Skip to main content
Log in

Synthesis and Anti-H5N1 Activity of Substituted Pyridine Glycosides and (Oxadiazolyl)oxymethylpyridine Acyclic C-Nucleoside Analogues

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

New aryl- and heteroaryl-substituted pyridinyl sugar hydrazones and their derivatives, 1,3,4-oxadiazole acyclic C-nucleosides, were synthesized. Novel O-glycoside derivatives of the substituted pyridines were prepared. The antiviral activity against avian influenza H5N1 virus was studied and compounds 5a, 9a, and 14 demonstrated high inhibition activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Pleschka, S., Stein, M., Schoop, R., and Hudson, J.B., Virol. J., 2009, vol. 6, p. 197. doi. 10.1186/1743-422x-6-197

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Noah, J.W., Severson, W., Noah, D.L., Rasmussen, L., White, E.L., and Jonsson, C.B., Antiviral Res., 2007, vol. 73, p. 50. doi 10.1016/j.antiviral.2006.07.006

    Article  CAS  PubMed  Google Scholar 

  3. Ungchusak, K., Auewarakul, P., and Dowell, S.F., N. Engl. J. Med., 2005, vol. 352, p. 333. doi. 10.1056/NEJMoa044021

    Article  CAS  Google Scholar 

  4. Shih, S.R., Chu, T.Y., Reddy, G.R., Tseng, S.N., Chen, H.L., Tang, W.F., Wu, M.S., Yeh, J.Y., Chao, Y.S., Hsu, J.T., Hsieh, H.P., and Horng, J.T., J. Biomed. Sci., 2010, vol. 17, p. 13. doi. 10.1186/1423-0127-17-S1-S13

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. (a) Daly, J.W., Garraffo, H.M., and Spande, T.F., in Alkaloids: Chemical and Biological Perspectives, Pelletier, W.W., Ed., New York: Elsevier, 1999, vol. 13, p. 95.

    Google Scholar 

  6. Quin, L.D. and Tyrell, J.A., Fundamentals of Heterocyclic Chemistry, HobokenL Wiley, 2010, p. 204, ch. 8.3.

    Google Scholar 

  7. Li, T., Zhang, J., Pan, J., Wu, Z., Hu, D., and Song, B., Eur. J. Med. Chem., 2017, vol. 125, p. 657. doi 10.1016/j.ejmech.2016.09.069

    Article  CAS  PubMed  Google Scholar 

  8. El-Sayed, W.A., Khalaf, H.S., Mohamed, S.F., Hussien, H.A., Kutkat, O.M., and Amr, A.E.E., Russ. J. Gen. Chem., 2017, vol. 87, no. 10, p. 2444. doi 10.1134/S1070363217100279

    Article  CAS  Google Scholar 

  9. Kozlov, M.V., Kleymenova, A.A., Romanova, L.I., Konduktorov, K.A., Kamarov, K.A., Smirnova, O.A., Prassolov, V.S., and Kochetkov, S.N., Bioorg. Med. Chem. Lett., 2015, vol. 25, p. 2382. doi 10.1016/j.bmcl.2015.04.016

    Article  CAS  PubMed  Google Scholar 

  10. Son, J.-K. and Lee, E.-S. Eur. J. Med. Chem., 2008, vol. 43, p. 675. doi 10.1016/j.ejmech.2007.05.002

    Article  CAS  PubMed  Google Scholar 

  11. Hayakawa, M., Parker, P., and Workman, P., Bioorg. Med. Chem., 2007, vol. 15, p. 403. doi 10.1016/j.bmc.2006.09.047.

    Article  CAS  PubMed  Google Scholar 

  12. Romagnoli, R., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 5041. doi 10.1016/j.bmcl.2008.08.006

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Stegmeier, F., Warmuth, M., Sellers, W.R., and Dorsch, M., Clin. Pharmacol. Ther., 2010, vol. 87, p. 543. doi 10.1038/clpt.2009.297

    Article  CAS  PubMed  Google Scholar 

  14. Shi, F., Lee, C., Xia, M., Miao, K., Zhao, Y., Tu, S., Zheng, W., Zhang, G, and Ma, N., Bioorg Med. Chem. Lett., 2009, vol. 19, p. 5565. doi 10.1016/j.bmcl.2009.08.046

    Article  CAS  PubMed  Google Scholar 

  15. Ivachtchenko, A.V. and Kovalenko, S.M. Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 5483. doi 10.1016/j.bmcl.2005.08.081

    Article  CAS  PubMed  Google Scholar 

  16. Suksrichavalit, T., Prachayasittikul, S., Nantasenamat, C., Isarankura-Na-Ayudhya, C., and Prachayasittikul, V., Eur. J. Med. Chem., 2009, vol. 44, p. 3259. doi 10.1016/j.ejmech.2009.03.033

    Article  CAS  PubMed  Google Scholar 

  17. Bahekar, R.H., Jain, M.R., Jadav, P.A., Prajapati, V.M., Patel, D.N., Gupta, A.A, Sharma, R., Tom, D., Bandyopadhya, H., and Modi, P.R., and Patel, P.R., Bioorg. Med. Chem., 2007, vol. 15, p. 6782. doi org/10.1016/. j.bmc.2007.08.005

