Synthesis of C-4-modified zanamivir analogs as neuraminidase inhibitors and their anti-AIV activities

European Journal of Medicinal Chemistry

Volumn 54, Issue , 2012, Pages 764-770

  Ye, Deju ^a   Shin, Woo Jin ^b   Li, Ning ^a   Tang, Wei ^a   Feng, Enguang ^a   Li, Jian ^a   He, Pei Lan ^a   Zuo, Jian Ping ^a   Kim, Hanjo ^c   Nam, Ky Youb ^c   Zhu, Weiliang ^a   Seong, Baik Lin ^b   Tai No, Kyoung ^b   Jiang, Hualiang ^a   Liu, Hong ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b Yonsei University   (South Korea)

^c Bioinformatics and Molecular Design Research Center (BMDRC)   (South Korea)

Author keywords

Avian influenza virus (AIV); H5N1; Inhibitor; Neuraminidase (NA); Zanamivir

Indexed keywords

GUANIDINE; GUANIDINIUM BIOISOSTERE; SIALIDASE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; ZANAMIVIR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIVIRAL ACTIVITY; ARTICLE; AVIAN INFLUENZA; AVIAN INFLUENZA VIRUS; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; INFLUENZA VIRUS A H3N2; INFLUENZA VIRUS A H5N1; MALE; NONHUMAN; PLASMA HALF LIFE; RAT;

ANIMALS; ANTIVIRAL AGENTS; CHEMISTRY TECHNIQUES, SYNTHETIC; DOGS; ENZYME INHIBITORS; INFLUENZA A VIRUS, H3N2 SUBTYPE; INFLUENZA A VIRUS, H5N1 SUBTYPE; MADIN DARBY CANINE KIDNEY CELLS; MALE; NEURAMINIDASE; RATS; ZANAMIVIR;

EID: 84864402401     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.06.033     Document Type: Article

References (28)

