Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors

Journal of Medicinal Chemistry

Volumn 41, Issue 14, 1998, Pages 2451-2460

  Kim, Choung U ^a   Lew, Willard ^a   Williams, Matthew A ^a   Wu, Huiwei ^a   Zhang, Lijun ^a   Chen, Xiaowu ^a   Escarpe, Paul A ^a   Mendel, Dirk B ^a   Laver, W Graeme ^b   Stevens, Raymond C ^c  

^a GILEAD SCIENCES   (United States)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; 4 ACETAMIDO 5 AMINO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLIC ACID; ETHYL 4 ACETAMIDO 5 AZIDO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLATE PHOSPHATE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS ENZYME; ZANAMIVIR;

AMINO ACID SEQUENCE; ARTICLE; DRUG EFFICACY; ENANTIOMER; ENZYME INHIBITION; ENZYME STRUCTURE; HUMAN; HYDROPHOBICITY; INFLUENZA; INFLUENZA VIRUS A; LIPOPHILICITY; ORAL DRUG ADMINISTRATION; PROPHYLAXIS; STRUCTURE ACTIVITY RELATION; VIRUS INFECTION; X RAY CRYSTALLOGRAPHY;

ACETAMIDES; ANTIVIRAL AGENTS; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; INFLUENZA A VIRUS; INFLUENZA B VIRUS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEURAMINIDASE; OSELTAMIVIR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 15444353753     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980162u     Document Type: Article

References (28)

