Archives of Pharmacal Research

, Volume 35, Issue 6, pp 955–964

Synthesis, antimicrobial, and antiviral activities of some new 5-sulphonamido-8-hydroxyquinoline derivatives


  • Emad M. Kassem
    • Department of Therapeutic ChemistryNational Research Centre
  • Eslam R. El-Sawy
    • Department of Natural Compounds ChemistryNational Research Centre
    • Department of Natural Compounds ChemistryNational Research Centre
  • Adel H. Mandour
    • Department of Natural Compounds ChemistryNational Research Centre
  • Dina Abdel-Mogeed
    • Department of Therapeutic ChemistryNational Research Centre
  • Mounir M. El-Safty
    • Central Laboratory for Evaluation of Veterinary Biologics
Research Articles Drug Design and Discovery

DOI: 10.1007/s12272-012-0602-0

Cite this article as:
Kassem, E.M., El-Sawy, E.R., Abd-Alla, H.I. et al. Arch. Pharm. Res. (2012) 35: 955. doi:10.1007/s12272-012-0602-0


A series of fused pyranopyrazole and pyranoimidazole, namely 5-(3,6-diamino-4-aryl-5-carbonitrile-pyrano(2,3-c)pyrazol-2-yl)sulphonyl-8-hydroxyquinolines (5a–e), 5-(6-amino-4-aryl-5-carbonitrile-pyrano(2,3-c)pyrazol-3-yl)sulphonamido-8-hydroxyquinolines (6a-e), 5-(2-thioxo-4-aryl-5-carbonitrile-6-amino-pyrano(2,3-d)imidazol-2-yl)sulphonyl-8-hydroxyquinolines (10a-e), and 5-(2-oxo-4-aryl-5-carbonitrile-6-amino-pyrano(2,3-d)imidazol-2-yl) sulphonyl-8-hydroxyquinolines (11a-e), have been prepared via condensation of some arylidine malononitriles with 5-sulphonamido-8-hydroxyquinoline derivatives 3, 4, 8 and 9. All the synthesized compounds were screened for their antimicrobial activities, and most of the tested compounds showed potent inhibition growth activity towards Escherichia coli, Pseudomonas aeruginosa (Gramnegative bacteria). Furthermore, six selected compounds were tested for their antiviral activity against avian paramyxovirus type1 (APMV-1) and laryngotracheitis virus (LTV), and the results showed that a concentration range of 3-4 μg per mL of compounds 2, 3, and 4 showed marked viral inhibitory activity for APMV-1 of 5000 tissue culture infected dose fifty (TCID50) and LTV of 500 TCID50 in Vero cell cultures based on their cytopathic effect. Chicken embryo experiments show that compounds 2, 3, and 4 possess high antiviral activity in vitro with an inhibitory concentration fifty (IC50) range of 3–4 μg per egg against avian APMV-1 and LTV and their toxic concentration fifty (CC50) of 200–300 μg per egg.

Key words

8-Hydroxyquinoline-5-sulphonyl chloridePyrano(2,3-c)pyrazolePyrano(2,3-d) imidazoleAntimicrobialAntiviral activity
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© The Pharmaceutical Society of Korea and Springer Netherlands 2012