Research on Chemical Intermediates

, Volume 40, Issue 4, pp 1365–1381

Synthesis and anti-viral activities of some 3-(naphthalen-1-ylmethylene)-5-phenylfuran-2(3H)-one candidates

  • Eman M. Flefel
  • Waled A. Tantawy
  • Randa E. Abdel-Mageid
  • Abd El-Galil E. Amr
  • Rolla Nadeem
Article

Abstract

3-(Naphthalen-1-ylmethylene)-5-phenylfuran-2(3H)-one 1 was prepared and converted into a variety of heterocyclic systems of synthetic and biological importance. Benzylamine was reacted with furanone 1 to afford compounds 2 and 3 according to the reaction conditions. Butanamide 2 was reacted with thionyl chloride or thiourea to give derivatives 4 and 5, respectively. Compound 3 was reacted with ethyl cyanoacetate to give the corresponding pyrrolopyridine derivative 6. Treatment of 1 with hydrazine hydrate afforded compounds 7 and 8 according to the reaction conditions. Also, compound 1 was reacted with phenyl hydrazine, hydroxyl amine, malononitrile or thiourea to give compounds 912, respectively. Cyclization of 7 with ethoxymethylene-malononitrile, ethyl-(ethoxymethylene)cyanoacetate, carbon disulphide or acetylacetone afforded the corresponding compounds 1316, respectively. Condensation of 7 with p-nitrobenzaldehyde gave the corresponding hydrazone 17, which was treated with thioglycolic acid or chloroacetyl chloride to give compounds 18 and 19, respectively. Also, most of the prepared products were tested for anti-avian influenza virus and revealed promising antiviral activity against H5N1 virus [A/Chicken/Egypt/1/2006 (H5N1)] by determination of both TC50 and ED50 and confirmed by plaque reduction assay on MDCK cells. Compounds 7, 8, 11, 12 and 13 showed the highest effect compared with the other tested compounds.

Keywords

Furanone Acid hydrazide Anti-avian influenza virus (H5N1) 

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Copyright information

© Springer Science+Business Media Dordrecht 2013

Authors and Affiliations

  • Eman M. Flefel
    • 1
  • Waled A. Tantawy
    • 1
  • Randa E. Abdel-Mageid
    • 1
  • Abd El-Galil E. Amr
    • 2
    • 3
  • Rolla Nadeem
    • 4
  1. 1.Department of PhotochemistryNational Research CentreCairoEgypt
  2. 2.Pharmaceutical Chemistry Department, Drug Exploration & Development Chair (DEDC)College of Pharmacy, King Saud UniversityRiyadhSaudi Arabia
  3. 3.Applied Organic Chemistry DepartmentNational Research CenterCairoEgypt
  4. 4.Virology Laboratory, Environmental Research DivisionNational Research CenterCairoEgypt

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