, M.; Chernaia, M. M.; Malcolm, B. A.; James, M. N. G. Nature 1994, 369, 72-76.
9. Bergmann, E. M.; Mosimann, S. C.; Chernaia, M. M.; Malcolm, B. A.; James, M. N. G. J. Virol. 1997, 71, 2436-2448.
10. Matthews, D. A.; Smith, W. W.; Ferre, R. A.; Condon, B.; Budahazi, G.; Sisson, W.; Villafranca, J. E.; Janson, C. A.; McElroy, H. E.; Gribskov, C. L.; Worland, S. Cell 1994, 77, 761-771.
11. Mosimann, S. C.; Cherney, M. M.; Sia, S.; Plotch, S.; James, M. N. G. J. Mol. Biol. 1997, 273, 1032-1047.
12. Ng, L. F. P.; Liu, D. X. Virology, 1998, 243, 388-395.
13. Ziebuhr, L; Heusipp, G.; Siddell, S. G. J. Virology 1997; 71, 3992-3997.
14. Dragovich, P. S.; Webber, S. E.; Babine; R. E.; Fuhrman; S. A.; Patick; A. K.; Matthews; D. A.; Lee, C. A.; Reich, S. H.; Prins; T. L.; Marakovits, J. T.; Littlefield, E. S.; Zhou, R.; Tikhe, L.; Ford, C. E.; Wallace, M. B.; Meador, J. W. III; Ferre, R. A.; Brown, E. L.; Binford, S. L.; Harr, J. E. V.; DeLisle, D. M.; Worland, S. T. J. Med. Chem. 1998, 41, 2806-2818, and references therein.
15. Malcolm, B. A.; Lowe, C.; Shechosky, S.; McKay, R. T.; Yang, C. C.; Shah, V. L.; Simon, R. L.; Vederas, J. C. and Santi, D. V. Biochemistry 1995, 34, 8172-8179.
16. Kaldor, S. W.; Hammond, M.; Dressman, B. A.; Labus, J. M.; Chadwell, F. W.; Kline, A. D.; Heirnz, B. A. Bioorg. Med. Chem. Lett. 1995, 5, 2021-2026.
17. Shepherd, T. A.; Cox, G. A.; McKinney, E.; Tang, L.; Wakulchik, M.; Zimmerman, R. E.; Villarreal, E. C. Bioorg. Med. Chem. Lett. 1996, 6, 2893-2896.
18. Morris, T. S.; Frormann, S.; Shechosky, S.; Lowe, C.; Lall, M. S.; Gauss-Müller, V.; Plurcell, R. H.; Emerson, S. U.; Vederas, J. C.; Malcolm, B. A. Bioorg. Med. Chem. 1997, 5, 797-807.
19. Skiles, J. W.; McNeil, D. Tetrahedron 1990, 31, 7277-7280.
20. Webber, S. E.; Tikhe, J.; Worland, S. T.; Fuhrman, S. A.; Hendrickson, T. R.; Matthews, D. A.; Love, R. A.; Patick, A. K.; Meador, J. W.; Ferre, R. A.; Brown, E. L.; DeLisle, D. M.; Ford, C. E.; Binford, S. L. J. Med. Chem. 1996, 39, 5072-5082.
21. Jungheim, L. N.; Cohen, J. D.; Johnson, R. B.; Villarreal, E. C.; Wakulchik, M.; Loncharich, R. L.; Wang, Q. M. Bioorg. Med. Chem. Lett. 1997, 7, 1589-1594.
22. Kong, J.; Venkatraman, S.; Furness, K.; Nimkar, S.; Shepherd, T. A.; Wang, Q. M.; Aubé, J.; Hanzlik, R. P. J. Med. Chem. 1998, 41, 2579-2587.
23. Dragovich, P. S.; Webber, S. E.; Babine; R. E.; Fuhrman; S. A.; Patick,; A. K.; Matthews,; D. A.; Reich, S. H.; Marakovits, J. T.; Prins; T. J.; Zhou, R.; Tikhe, J.; Littlefield, E. S.; Bleckman, T. M.; Wallace, M. B.; Little, T. L.; Ford, C. E.; Meador, J. W. III; Ferre, R. A.; Brown, E. L.; Binford, S. L.; DeLisle, D. M.; Worland, S. T. J. Med. Chem. 1998, 41, 2819-2834.