1. W.H. Wen, M. Lin, C.Y. Su, S.Y. Wang, Y.S. Cheng, J.M. Fang, and C.H. Wong Synergistic effect of zanamivir-porphyrin conjugates on inhibition of neuraminidase and inactivation of influenza virus J. Med. Chem. 52 2009 4903 4910
2. J. Magano Synthetic approaches to the neuraminidase inhibitors zanamivir (Relenza) and oseltamivir phosphate (Tamiflu) for the treatment of influenza Chem. Rev. 109 2009 4398 4438
3. J. Zhang, and W. Xu Recent advances in anti-influenza agents with neuraminidase as target Mini. Rev. Med. Chem. 6 2006 429 448
4. A.J. Oakley, S. Barrett, T.S. Peat, J. Newman, V.A. Streltsov, L. Waddington, T. Saito, M. Tashiro, and J.L. McKimm-Breschkin Structural and functional basis of resistance to neuraminidase inhibitors of influenza B viruses J. Med. Chem. 53 2010 6421 6431
5. A.K. Weight, J. Haldar, L. Alvarez de Cienfuegos, L.V. Gubareva, T.M. Tumpey, J. Chen, and A.M. Klibanov Attaching zanamivir to a polymer markedly enhances its activity against drug-resistant strains of influenza a virus J. Pharm. Sci. 100 2011 831 835
6. I.M. Lagoja, and E. De Clercq Anti-influenza virus agents: synthesis and mode of action Med. Res. Rev. 28 2008 1 38 (Pubitemid 350274960)
7. M. von Itzstein The war against influenza: discovery and development of sialidase inhibitors Nat. Rev. Drug Discov. 6 2007 967 974
8. Z.Y. Liu, B. Wang, L.X. Zhao, Y.H. Li, H.Y. Shao, H. Yi, X.F. You, and Z.R. Li Synthesis and anti-influenza activities of carboxyl alkoxyalkyl esters of 4-guanidino-Neu5Ac2en (zanamivir) Bioorg. Med. Chem. Lett. 17 2007 4851 4854 (Pubitemid 47187697)
9. T. Honda, S. Kubo, T. Masuda, M. Arai, Y. Kobayashi, and M. Yamashita Synthesis and in vivo influenza virus-inhibitory effect of ester prodrug of 4-guanidino-7-O-methyl-Neu5Ac2en Bioorg. Med. Chem. Lett. 19 2009 2938 2940
10. 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, and S.J. Gamblin Crystal structures of oseltamivir-resistant influenza virus neuraminidase mutants Nature 453 2008 1258 1261 (Pubitemid 351913590)
11. R.J. Russell, L.F. Haire, D.J. Stevens, P.J. Collins, Y.P. Lin, G.M. Blackburn, A.J. Hay, S.J. Gamblin, and J.J. Skehel The structure of H5N1 avian influenza neuraminidase suggests new opportunities for drug design Nature 443 2006 45 49 (Pubitemid 44344043)
12. Y. Liu, F. Jing, Y. Xu, Y. Xie, F. Shi, H. Fang, M. Li, and W. Xu Design, synthesis and biological activity of thiazolidine-4-carboxylic acid derivatives as novel influenza neuraminidase inhibitors Bioorg. Med. Chem. 19 2011 2342 2348
13. J. An, D.C. Lee, A.H. Law, C.L. Yang, L.L. Poon, A.S. Lau, and S.J. Jones A novel small-molecule inhibitor of the avian influenza H5N1 virus determined through computational screening against the neuraminidase J. Med. Chem. 52 2009 2667 2672
14. W.H. Wen, S.Y. Wang, K.C. Tsai, Y.S. Cheng, A.S. Yang, J.M. Fang, and C.H. Wong Analogs of zanamivir with modified C4-substituents as the inhibitors against the group-1 neuraminidases of influenza viruses Bioorg. Med. Chem. 18 2010 4074 4084
15. 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, and M. von Itzstein Novel sialic acid derivatives lock open the 150-loop of an influenza A virus group-1 sialidase Nat. Commun. 1 2010 113 119
16. J. Li, M.Y. Zheng, W. Tang, P.L. He, W.L. Zhu, T.X. Li, J.P. Zuo, H. Liu, and H.L. Jiang Syntheses of triazole-modified zanamivir analogues via click chemistry and anti-AIV activities Bioorg. Med. Chem. Lett. 16 2006 5009 5013 (Pubitemid 44262496)
17. M. Chandler, R. Conroy, A.W.J. Cooper, R.B. Lamont, J.J. Scicinski, J.E. Smart, R. Storer, N.G. Weir, R.D. Wilson, and P.G. Wyatt Approaches to carbocyclic analogues of the potent neuraminidase inhibitor 4-guanidino- Neu5Ac2en. X-Ray molecular structure of N-[(1S,2S,6R)-2-azido-6-benzyloxymethyl- 4-formylcyclohex-3-enyl]acetamide J. Chem. Soc. Perkin Trans. 1 1995 1189 1197
18. D.J. Ye, J. Li, J. Zhang, H. Liu, and H.L. Jiang Simultaneous stereoselective 4-amination with cyclic secondary amines and 2-O-deacetylation of peracetylated sialic acid derivatives Tetrahedron Lett. 48 2007 4023 4027 (Pubitemid 46711202)
19. D.J. Ye, G.H. Deng, W.F. Liu, Y. Zhou, E.G. Feng, H.L. Jiang, and H. Liu Simultaneous 2-O-deacetylation and 4-amination of peracetylated Neu5Ac: application to the synthesis of (4/4)-piperazine derivatives linked sialic acid dimers Tetrahedron 64 2008 6544 6550
20. 2O J. Org. Chem. 74 2009 1733 1735
21. W.J. Shin, K.H. Lee, M.H. Park, and B.L. Seong Broad-spectrum antiviral effect of Agrimonia pilosa extract on influenza viruses Microbiol. Immunol. 54 2010 11 19
22. T. Lu, T. Markotan, F. Coppo, B. Tomczuk, C. Crysler, S. Eisennagel, J. Spurlino, L. Gremminger, R.M. Soll, E.C. Giardino, and R. Bone Oxyguanidines. Part 2: discovery of a novel orally active thrombin inhibitor through structure-based drug design and parallel synthesis Bioorg. Med. Chem. Lett. 14 2004 3727 3731 (Pubitemid 38760070)
23. S. Tasler, O. Muller, T. Wieber, T. Herz, R. Krauss, F. Totzke, M.H. Kubbutat, and C. Schachtele N-substituted 2′-(aminoaryl)benzothiazoles as kinase inhibitors: hit identification and scaffold hopping Bioorg. Med. Chem. Lett. 19 2009 1349 1356
24. S.J. Macdonald, R. Cameron, D.A. Demaine, R.J. Fenton, G. Foster, D. Gower, J.N. Hamblin, S. Hamilton, G.J. Hart, A.P. Hill, G.G. Inglis, B. Jin, H.T. Jones, D.B. McConnell, J. McKimm-Breschkin, G. Mills, V. Nguyen, I.J. Owens, N. Parry, S.E. Shanahan, D. Smith, K.G. Watson, W.Y. Wu, and S.P. Tucker Dimeric zanamivir conjugates with various linking groups are potent, long-lasting inhibitors of influenza neuraminidase including H5N1 avian influenza J. Med. Chem. 48 2005 2964 2971 (Pubitemid 40548109)
25. L. Venkatramani, E. Bochkareva, J.T. Lee, U. Gulati, W. Graeme Laver, A. Bochkarev, and G.M. Air An epidemiologically significant epitope of a 1998 human influenza virus neuraminidase forms a highly hydrated interface in the NA-antibody complex J. Mol. Biol. 356 2006 651 663 (Pubitemid 43139327)
26. V. Stoll, K.D. Stewart, C.J. Maring, S. Muchmore, V. Giranda, Y.G. Gu, G. Wang, Y. Chen, M. Sun, C. Zhao, A.L. Kennedy, D.L. Madigan, Y. Xu, A. Saldivar, W. Kati, G. Laver, T. Sowin, H.L. Sham, J. Greer, and D. Kempf Influenza neuraminidase inhibitors: structure-based design of a novel inhibitor series Biochemistry 42 2003 718 727 (Pubitemid 36133296)
27. E.J. Jung, K.H. Lee, and B.L. Seong Reverse genetic platform for inactivated and live-attenuated influenza vaccine Exp. Mol. Med. 42 2010 116 121
28. E.A. Govorkova, I.A. Leneva, O.G. Goloubeva, K. Bush, and R.G. Webster Comparison of efficacies of RWJ-270201, zanamivir, and oseltamivir against H5N1, H9N2, and other avian influenza viruses Antimicrob. Agents Chemother. 45 2001 2723 2732 (Pubitemid 32906663)