Serendipitous discovery of a potent influenza virus A neuraminidase inhibitor

Angewandte Chemie - International Edition

Volumn 53, Issue 4, 2014, Pages 1076-1080

  Mohan, Sankar ^a   Kerry, Philip S ^b   Bance, Nicole ^a   Niikura, Masahiro ^a   Pinto, B Mario ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

^b UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

antiviral agents; drug discovery; influenza A; neuraminidase inhibitors; spiro compounds

Indexed keywords

DRUG DISCOVERY; INFLUENZA A; INHIBITORY ACTIVITY; LEAD OPTIMIZATION; NEURAMINIDASE INHIBITORS; SERENDIPITOUS DISCOVERY; SPIRO COMPOUNDS; X RAY CRYSTAL STRUCTURES;

ANTIVIRAL AGENTS; VIRUSES;

CELL CULTURE;

ANTIVIRUS AGENT; ENZYME INHIBITOR; LACTAM; NA PROTEIN, INFLUENZA A VIRUS; SIALIDASE; SPIRO COMPOUND; VIRUS PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG ANTAGONISM; DRUG DEVELOPMENT; INFLUENZA A; METABOLISM; NEURAMINIDASE INHIBITORS; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTIVIRAL AGENTS; DRUG DISCOVERY; INFLUENZA A; NEURAMINIDASE INHIBITORS; SPIRO COMPOUNDS;

CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; ENZYME INHIBITORS; LACTAMS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEURAMINIDASE; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL PROTEINS;

EID: 84893334934     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308142     Document Type: Article

References (31)

1. World Health Organization. Influenza at the human-animal interface. 29th August 2013 (accessed November 2013).
2. C. U. Kim et al., J. Am. Chem. Soc. 1997, 119, 681-690. For complete citation, see the Supporting Information.
3. N. R. Taylor, M. von Itzstein, J. Med. Chem. 1994, 37, 616-624
4. M. von Itzstein, W. Y. Wu, B. Jin, Carbohydr. Res. 1994, 259, 301-305
5. M. von Itzstein et al., Nature 1993, 363, 418-423. For complete citation, see the Supporting Information.
6. Y. S. Babu et al., J. Med. Chem. 2000, 43, 3482-3486, for complete citation, see the Supporting Information
7. P. Chand, P. L. Kotian, A. Dehghani, Y. El-Kattan, T. H. Lin, T. L. Hutchison, Y. S. Babu, S. Bantia, A. J. Elliott, J. A. Montgomery, J. Med. Chem. 2001, 44, 4379-4392.
8. Q. Li, X. Sun, Z. Li, Y. Liu, C. J. Vavricka, J. Qi, G. F. Gao, Proc. Natl. Acad. Sci. USA 2012, 109, 18897-18902
9. X. Zhu, H. Yang, Z. Guo, W. Yu, P. J. Carney, Y. Li, L. M. Chen, J. C. Paulson, R. O. Donis, S. Tong, J. Stevens, I. A. Wilson, Proc. Natl. Acad. Sci. USA 2012, 109, 18903-18908.
10. R. J. Russell, L. F. Haire, D. J. Stevens, P. J. Collins, Y. P. Lin, G. M. Blackburn, A. J. Hay, S. J. Gamblin, J. J. Skehel, Nature 2006, 443, 45-49.
11. P. J. Collins, L. F. Haire, Y. P. Lin, J. Liu, R. J. Russell, P. A. Walker, J. J. Skehel, S. R. Martin, A. J. Hay, S. J. Gamblin, Nature 2008, 453, 1258-1261
12. P. J. Collins, L. F. Haire, Y. P. Lin, J. Liu, R. J. Russell, P. A. Walker, S. R. Martin, R. S. Daniels, V. Gregory, J. J. Skehel, S. J. Gamblin, A. J. Hay, Vaccine 2009, 27, 6317-6323
13. L. V. Gubareva, L. Kaiser, M. N. Matrosovich, Y. Soo-Hoo, F. G. Hayden, J. Infect. Dis. 2001, 183, 523-531
14. A. Lackenby, O. Hungnes, S. G. Dudman, A. Meijer, W. J. Paget, A. J. Hay, M. C. Zambon, Euro Surveill. 2008, 13(5).
15. J. L. McKimm-Breschkin, Influenza Other Respir. Viruses 2013, 7 (Suppl 1), 25- 36. DOI: 10.1111/irv.12047
16. L. V. Gubareva, Virus Res. 2004, 103, 199-203.
17. S. Mohan, S. McAtamney, T. Haselhorst, M. von Itzstein, B. M. Pinto, J. Med. Chem. 2010, 53, 7377-7391.
18. M. Niikura, N. Bance, S. Mohan, B. M. Pinto, Antiviral Res. 2011, 90, 160-163.
19. P. S. Kerry, S. Mohan, R. J. M. Russell, N. Bance, M. Niikura, B. M. Pinto, Sci. Rep. 2013, 3, 2871.
20. Y. Wu, F. Gao, J. Qi, S. Mohan, B. M. Pinto, C. J. Vavricka, G. F. Gao, unpublished results.
21. A. Albohy, S. Mohan, R. B. Zheng, B. M. Pinto, C. W. Cairo, Bioorg. Med. Chem. 2011, 19, 2817-2822.
22. K. Hata, K. Koseki, K. Yamaguchi, S. Moriya, Y. Suzuki, S. Yingsakmongkon, G. Hirai, M. Sodeoka, M. von Itzstein, T. Miyagi, Antimicrob. Agents Chemother. 2008, 52, 3484.
23. R. Wagner, M. Matrosovich, H. D. Klenk, Rev. Med. Virol. 2002, 12, 159-166.
24. E. Garman, G. Laver, in Viral Membrane Proteins: Structure, Function, and Drug Design (Ed.:, W. B. Fischer,), Kluwer Academic/Plenum Press, New York, 2005, pp. 247-267.
25. P. J. Steel, J. A. M. Guard, Acta Crystallogr. Sect. C 1994, 50, 1721-1723
26. M. M. Chowdhry, D. M. P. Mingos, A. J. P. White, D. J. Williams, J. Chem. Soc. Perkin Trans. 2 2000, 2265-2268.
27. R. E. Amaro, R. V. Swift, L. Votapka, W. W. Li, R. C. Walker, R. M. Bush, Nat. Commun. 2011, 2, 388.
28. S. Rudrawar, J. C. Dyason, M. A. Rameix-Welti, F. J. Rose, P. S. Kerry, R. J. Russell, S. van der Werf, R. J. Thomson, N. Naffakh, M. von Itzstein, Nat. Commun. 2010, 1, 113.
29. R. E. Amaro, X. L. Cheng, I. Ivanov, D. Xu, J. A. McCammon, J. Am. Chem. Soc. 2009, 131, 4702-4709
30. R. E. Amaro, D. D. L. Minh, L. S. Cheng, W. M. Lindstrom, A. J. Olson, J. H. Lin, W. W. Li, J. A. McCammon, J. Am. Chem. Soc. 2007, 129, 7764-7765
31. U. Grienke, M. Schmidtke, S. von Grafenstein, J. Kirchmair, K. R. Liedl, J. M. Rollinger, Nat. Prod. Rep. 2012, 29, 11-36.