24. Sham, H. L.; Rosenbrook, W.; Kati, W.; Betebenner, D. A.; Wideburg, N. E.; Saldivar, A.; Plattner, J. J.; Norbeck, D. W. J. Chem. Soc., Perkin Trans. 1 1995, 1081-1082.
25. McKendrick, J. E.; Frormann, S.; Luo, C.; Semchuck, P.; Vederas, J. C.; Malcolm, B. A. Int. J. Mass. Spectrom. 1998, in press.
26. For discussion and leading references to azapeptides see: Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 2539-2544.
27. For an example of an orally-available azapeptide inhibitor of HIV-1 protease see: Fässler, A.; Bold, G.; Capraro, H.-G.; Cozens, R.; Mestan, J.; Poncioni, B.; Rösel, J.; Tintelnot-Blomley, M.; Lang, M. J. Med. Chem. 1996, 39, 3203-3216.
28. Abeles; R. H.; Magrath, J. J. Med. Chem. 1992, 35, 4279-4283.
29. Xing, R.; Hanzlik, R. P. J. Med. Chem. 1998, 41, 1344-1351.
30. Thompson, S. K.; Halbert, S. M.; Bossard, M. J.; Tornaszek, T. A.; Levy, M. A.; Zhao, B.; Smith, W. W.; Abdel-Meguid, S. S.; Janson, C. A.; D'Alessio, K. J.; McQueney, M. S.; Amegadzie, B. Y.; Hanning, C. R.; DesJarlais, R. L.; Briand, J.; Sarkar, S. K.; Huddleston, M. J.; Ijames, C. F.; Carr, S. A.; Garnes, K. T.; Shu, A.; Heys, J. R.; Bradbeer, J.; Zembryki, D.; Lee-Rykaczewski, L.; James, I. E.; Lark, M. W.; Drake, F. K.; Gowen, M.; Gleason, J. G.; Veber, D. F. Proc. Natl. Acad. Sci. 1997, 94, 14249-14254.
31. For related work using amino ketones see: Yamashita, D. S.; Smith, W. W.; Zhao, B.; Janson, C. A.; Tomaszek, T. A.; Bossard, M. J.; Levy, M. A.; Oh, H. J.; Carr, T. J.; Thompson, S. K.; Ijames, C. F.; Carr, S. A.; McQueney, M.; D'Alessio, K. L.; 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.
32. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991; pp 377-378.
33. Kice, J. L.; Kutateladze, A. G. J. Org. Chem. 1992, 57, 3298-3303.
34. Pu, Y.; Lowe, C.; Sailer, M.; Vederas, J. C. J. Org. Chem. 1994, 59, 3642-3655.
35. A preliminary portion of this work has been mentioned in a recent review but without experimental detail: Frormann, S.; Huang, Y.; Lall, M.; Lowe, C.; Vederas, J. C. In Recent Advances in the Chemistry of Anti-Infective Agents, Bentley, P. H.; O'Hanlon, P. J.; Eds., Royal Society of Chemistry: Cambridge, UK, 1997: pp 298-315.
36. Wood, J. L.; Jeong, S.; Salcedo, A.; Jenkins, J. J. Org. Chem. 1995, 60, 286-287.
37. Albeck, A.; Persky, R. Tetrahedron 1994, 50, 6333-6346.
38. Jones, C. D. J. Org. Chem. 1972, 37, 3624-3625.
39. Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 1054-1062.
40. Jewell, D. A.; Swietnicki, W.; Dunn, B. M.; Malcolm, B. A. Biochemistry 1992, 31, 7862-7869.
41. Malcolm, B. A.; Chin, S. M.; Jewell, D. A.; Stratton-Thomas, J. R.; Thudium, K. B.; Ralston, R.; Rosenberg, S. Biochemistry 1992, 31, 3358-3363.
42. 2, has been solved by Michael N. James and Ernst M. Bergmann (Biochemistry Department, University of Alberta). Details of the crystallization methodology and solution of the crystal structure will be reported elsewhere.
43. Witter, D. J.; Vederas, J. C. J. Org. Chem. 1996, 61, 2613-2623.
44. Lettieri, G.; Brancaccio, G.; Larizza, A. Boll. Chim. Farm. 1981, 12, 308-310.
45. Molander, G. A.; Stengel, P. J. Tetrahedron 1997, 53, 8887-8912.