Skip to main content
SpringerLink
Log in

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

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

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

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. Zareen A, Maimoona R, Choudhary MI, Supino Khan R, Khalid M, Atta-ur-Rahman (2004) Biophys Res Comm 319:1053

  2. El-Azzouny AA, Maklad YA, Bartsch H, Zaghary WA, Ibrahim WM, Mohamed MS (2003) Sci Pharm 71:331

    CAS  Google Scholar 

  3. Loetchutinat C, Chau F, Mankhetkorn S (2003) Chem Pharm Bull 51:728

    Article  CAS  Google Scholar 

  4. Ates O, Kocabalkanli A, Sanis GO, Ekinci AC, Vidin A (1997) Drug Res 47:1134

    CAS  Google Scholar 

  5. Farghaly AR (2004) J Chin Chem Soc 51:147

    Google Scholar 

  6. Li XZZ, Wang Y, Chen W, Huang Q, Liu C, Song G (2003) J Fluor Chem 123:163

    Article  Google Scholar 

  7. Zou X, Zhang Z, Jin GJ (2002) J Chem Res (S) 228

  8. Palaska E, Sahin G, Kelicen P, Durlu NT, Altinok G (2002) Il Farmaco 57:101

    Article  CAS  Google Scholar 

  9. Mhasalkar MY, Shah MH, Pilankar PD, Nikan ST, Anantanarayan KG, Deliwala CV (1071) J Med Chem 14:1000

    Google Scholar 

  10. Tyagi M, Kumar A (2002) Orient J Chem 18:125

    CAS  Google Scholar 

  11. El-Emam AA, Al-Deep AO, Al-Omar M, Lehmann J (2004) Bioorg Med Chem 12:5107

    Article  CAS  Google Scholar 

  12. Liszkiewicz H, Kowalska MW, Wietrzyk J, Opolski A (2003) Indian J Chem Sec B-Org Chem Incl Med Chem 42:2846

    Google Scholar 

  13. Holy A (1987) Nucleosides Nucleotides 6:147

    Article  CAS  Google Scholar 

  14. Remy RJ, Secrist JA (1985) Nucleosides Nucleotides 4:411

    Article  CAS  Google Scholar 

  15. Larson A, Alenius S, Johnsson NG, Oberg B (1983) Antiviral Res 3:77

    Article  Google Scholar 

  16. El Ashry ESH, El Kilany Y (1996) Adv Heterocycl Chem 67:391

    Article  CAS  Google Scholar 

  17. El Ashry ESH, El Kilany Y (1997) Adv Heterocycl Chem 68:1

    Article  CAS  Google Scholar 

  18. El Ashry ESH, El Kilany Y (1998) Adv Heterocycl Chem 69:129

    Article  CAS  Google Scholar 

  19. Chu CK, Cutler SJ (1986) J Heterocycl Chem 23:89

    Google Scholar 

  20. Markar GM, Keseru GM (1997) J Med Chem 40:4154

    Article  Google Scholar 

  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 40:1731

    Article  CAS  Google Scholar 

  22. Hammerschmidt F, Peric B, Ohler E (1997) Monatsh Chem 128:183

    Article  CAS  Google Scholar 

  23. El-Essawy FA, El-Sayed WA, El-Kafrawy SA, Morshedy AS, Abdel-Rahman AAH (2008) Z Naturforsch 63C:667

    Google Scholar 

  24. Ali OM, Amer HH, Abdel-Rahman AAH (2007) Synthesis 2823

  25. El-Sayed WA, Fathi NM, Gad WA, El Ashry ESH (2008) J Carbohydr Chem 27:357

    Article  CAS  Google Scholar 

  26. Kalluraya B, Shetty SN (1991) J Indian Chem Soc 68:424

    CAS  Google Scholar 

  27. Abdel-Aal MT, El-Sayed WA, El-Kosy SM, El Ashry ESH (2008) Arch Pharm Chem Life Sci 341:307

    Article  CAS  Google Scholar 

  28. Abdel-Aal MT, El-Sayed WA, El Ashry ESH (2006) Arch Pharm Chem Life Sci 339:356

    Article  Google Scholar 

  29. Somogyi L (1978) Carbohydr Res 64:289

    Article  CAS  Google Scholar 

  30. Somogyi L (1977) Carbohydr Res 54:C14

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Photochemistry Department, National Research Center, El Dokki, Cairo, Egypt

    Wael A. El-Sayed

  2. Department of Chemistry, Faculty of Science, Menoufia University, Shebin El-Koam, Egypt

    Farag A. El-Essawy, Omar M. Ali, Barsis S. Nasr & Adel A.-H. Abdel-Rahman

  3. Research Unit, Univet Pharmaceutical Co., Cairo, Egypt

    Mohamed M. Abdalla

Authors
  1. Wael A. El-Sayed
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Farag A. El-Essawy
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Omar M. Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Barsis S. Nasr
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mohamed M. Abdalla
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Adel A.-H. Abdel-Rahman
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Adel A.-H. Abdel-Rahman.

Rights and permissions

Reprints and permissions

About this article

Cite this article

El-Sayed, W.A., El-Essawy, F.A., Ali, O.M. et al. Synthesis and antiviral evaluation of new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their acyclic nucleoside analogues. Monatsh Chem 141, 1021–1028 (2010). https://doi.org/10.1007/s00706-010-0360-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-010-0360-y

Keywords

Search

Navigation