Potent inhibition of influenza sialidase by a benzoic acid containing a 2-pyrrolidinone substituent

Journal of Medicinal Chemistry

Volumn 42, Issue 13, 1999, Pages 2332-2343

  Atigadda, Venkatram R ^a   Brouillette, Wayne J ^a   Duarte, Franco ^a   Ali, Shoukath M ^a   Babu, Yarlagadda S ^b   Bantia, Shanta ^b   Chand, Pooran ^b   Chu, Naiming ^b   Montgomery, John A ^b   Walsh, David A ^b   Sudbeck, Elise A ^a   Finley, James ^a   Luo, Ming ^a   Air, Gillian M ^c   Laver, Graeme W ^d  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

^b BIOCRYST PHARMACEUTICALS INC   (United States)

^c UNIVERSITY OF OKLAHOMA COLLEGE OF MEDICINE   (United States)

^d Biology and Environment   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 CARBOXY 2 GUANIDINOPHENYL) 5 (HYDROXYMETHYL)PYRROLIDIN 2 ONE; 1 (4 CARBOXY 2 GUANIDINOPHENYL) 5,5 BIS(HYDROXYMETHYL)PYRROLIDIN 2 ONE; 1 (4 CARBOXY 2 GUANIDINOPHENYL)PYRROLIDIN 2 ONE; 1 [4 CARBOXY 2 (3 PENTYLAMINO)PHENYL] 5,5 BIS(HYDROXYMETHYL)PYRROLIDIN 2 ONE; 4 (N ACETYLAMINO) 3 GUANIDINOBENZOIC ACID; 4 ACETAMIDO 3 GUANIDINOBENZOIC ACID; ANTIVIRUS AGENT; BENZOIC ACID DERIVATIVE; SIALIDASE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS ENZYME;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; HYDROPHOBICITY; INFLUENZA; INFLUENZA VIRUS A; INFLUENZA VIRUS B; NONHUMAN; SPECTROFLUOROMETRY; X RAY CRYSTALLOGRAPHY;

BENZOIC ACIDS; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; INFLUENZA A VIRUS; INFLUENZA B VIRUS; MODELS, MOLECULAR; NEURAMINIDASE; PYRROLIDINONES; SPECTROMETRY, FLUORESCENCE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033168078     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980707k     Document Type: Article

References (34)

