Synthesis, antimicrobial, and antiviral activities of some new 5-sulphonamido-8-hydroxyquinoline derivatives
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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.
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- Synthesis, antimicrobial, and antiviral activities of some new 5-sulphonamido-8-hydroxyquinoline derivatives
Archives of Pharmacal Research
Volume 35, Issue 6 , pp 955-964
- Cover Date
- Print ISSN
- Online ISSN
- Pharmaceutical Society of Korea
- Additional Links
- 8-Hydroxyquinoline-5-sulphonyl chloride
- Pyrano(2,3-d) imidazole
- Antiviral activity
- Industry Sectors
- Author Affiliations
- 1. Department of Therapeutic Chemistry, National Research Centre, Dokki 12622, Giza, Egypt
- 2. Department of Natural Compounds Chemistry, National Research Centre, Dokki 12622, Giza, Egypt
- 3. Central Laboratory for Evaluation of Veterinary Biologics, Abbassia 13181, Cairo, Egypt