Acta Pharm. 62 (2012) 593-606

 

full paper

Short communication

 

Heterocyclic compounds based on 3-(4-bromophenyl) azo-5-phenyl-2(3H)-furanone: Anti-avian influenza virus (H5N1) activity

EMAN M. FLEFEL, RANDA E. ABDEL-MAGEID, WALED A. TANTAWY, MOHAMED A. ALI and ABD EL-GALIL E. AMR

emanflefel@yahoo.com

1 Department of Photochemistry, National Research Centre, Cairo, Egypt

2 Virology Laboratory, Environmental Research Division, National Research Center, Cairo, Egypt

3 Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia

4 Applied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt

Accepted September 10, 2012

 

3-[2-(4-Bromphenyl)hydrazono]-5-phenyl-furan-2(3H)-one (1) was used for preparation of some novel pyrazole, pyridazinone, oxadiazole, triazole, thiazolidine and thioxo-pyrimidine derivatives. Some of the prepared products were tested for anti-avian influenza virus activity and revealed promising antiviral activity against H5N1 virus [A/Chicken/Egypt/1/20 % (H5N1)] by determination of both EC50 and LD50 and confirmed by plaque reduction assay on MDCK cells. Compounds 3-[2-(4-bromophenyl)hydrazono]-5-phenylfuran-2(3H)-one 1, 1-(4-bromophenyl)-N-hydroxy-5-phenyl-1H-pyrazole-3-carboxamide 5 and 1-(4-bromophenyl)-N-{2,3-dihydro-4-hydroxy-3-phenyl-6-oxo-2-thioxopyrimidin-1(6H)-yl}-5-phenyl-1H-pyrazole-3-carboxamide (12a) showed the highest effects. Detailed synthesis, spectroscopic data, and antiviral activity of the synthesized compounds are reported.

 

Keywords: furanone, pyrazole, pyridazinone, oxadiazole, triazole, anti-avian influenza virus (H5N1)