1. (a) Air, G. M.; Laver, W. G. The Neuraminidase of Influenza Virus. Proteins: Struct., Funct., Genet. 1989, 6, 341-356.
2. (b) Ghate, A. N.; Air, G. M. Site-Directed Mutagenesis of Catalytic Residues of Influenza Virus Neuraminidase as an Aid to Drug Design. Eur. J. Biochem. 1998, 258, 320-331.
3. Palese, P.; Jobita, K.; Ueda, M.; Compans, E. W. Characterization of Temperature-Sensitive Influenza Virus Mutants Defective in Neuraminidase. Virology 1974, 61, 397-410.
4. Lin, C.; Eichelberger, M. C.; Compans, R. W.; Air, G. M. Influenza Type A Virus Neuraminidase Does Not Play a Role in Viral Entry, Replication, Assembly, or Budding. J. Virol. 1995, 69, 1099-1106.
5. Von Itzstein, M.; Wu, Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Van Phan, T.; Synthe, M. L.; White, H. F.; Oliver, S. W.; Coleman, P. G.; Varghese, V. J.; Cameron, J. M.; Penn, C. R. Rational Design of Potent Sialidase-Based Inhibitors of Influenza Virus Replication. Nature 1993, 363, 418-423.
6. (a) Burmeister, W. P.; Ruigrok, R. W. H.; Cusack, S. The 2.2 Å Resolution Crystal Structure of Influenza B Neuraminidase and its Complex with Sialic Acid. EMBO J. 1992, 11, 49-56.
7. (b) 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 A Resolution: Implication for the Catalytic Mechanism. Biochemistry 1994, 33, 8172-8179.
8. (c) Varghese, J. N.; Mckimm-Breschkin, J. L.; Caldwell, J. B.; Kortt, A. A.; Colman, P. M. The Structure of the Complex Between Influenza Virus Neuraminidase and Sialic Acid, the Viral Receptor. Proteins: Struct., Funct., Genet. 1992, 14, 327-332.
9. (d) Bossart-Whitaker, P.; Carson, M.; Babu, Y. S.; Smith, C. D.; Laver, W. G.; Air, G. M. Three-Dimensional Structure of Influenza A N9 Neuraminidase and its Complex with the Inhibitor 2-Deoxy-2,3-dehydro-N-acetyl Neuraminic Acid. J. Mol. Biol. 1993, 232, 1069-1083.
10. (e) Tulip, W. R.; Varghese, J. N.; Laver, W. G.; Colman, P. M. Refined Crystal Structure of the Influenza Virus N9 Neuraminidase-NC41 Fab Complex. J. Mol. Biol. 1992, 227, 122-148.
11. (f) Varghese, J. N.; Epa, V. C.; Colman, P. M. Three-dimensional Structure of the Complex of 4-Guanidino-Neu5Ac2en and Influenza Virus Neuraminidase. Protein. Sci. 1995, 4, 1081-1084.
12. (a) Colman, P. M.; Varghese, J. N.; Laver, W. G. Structure of the Catalytic and Antigenic Sites in Influenza Virus Neuraminidase. Nature (London) 1983, 303, 41-44.
13. (b) Air, G.; Laver, W. G.; Luo, M.; Stray, S. J.; Legrone, G.; Webster, R. G. Antigenic, Sequence, and Crystal Variation in Influenza B Neuraminidase. Virology 1990, 177, 578-587.
14. Meindl, P.; Bodo, G.; Palese, P.; Schulman, J.; Tuppy, H. Inhibition of Neuraminidase Activity by Derivatives of 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid. Virology 1975, 58, 457-463.
15. Holzer, C. T.; Von Itzstein, M.; Jin, B.; Pegg, M. S.; Stewart, W. P.; Wu, W.-Y. Inhibition of Sialidases from Viral, Bacterial and Mammalian Sources by Analogues of 2-Deoxy-2,3-didehydro-N-acetylneuraminic Acid Modified at the C-4 Position. Glycoconjugate J. 1993, 10, 40-44.
16. 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.
17. Hayden, F. G.; Treanor, J. J.; Betts, R. F.; Lobo, M.; Esinhart, J. D.; Hussey, E. K. Safety and Efficacy of the Neuraminidase Inhibitor GG 167 in Experimental Human Influenza. J. Am. Med. Assoc. 1996, 275, 295-299.
18. Ryan, D. M.; Ticeburst, J.; Dempsey, M. H.; Penn, C. R. Inhibition of Influenza Virus Replication in Mice by GG 167 is Consistent with Extracellular Activity of Viral Neuraminidase. Antimicrob. Agents Chemother. 1994, 38, 2270-2275.
