Design, Synthesis and Biological Activity of Novel Chalcone Derivatives as Anti-influenza Agents

doi:10.1007/s40242-015-5356-z

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (1): 28-34.doi: 10.1007/s40242-015-5356-z

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Design, Synthesis and Biological Activity of Novel Chalcone Derivatives as Anti-influenza Agents

SHI Fangyuan, FANG Hao, XU Wenfang

Department of Medicinal Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, P. R. China

Received:2015-09-14 Revised:2015-11-13 Online:2016-02-01 Published:2015-11-30
Contact: XU Wenfang E-mail:wenfxu@163.com
Supported by:
Supported by the National High-tech R&D Program of China(No.2014AA020523), the National Natural Science Foundation of China(Nos.21302111, 81373282, 21172134) and the China Postdoctoral Science Foundation Funded Project (Nos.2013M540558, 2014T70654).

Abstract

Abstract:

A series of novel chalcone derivatives was designed and synthesized via a suitable synthetic strategy in good yields using commercially available 2-amino-4-nitrophenol as an initiator. The structures of the target compounds were confirmed by means of ¹H NMR, ¹³C NMR and high-resolution mass spectrometry(HRMS). And the ability of the target compounds to inhibit influenza viruses was evaluated. These compounds showed moderate inhibitory activity against influenza A(H9N2 and H5N1) viruses. Within this series, compounds S14 and S15 with good potency(IC₅₀=40.3-51.5μmol/L) could be used as lead compounds in the future.

Key words: Influenza virus, Inhibitor, Chalcone, Biological activity

SHI Fangyuan, FANG Hao, XU Wenfang. Design, Synthesis and Biological Activity of Novel Chalcone Derivatives as Anti-influenza Agents[J]. Chemical Research in Chinese Universities, 2016, 32(1): 28-34.

References

[1] Pennisi E., Science, 1995, 270(5244), 1916
[2] Stevens J., Blixt O., Chen L. M., Donis R. O., Paulson J. C., Wilson I. A., Journal of Molecular Biology, 2008, 381(5), 1382
[3] de Wit E., Fouchier R. A., J. Clin. Virol., 2008, 41(1), 1
[4] Koopmans M., Wilbrink B., Conyn M., Natrop G., van der Nat H., Vennema H., Meijer A., van Steenbergen J., Fouchier R., Osterhaus A., Bosman A., Lancet, 2004, 363(9409), 587
[5] Lin Y. P., Shaw M., Gregory V., Cameron K., Lim W., Klimov A., Subbarao K., Guan Y., Krauss S., Shortridge K., Webster R., Cox N., Hay A., Proc. Natl. Acad. Sci. USA, 2000, 97(17), 9654
[6] Morton S. E., Mathai M., Byrd R. P. Jr., Fields C. L., Roy T. M., Southern Medical Journal, 2001, 94(1), 67
[7] Hay A. J., Wolstenholme A. J., Skehel J. J., Smith M. H., The EMBO Journal, 1985, 4(11), 3021
[8] 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., Antimicrobial Agents and Chemotherapy, 1998, 42(3), 640
[9] Deyde V. M., Xu X., Bright R. A., Shaw M., Smith C. B., Zhang Y., Shu Y., Gubareva L. V., Cox N. J., Klimov A. I., The Journal of Infectious Diseases, 2007, 196(2), 249
[10] de Jong M. D., Tran T. T., Truong H. K., Vo M. H., Smith G. J., Nguyen V. C., Bach V. C., Phan T. Q., Do Q. H., Guan Y., Peiris J. S., Tran T. H., Farrar J., The New England Journal of Medicine, 2005, 353(25), 2667
[11] Lackenby A., Hungnes O., Dudman S. G., Meijer A., Paget W. J., Hay A. J., Zambon M. C., Euro Surveillance:Bulletin Europeen Sur Les Ma-ladies Transmissibles(European Communicable Disease Bulletin), 2008, 13(5), 1
[12] Liu A. L., Wang H. D., Lee S. M., Wang Y. T., Du G. H., Bioorganic & Medicinal Chemistry, 2008, 16(15), 7141
[13] Upadhyay A., Chompoo J., Taira N., Fukuta M., Gima S., Tawata S., Journal of Agricultural and Food Chemistry, 2011, 59(24), 12858

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Design, Synthesis and Biological Activity of Novel Chalcone Derivatives as Anti-influenza Agents

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