title: Synthesis, antimicrobial, and antiviral activities of some new 5-sulphonamido-8-hydroxyquinoline derivatives.
abstract: 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 (TCID(50)) and LTV of 500 TCID(50) 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 (IC(50)) range of 3-4 μg per egg against avian APMV-1 and LTV and their toxic concentration fifty (CC(50)) of 200-300 μg per egg.
authors.affiliation: Department of Therapeutic Chemistry, National Research Centre, Dokki 12622, Giza, Egypt.
authors.forename: Emad M
authors.initials: EM
authors.lastname: Kassem
authors.forename: Eslam R
authors.initials: ER
authors.lastname: El-Sawy
authors.forename: Howaida I
authors.initials: HI
authors.lastname: Abd-Alla
authors.forename: Adel H
authors.initials: AH
authors.lastname: Mandour
authors.forename: Dina
authors.initials: D
authors.lastname: Abdel-Mogeed
authors.forename: Mounir M
authors.initials: MM
authors.lastname: El-Safty
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002642:Chick Embryo; D002522:Chlorocebus aethiops; D003588:Cytopathogenic Effect, Viral; D004926:Escherichia coli / Q000187:drug effects / Q000254:growth & development; D001352:Herpesvirus 1, Gallid / Q000187:drug effects / Q000254:growth & development; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009522:Newcastle disease virus / Q000187:drug effects / Q000254:growth & development; D015125:Oxyquinoline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology*; D014709:Vero Cells
chemical_list: D000890:Anti-Infective Agents; D000998:Antiviral Agents; D013449:Sulfonamides; D015125:Oxyquinoline