19. Sollis, S. L.; Smith, P. W.; Howes, P. D.; Cherry, P. C.; Bethell, R. C. Novel Inhibitors of Influenza Sialidase Related to GG 167. Synthesis of 4-Amino and Guanidino-4H-pyran-2-carboxylic Acid-6-propylamides; Selective Inhibitors of Influenza A Virus Salidase. Bioorg. Med. Chem. Lett. 1996, 6, 1805-1808.
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.; Varghese, J.; Colman, P.; Singh, O.; Skarzynski, T.; Cleasby, A.; Woncott, A. Novel Ihibitors of Ifluenza Salidase Rlated to GG 167. Structure-Activity, Crystallographic and Molecular Dynamics Studies with 4H-Pran-2-carboxylic Acid 6-Carboxamides. Bioorg. Med. Chem. Lett. 1996, 24, 2931-2936.
21. Kim, C. V.; 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.
22. Jedrzejas, M. J.; Singh, S.; Brouillette, W. J.; Laver, G. W.; Air, G. M.; Luo, M. Structures of Aromatic Inhibitors of Influenza Virus Neuraminidase. Biochemistry 1995, 34, 3144-3151.
23. Singh, S.; Jedrzejas, M. J.; Air, G. M.; Luo, M.; Laver, W. G.; Brouillette, W. J. Structure-Based Inhibitors of Influenza Virus Sialidase. A Benzoic Acid Lead with Novel Interaction. J. Med. Chem. 1995, 38, 3217-3225.
24. Sudbeck, E. A.; Jedrzejas, M. J.; Singh, S.; Brouillette, W. J.; Air, G. M.; Laver, W. G.; Babu, Y. S.; Bantia, S.; Chand, P.; Chu, N.; Montgomery, J. A.; Walsh, D. A.; Luo, M. Guanidinobenzoic Acid Inhibitors of Influenza Virus Neuraminidase. J. Mol. Biol. 1997, 267, 584-594.
25. Williams, M.; Bischofberger, N.; Swaminathan, S.; Kim, C. U. Synthesis And Influenza Neuraminidase Activity of Aromatic Analogues of Sialic Acid. Bioorg. Med. Chem. Lett. 1995, 5, 2251-2254.
26. Kim, K. S.; Qian, L. Improved Method for the Preparation of Guanidines. Tetrahedron Lett. 1993, 34, 7677-7680.
27. Chatterjee, B. G.; Rao, V. V.; Majumdar, B. N. G. Synthesis of Substituted β- and γ-Lactams. J. Org. Chem. 1965, 30, 4101-4104.
28. Barney, C. L.; Huber, E. W.; Macarthy, J. R. A Convenient Synthesis of Hindered Amines And a-Trifluoromethyamines from Ketones. Tetrahedron Lett. 1990, 31, 5547-5550.
29. von Itzstein, L. M.; Wu, W.-Y.; Phen, T. V.; Betty, J. Antiviral 4-Subatituted-2-deoxy-2,3-didehydro Derivatives of α-D-Neuraminic Acid. EP Application 92309684.6, 1993.
30. Laver, W. G.; Coleman, P. M.; Webster, R. G.; Hinshaw, V. S.; Air, G. M. Influenza Virus Neuraminidase with Hemagglutinin Activity. Virology 1984, 137, 314-323.
31. Smith, P. W.; Sollis, S. L.; Howes, P. D.; Starkey, I. D.; Cobley, K. N.; Weston, H.; Scicinski, J.; Merritt, A.; Whittington, W. P.; Taylor, N.; Green, D.; Bethell, R.; Madar, S.; Fenton, R. J.; Morley, P. J.; Pateman, T.; Beresford, A. Dihydropyrancarboxamides Related to Zanamavir: A New Series of Inhibitors of Influenza Virus Sialidases. 1. Discovery, Synthesis, Biological Activity, and Structure-Activity Relationships of 4-Guanidino- and 4-Amino-4H-pyran-6-carboxamides. J. Med. Chem. 1998, 41, 787-797.
32. Taylor, N. R.; Cleasby, A.; Singh, O.; Skarzynski, T.; Wonacott, A. J.; Smith, P. A.; Sollis, S. L.; Howes, P. C.; Bethell, R.; Colaman, P.; Varghese, J. Dihydropyrancarboxamides Related to Zanamavir: A New Series of Inhibitors of Influenza Virus Sialidases. 2. Crystallographic and Molecular Modeling Study of Complexes of 4-Amino-4H-pyran-6-carboxamides and Sialidase from Influenza Virus Types A and B. J. Med. Chem. 1998, 41, 798-807.
33. Kim, C. U.; Lew, W.; Williams, M. A.; Wu, H.; Zhang, L.; Chem, X.; Excarpe, P. A.; Mendel, D. B.; Laver, W. G.; Stevens, R. C. Structure-Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors. J. Med. Chem. 1998, 41, 2451-2460.
34. Brouillette, W. J.; Atigadda, V. R.; Luo, M.; Air, G. M.; Babu, Y. S.; Bantia, S. Design of Benzoic Acid Inhibitors of Influenza Neuraminidase Containing a Cyclic Substitution for the N-Acetyl Grouping. Bioorg. Med. Chem. Lett. 1999, in press.