    Article  CAS  PubMed  Google Scholar 

  18. McCrae, C.S., Ross, A., Stripling, A., and Dautovich, N.D., Clin. Interventions Aging, 2007, vol. 2, p. 313.

    CAS  Google Scholar 

  19. Harrison, T.S. and Scott, L. J. Drugs, 2005, vol. 65, p. 2309. doi 10.2165/00003495-200565160-00010

    Article  CAS  Google Scholar 

  20. Eastell, R., Vrijens, B., Cahall, D.L., Ringe, J.D., Garnero, P., and Watts, N.B., J. Bone Miner. Res., 2011, vol. 26, p. 1662. doi 10.1002/jbmr.342

    Article  CAS  PubMed  Google Scholar 

  21. Watts, G.F. and Chan, D.C. Arterioscler Thromb. Vasc. Biol., 2008, vol. 28, p. 1892. doi 10.1161/ATVBAHA.108.175224

    Article  CAS  PubMed  Google Scholar 

  22. Smith, U., Int. J. Clin. Pract. Suppl., 2001, vol. 121, p. 13.

    CAS  Google Scholar 

  23. Horak, F., Stübner, U.P., Zieglmayer, R., and Harris, A.G., J. Allergy Clin. Immunol., 2002, vol. 109, p. 956. doi 10.1067/mai.2002.124657

    Article  CAS  PubMed  Google Scholar 

  24. Metz, D.C., Vakily, M., Dixit, T., and Mulford, D., Aliment. Pharmacol. Ther., 2009, vol. 29, p. 928. doi 10.1111/j.1365-2036.2009.03984

    Article  CAS  PubMed  Google Scholar 

  25. Kubota, T., Nishi, T., Fukushi, E., Kawabata, J., Fromont, J., Kobayashi, and Nakinadine, A. Tetrahedron Lett., 2007, vol. 48, p. 4983. doi 10.1002/chin.200745187

    Article  CAS  Google Scholar 

  26. Dewick, P.M., Medicinal Natural Products: A Biosynthetic Approach, Chichester: Wiley, 2009, 3rd ed., p. 331, ch. 6.

    Book  Google Scholar 

  27. Kumar, G.V.S. and Prasad, Y.R., Med. Chem. Res., 2013, vol. 22, p. 4239. doi 10.1007/s00044-012-0431-1

    Article  CAS  Google Scholar 

  28. El-Sayed, W.A., El-Sofany, W.I., Hussein, H.A., and Fathi, N.M., Nucleosides, Nucleotides and Nucleic Acids, 2017, vol. 36, p. 474. doi 10.1080/15257770.2017.1327665

    Article  CAS  PubMed  Google Scholar 

  29. El-Sayed, W.A., Khalaf, H.S., Osman, D.A.A., Abbas, H.-A.S., and Ali, M.M., Acta Polonea Pharmaceutica-Drug Res., 2017, vol. 74, p. 1739.

    Google Scholar 

  30. El-Essawy, F.A., El-Sayed, W.A., Morshedy, A.S., and Abdel-Rahman, A.A.-H., Z. Naturforsch. C, 2008, vol. 63, p. 667.

    Article  CAS  PubMed  Google Scholar 

  31. Fadda, A.A., Abdel-Rahman, A.A.-H., El-Sayed, W.A., Zidan T.A., and Badria F.A., Chem. Heterocycl. Comp., 2011, vol. 47, p. 856. doi. 10.1007/s10593-011-0847-4

    Article  CAS  Google Scholar 

  32. Li, Z., Zhan, P., and Liu, X.. Mini-Rev. Med. Chem., 2011, vol. 11, p. 1130. doi 10.2174/138955711797655407

    Article  CAS  PubMed  Google Scholar 

  33. El-Sayed, W.A., Fathi, N.M., Gad, W.A., and El-Ashry, E.S.H., J. Carbohydr. Chem., 2008, vol. 27, p. 357. doi 10.1080/07328300802262778

    Article  CAS  Google Scholar 

  34. El-Sayed, W.A., El-Essawy, F.A., Ali, O.M., Barsis, A.M., and Abdel-Rahman, A.A.-H., Monats. Chem. Chem. Mon., 2010, vol. 141, p. 1021. doi 10.1007/s00706-010-0360-y

    Article  CAS  Google Scholar 

  35. Genini, D., Adachi, S., Chao, Q., Rose, D.W., Carrera, C.J., Cottam, H.B., Carson, D.A., and Leoni, L.M., Blood, 2000, vol. 96, p. 3537.

    CAS  PubMed  Google Scholar 

  36. El-Sayed, H.A., Moustafa, A.H., Haikal, A.Z., Abdou, I.M., and El-Ashry, E.S.H. Nucleosides, Nucleotides and Nucleic Acids, 2008, vol. 27, p. 1061. doi 10.1080/15257770802271805

    Article  CAS  PubMed  Google Scholar 

  37. Mossman, T., J. Immunol. Methods, 1983, vol. 65, nos. 1–2, p. 55.

    Article  Google Scholar 

  38. Haydenof, F.G., Cote, K.M., and Douglas, R.G., Antimicrob. Agents Chemother., 1980, vol. 17, p. 865.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. R. Kotb.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Soliman, H.A., Kotb, E.R., El-Bayaa, M.N. et al. Synthesis and Anti-H5N1 Activity of Substituted Pyridine Glycosides and (Oxadiazolyl)oxymethylpyridine Acyclic C-Nucleoside Analogues. Russ J Gen Chem 88, 815–824 (2018). https://doi.org/10.1134/S1070363218040291

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218040291

Keywords

Navigation