1. Colman, P. M. In The Influenza Viruses: Influenza Virus Neuraminidase, Enzyme and Antigen; Krug, R. M., Ed.; Plenum Press: New York, 1989; pp 175-218.
2. Colman, P. M. Influenza Virus Neuraminidase: Structure, Antibodies and Inhibitors. Protein Sci. 1994, 3, 1687-1696.
3. Palese, P.; Tobita, K.; Ueda, M.; Compans, R. W. Characterization of Temperature Sensitive Influenza Virus Mutants Defective in Neuraminidase. Virology 1974, 61, 397-410.
4. Liu, C.; Air, G. M. Selection and Characterization of a Neuraminidase-Minus Mutant of Influenza Virus and its Rescue by Cloned Neuraminidase Genes. Virology 1993, 193, 1-5.
5. Janakiraman, M. N.; White, C. L.; Laver, W. G.; Air, G. M.; Luo, M. Structure of Influenza Virus Neuraminidase B/Lee/40 Complexed with Sialic Acid and a Dehydro Analogue at 1.8-Å Resolution: Implication for the Catalytic Mechanism. Biochemistry 1994, 33, 8172-8179.
6. Chong, A. K. J.; Pegg, M. S.; Taylor, N. R.; Von Itzstein, M. Evidence for a Sialosyl Cation Transition-State Complex in the Reaction of Sialidase from Influenza Virus. Eur. J. Biochem. 1992, 207, 335-343.
7. Taylor, N. R.; Von Itzstein, M. Molecular Modeling Studies on Ligand Binding to Sialidase from Influenza Virus and the Mechanism of Catalysis. J. Med. Chem. 1994, 37, 616-624.
8. Von Itzstein, M.; Wu, W.-Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smyth, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryan, D. M.; Woud, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M.; Penn, C. R. Rational Design of Potent Sialidase-Based Inhibitors of Influenza Virus Replication. Nature (London) 1993, 303, 418-423.
9. Fromtling, R. A.; Castaner, J. Zanamivir. Drugs Future 1996, 21, 375-382.
10. Hayden, F. G.; Osterhaus, J. J.; Treanor, D. M.; Fleming, F. Y.; Aoki, K. G.; Nicholson, A. M.; Bohnen, H. M.; Hirst, H. M.; Keene, O.; Wightman, K. Efficacy and Safety of the Neuraminidase Inhibitor Zanamivir in the Treatment of Influenza Virus Infections. N. Engl. J. Med. 1997, 337, 874-880.
11. Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. Influenza Neuraminidase Inhibitors Possessing a Novel Hydrophobic Interaction in the Enzyme Active Site: Design, Synthesis and Structural Analysis of Carbocyclic Sialic Acid Analogues with Potent Anti-Influenza Activity. J. Am. Chem. Soc. 1997, 119, 681-690.
12. Mendel, D. B.; Tai, C. Y.; Escarpe, P. A.; Li, W.; Sidwell, R. W.; Huffman, J. H.; Sweet, C.; Jakeman, K. J.; Merson, J.; Lacy, S. A.; Lew, W.; Williams, M. A.; Zhang, L.; Chen, M. S.; Bischofberger, N.; Kim, C. U. Oral Administration of a Prodrug of the Influenza Neuraminidase Inhibitor GS 4071 Protects Mice and Ferrets Against Influenza Infection. Antimicrob. Agents Chemother. 1998, 42, 640-646.
13. Hayden, F. G.; Lobo, M.; Treanor, J. J.; Miller, M.; Mills, R. G. Efficacy and Tolerability of Oral GS 4104 for Early Treatment of Experimental Influenza in Humans. 37th ICAAC, Late Breaker Session, Toronto, Ontario, Canada, September, 1997.
14. Klunder, J. M.; Onami, T.; Sharpless, K. B.; Arenesulfonate Derivatives of Homo Chiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis. J. Org. Chem. 1989, 54, 1295-1304.
15. Kim, K. S.; Qian, L. Improved Method for the Preparation of Guanidines. Tetrahedron Lett. 1993, 34, 7677-7680.
16. Rich, R. H.; Bartlett, P. A. Synthesis of (-)-2-Fluoroshikimic Acid. J. Org. Chem. 1996, 61, 3916-3919.
17. Williams, M. A.; Lew, W.; Mendel, D. B.; Tai, C. Y.; Escarpe, P. A.; Laver, W. G.; Stevens, R. C.; Kim, C. U. Structure-Activity Relationships of Carbocyclic Influenza Neuraminidase Inhibitors. Bioorg. Med. Chem. Lett. 1997, 7, 1837-1842.
18. Belpaire, F. M.; Bogaert, M. G. In The Practice of Medicinal Chemistry: The Fate of Xenobiotics in Living Organisms; Wermuth, C. G., Ed.; Academic Press: New York, 1996; pp 596-600.
19. Hummer, G.; Garde, S.; Garcia, A. E.; Pohorille, A.; Pratt, L. R. An Information Theory Model of Hydrophobic Interactions. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8951-8955.
20. Smith, P. W.; Sollis, S. L.; Howes, P. D.; Cherry, P. C.; Cobley, K. N.; Taylor, H.; Whittington, A. R.; Scicinski, J.; Bethell, R. C.; Taylor, N.; Skarzynski, T.; Clersby, A.; Singh, O.; Wonacott, A.; Varghese, J.; Colman, P. Novel Inhibitors of Influenza Sialidases Related to GG167. Bioorg. Med. Chem. Lett. 1997, 7, 1837-1842.
21. Filler, R.; Naqvi, S. M. In Biomedicinal Aspects of Fluorine Chemistry; Filler, R.; Kobayashi, Y., Ed.; Elsevier Biochemical: Amsterdam, New York, Oxford, 1982; pp 1-32.
22. Potier, M.; Mameli, L.; Belisle, M.; Dallaire, L.; Melancon, S. B. Fluorometric Assay of Neuraminidase With a Sodium (4-methylumbelliferyl-α-D-N-acetylneuraminate) Substrate. Anal. Biochem. 1979, 94, 287-296.
23. Laver, W. G.; Colman, P. M.; Webster, R. G.; Hinshaw, V. S.; Air, G. M.; Influenza Virus Neuraminidase with Hemagglutinin Activity. Virology 1984, 137(2), 314-323.
24. White, C. L.; Janakiraman, M. N.; Laver, W. G.; Philippon, C.; Vasella, A.; Air, G. M.; Luo, M. A Sialic Acid-Derived Phosphonate Analogue Inhibits Different Strains of Influenza Virus Neuraminidase with Different Efficiencies. J. Mol. Biol. 1995, 245, 623-634.
25. Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Improved Methods for Building Protein Models in Electron Density Maps and the Location of Errors in These Models. Acta Crystallogr., Sect. A: Found. Crystallogr. 1991, A47, 110-119.
26. Brunger, A. T. The X-PLDR 3.1 Software; Yale University: New Haven, CT, 1993.
27. Biosym Technologies, 1992.
28. Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thornton, J. M. PROCHECK: A Program to Check the Stereochemical Quality of Protein Structures. J. Appl. Crystallogr. 1993, 26, 283-291.