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Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

4 Issues per year


IMPACT FACTOR 2016: 1.288
5-year IMPACT FACTOR: 1.600

CiteScore 2016: 1.55

SCImago Journal Rank (SJR) 2016: 0.353
Source Normalized Impact per Paper (SNIP) 2016: 0.854

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ISSN
1846-9558
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Volume 62, Issue 4 (Dec 2012)

Issues

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

1

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.

1

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

  • 1. A. I. Hashem, A. S. A. Youssef, K. A. Kandeel and W. S. I. Abou-Elmaged, Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity, Eur. J. Med. Chem. 42 (2007) 934-939; DOI: 10.1016/j.ejmech.2006.12.032.CrossrefWeb of ScienceGoogle Scholar

  • 2. A. I. Hashem, K. A. Kandeel, A. S. A. Youssef and W. S. I. Abou-Elmaged, Behaviour of some 2(3H)-furanones bearing a pyrazolyl group as alkylating agents, J. Chem. Res. 3 (2006) 315-317; DOI: 10.3184/030823406777411115.CrossrefGoogle Scholar

  • 3. M. S. Christodoulou, S. Liekens, K. M. Kasiotis and S. A. Haroutounian, Novel pyrazole derivatives: Synthesis and evaluation of anti-angiogenic activity, Bioorg. Med. Chem. 18 (2010) 4338-4350; DOI: 10.1016/j.bmc.2010.04.076.CrossrefGoogle Scholar

  • 4. A. Y. Shaw, H. H Liau, P. J. Lu, C. N. Yang, C. H. Lee, J. Y. Chen, Z. Xu and G. Flynn, 3,5-Diaryl-1H-pyrazole as a molecular scaffold for the synthesis of apoptosis-inducing agents, Bioorg. Med. Chem. 18 (2010) 3270-3278; DOI: 10.1016/j.bmc.2010.03.016.CrossrefGoogle Scholar

  • 5. J. Choi, Y. Park, H. S. Lee, Y. Yang and S. Yoon, 1,3-Diphenyl-1H-pyrazole derivatives as a new series of potent PPARg partial agonists, Bioorg. Med. Chem. 18 (2010) 8315-8323; DOI: 10.1016/j.bmc.2010.09.068.CrossrefGoogle Scholar

  • 6. A. Mohammad, K. Harish and S. A. Javed, Pharmacological activities of pyrazole and its derivatives, Hamdard Medicus 52 (2009) 102-118.Google Scholar

  • 7. A. El Maatougui, J. Azuaje, E. Sotelo, O. Caamaño and A. Coelho, Silica-supported aluminum chloride-assisted solution phase synthesis of pyridazinone-based antiplatelet agents, ACS Comb. Sci. 10 (2011) 7-12.Google Scholar

  • 8. A. A. Siddiqui, R. Mishra, M. Shaharyar, A. Husain, M. Rashid and P. Pal, Triazole incorporated pyridazinones as a new class of antihypertensive agents: Design, synthesis and in vivo screening, Bioorg. Med. Chem. Lett. 21 (2011) 1023-1026; DOI: 10.1016/j.bmcl.2010.12.028.Web of ScienceCrossrefGoogle Scholar

  • 9. I. H. R. Tomi, A. H. J. Al-Qaisi and Z. H. J. Al-Qaisi, Synthesis, characterization and effect of bis-1,3,4-oxadiazole rings containing glycine moiety on the activity of some transferase enzymes, J. King Saud. Univ. Sci. 23 (2011) 23-33; DOI: 10.1016/j.jksus.2010.06.002.CrossrefGoogle Scholar

  • 10. U. Ghani and N. Ullah, New potent inhibitors of tyrosinase: Novel clues to binding of 1,3,4-thiadiazole-2(3H)-thiones, 1,3,4-oxadiazole-2(3H)-thiones, 4-amino-1,2,4-triazole-5(4H)-thiones, and substituted hydrazides to the dicopper active site, Bioorg. Med. Chem. 18 (2010) 4042-4048; DOI: 10.1016/j.bmc.2010.04.021.CrossrefGoogle Scholar

  • 11. X. J. Zou, L. H. Lai, G. Y. Jin and Z. X. J. Zhang, Synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles, Agr. Food Chem. 50 (2002) 3757-3760; DOI: 10.1021/jf0201677.CrossrefGoogle Scholar

  • 12. G. V. S. Kumar, Y. Rajendraprasad, B. P. Mallikarjuna, S. M. Chandrashekar and C. Kistayya, Synthesis of some novel 2-substituted-5-[isopropylthiazole clubbed] 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents, Eur. J. Med. Chem. 45 (2010) 2063-2074; DOI: 10.1016/j.ejmech.2010.01.045.CrossrefGoogle Scholar

  • 13. K. Imtiaz, A. Sajid, H. Shahid, H. R. Nasim, T. H. Muhammad, W. Abdul, U. Reaz, U. Zaheer, K. Ajmal, A. M. Sajjad and C. Iqbal, Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives, Eur. J. Med. Chem. 45 (2010) 5200-5207; DOI: 10.1016/j.ejmech.2010.08.034.CrossrefGoogle Scholar

  • 14. M. McDowell, S. R. Gonzales, S. C. Kumarapperuma, M. Jeselnik, J. B. Arterburn and K. A. Hanley, A novel nucleoside analog, 1-b-D-ribofuranosyl-3-ethynyl-[1,2,4]triazole (ETAR), exhibits efficacy against a broad range of flaviviruses in vitro, Antivir. Res. 87 (2010) 78-80; DOI: 10.1016/j.antiviral.2010.04.007.Web of ScienceCrossrefGoogle Scholar

  • 15. H. P. Hsieh and J. T. Hsu, Pyrazole compound BPR1P0034 with potent and selective anti-influenza virus activity, Curr. Pharm. Design 13 (2007) 3531-3542; DOI: 10.1186/1423-0127-17-13.CrossrefGoogle Scholar

  • 16. A. E. Rashad, A. H. Shamroukh, R. E. Abdel-Megeid, A. Mostafa, M. A. Ali and K. Banert, A facile synthesis and anti-avian influenza virus (H5N1) screening of some novel pyrazolopyrimidine nucleoside derivatives, Nucleos. Nucleot. Nucl. 29 (2010) 809-820; DOI: 10.1080/15257770.2010.529480.CrossrefGoogle Scholar

  • 17. K. Hertogs, M. P. Béthune, V. Miller, T. Ivens, P. Schel, A. Van Cauwenberge, C. Van den Eynde, V. van Gerwen, H. Azijn, M. van Houtte, F. Peeters, S. Staszewski, M. Conant, S. Bloor, S. Kemp, B. Larder and R. Pauwels, A rapid method for simultaneous detection of phenotypic resistance to inhibitors of protease and reverse transcriptase in recombinant human immunodeficiency virus type 1 isolates from patients treated with antiretroviral drugs, Antimicrob. Agents Chemother. 42 (1998) 269-276.Google Scholar

  • 18. F. G. Hayden, Plaque inhibition assay for drug susceptibility testing of influenza viruses, Agents Chemother. 17 (1980) 865-870.Google Scholar

About the article

Published Online: 2013-01-15

Published in Print: 2012-12-01


Citation Information: Acta Pharmaceutica, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: https://doi.org/10.2478/v10007-012-0037-7.

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