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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

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Volume 62, Issue 4


Heterocyclic compounds based on 3-(4-bromophenyl) azo-5-phenyl-2(3H)-furanone: Anti-avian influenza virus (H5N1) activity / Heterociklički derivati 3-(4-bromfenil) azo-5-fenil-2(3H)-furanona: Djelovanje na virus ptičje gripe (H5N1)

Eman M. Flefel / Randa E. Abdel-Mageid / Waled A. Tantawy / Mohamed A. Ali / Abd El-Galil E. Amr
  • Drug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
  • Applied Organic Chemistry Department, National Research Center, Dokki 12622 Cairo, Egypt
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2013-01-15 | DOI: https://doi.org/10.2478/v10007-012-0037-7


3-[2-(4-Bromphenyl)hydrazono]-5-phenyl-furan-2(3H)-one () was used for preparation of some novel pyrazole, pyridazinone, oxadiazole, triazole, thiazolidine and thioxopyrimidine 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 Madin-Darby canine kidney 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.


3-[2-(4-Bromfenil)hidrazono]-5-fenil-furan-2(3H)-on () upotrjebljen je za pripravu novih derivata pirazola, piridazinona, oksadiazola, triazola, tiazolidina i tioksopirimidina. Neki od sintetiziranih spojeva imaju virustatski učinak na virus ptičje gripe H5N1. Farmakološki aktivnim spojevima određeni su EC50 i LD50 i dobiven je pozitivni test redukcije plaka na MDCK staničnoj liniji. Najjači učinak pokazali su 3-[2-(4-bromfenil)hidrazono]-5-fenilfuran-2(3H)-on (1), 1-(4-bromfenil)-N-hidroksi-5-fenil-1H-pirazol-3-karboksamid (5) i 1-(4-bromfenil)-N-{2,3-dihidro-4-hidroksi-3-fenil-6-okso-2-tioksopirimidin-1(6H)-il}-5-fenil-1H-pirazol-3-karboksamid (12a).

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

Ključne riječi: furanon; pirazol; piridazinon; oksadiazol; triazol; virus ptičje gripe (H5N1); virustatski učinak

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About the article

Published Online: 2013-01-15

Published in Print: 2012-12-01

Citation Information: Acta Pharmaceutica, Volume 62, Issue 4, Pages 593–606, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: https://doi.org/10.2478/v10007-012-0037-7.

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