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Monatshefte für Chemie - Chemical Monthly

, Volume 141, Issue 9, pp 1021–1028 | Cite as

Synthesis and antiviral evaluation of new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their acyclic nucleoside analogues

  • Wael A. El-Sayed
  • Farag A. El-Essawy
  • Omar M. Ali
  • Barsis S. Nasr
  • Mohamed M. Abdalla
  • Adel A.-H. Abdel-RahmanEmail author
Original Paper

Abstract

A number of new 5-[(naphthalen-1-yloxy)-methyl]-1,3,4-oxadiazole derivatives were synthesized. Sugar 2-[5-[(naphthalen-1-yloxy)methyl]-1,3,4-oxadiazol-2-ylthio]acetohydrazones were prepared by condensation of the hydrazide with the corresponding monosaccharides. Cyclization of the sugar hydrazones with acetic anhydride afforded the substituted oxadiazoline derivatives. The synthesized compounds displayed different degrees of antiviral activities or inhibitory actions against HCV and HIV viruses.

Graphical abstract

Keywords

Sugar hydrazones 1,3,4-Oxadiazoles Acyclic nucleosides Antiviral agents 

References

  1. 1.
    Zareen A, Maimoona R, Choudhary MI, Supino Khan R, Khalid M, Atta-ur-Rahman (2004) Biophys Res Comm 319:1053Google Scholar
  2. 2.
    El-Azzouny AA, Maklad YA, Bartsch H, Zaghary WA, Ibrahim WM, Mohamed MS (2003) Sci Pharm 71:331Google Scholar
  3. 3.
    Loetchutinat C, Chau F, Mankhetkorn S (2003) Chem Pharm Bull 51:728CrossRefGoogle Scholar
  4. 4.
    Ates O, Kocabalkanli A, Sanis GO, Ekinci AC, Vidin A (1997) Drug Res 47:1134Google Scholar
  5. 5.
    Farghaly AR (2004) J Chin Chem Soc 51:147Google Scholar
  6. 6.
    Li XZZ, Wang Y, Chen W, Huang Q, Liu C, Song G (2003) J Fluor Chem 123:163CrossRefGoogle Scholar
  7. 7.
    Zou X, Zhang Z, Jin GJ (2002) J Chem Res (S) 228Google Scholar
  8. 8.
    Palaska E, Sahin G, Kelicen P, Durlu NT, Altinok G (2002) Il Farmaco 57:101CrossRefGoogle Scholar
  9. 9.
    Mhasalkar MY, Shah MH, Pilankar PD, Nikan ST, Anantanarayan KG, Deliwala CV (1071) J Med Chem 14:1000Google Scholar
  10. 10.
    Tyagi M, Kumar A (2002) Orient J Chem 18:125Google Scholar
  11. 11.
    El-Emam AA, Al-Deep AO, Al-Omar M, Lehmann J (2004) Bioorg Med Chem 12:5107CrossRefGoogle Scholar
  12. 12.
    Liszkiewicz H, Kowalska MW, Wietrzyk J, Opolski A (2003) Indian J Chem Sec B-Org Chem Incl Med Chem 42:2846Google Scholar
  13. 13.
    Holy A (1987) Nucleosides Nucleotides 6:147CrossRefGoogle Scholar
  14. 14.
    Remy RJ, Secrist JA (1985) Nucleosides Nucleotides 4:411CrossRefGoogle Scholar
  15. 15.
    Larson A, Alenius S, Johnsson NG, Oberg B (1983) Antiviral Res 3:77CrossRefGoogle Scholar
  16. 16.
    El Ashry ESH, El Kilany Y (1996) Adv Heterocycl Chem 67:391CrossRefGoogle Scholar
  17. 17.
    El Ashry ESH, El Kilany Y (1997) Adv Heterocycl Chem 68:1CrossRefGoogle Scholar
  18. 18.
    El Ashry ESH, El Kilany Y (1998) Adv Heterocycl Chem 69:129CrossRefGoogle Scholar
  19. 19.
    Chu CK, Cutler SJ (1986) J Heterocycl Chem 23:89Google Scholar
  20. 20.
    Markar GM, Keseru GM (1997) J Med Chem 40:4154CrossRefGoogle Scholar
  21. 21.
    Franchetti P, Cappellacci L, Abu Sheikha G, Jayaram HN, Gurudutt VV, Sint T, Schneider BP, Jones WD, Goldstein BM, Perra G, DeMontis A, Loi AG, LaColla P, Grifantini M (1997) J Med Chem 40:1731CrossRefGoogle Scholar
  22. 22.
    Hammerschmidt F, Peric B, Ohler E (1997) Monatsh Chem 128:183CrossRefGoogle Scholar
  23. 23.
    El-Essawy FA, El-Sayed WA, El-Kafrawy SA, Morshedy AS, Abdel-Rahman AAH (2008) Z Naturforsch 63C:667Google Scholar
  24. 24.
    Ali OM, Amer HH, Abdel-Rahman AAH (2007) Synthesis 2823Google Scholar
  25. 25.
    El-Sayed WA, Fathi NM, Gad WA, El Ashry ESH (2008) J Carbohydr Chem 27:357CrossRefGoogle Scholar
  26. 26.
    Kalluraya B, Shetty SN (1991) J Indian Chem Soc 68:424Google Scholar
  27. 27.
    Abdel-Aal MT, El-Sayed WA, El-Kosy SM, El Ashry ESH (2008) Arch Pharm Chem Life Sci 341:307CrossRefGoogle Scholar
  28. 28.
    Abdel-Aal MT, El-Sayed WA, El Ashry ESH (2006) Arch Pharm Chem Life Sci 339:356CrossRefGoogle Scholar
  29. 29.
    Somogyi L (1978) Carbohydr Res 64:289CrossRefGoogle Scholar
  30. 30.
    Somogyi L (1977) Carbohydr Res 54:C14CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Wael A. El-Sayed
    • 1
  • Farag A. El-Essawy
    • 2
  • Omar M. Ali
    • 2
  • Barsis S. Nasr
    • 2
  • Mohamed M. Abdalla
    • 3
  • Adel A.-H. Abdel-Rahman
    • 2
    Email author
  1. 1.Photochemistry DepartmentNational Research CenterCairoEgypt
  2. 2.Department of Chemistry, Faculty of ScienceMenoufia UniversityShebin El-KoamEgypt
  3. 3.Research UnitUnivet Pharmaceutical Co.CairoEgypt

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