Ahmed A. Fadda 1 , Aya R. Mohammed 1 , Ebrahim Abdel-Galil 1, *
Chemistry Department, Faculty of Science, Mansoura University, El-Gomhoria Street, ET-35516 Mansoura, Egypt
*corresponding author e-mail address: msebrahim2002@yahoo.com | Scopus ID 22957266700
Biointerface Research in Applied Chemistry, Volume 10, Issue 1, 2020, 4846 – 4852, https://doi.org/10.33263/BRIAC101.846852
ABSTRACT
Ten new compounds of quinoline clubbed with sulfonamide moiety were synthesized to be used as antimicrobial agents. Therefore, the diazotized N-(pyrimidin-2-yl)-benzenesulfonamide was diazocoupled with 8-hydroxyquinoline to furnish 4-(8-hydroxyquinolin-5-yl)-N-(pyrimidin-2-yl)benzenesulfonamide (3) which underwent chloroacetylation by chloroacetyl chloride to give the corresponding O-chloroacetylated product 6. The reactions of quinolinyl 2-chloroacetate derivative 6 with different nucleophiles (ethyl 2-mercaptoacetate, 2-mercapto-4,6-dimethylnicotinonitrile, o-aminothiophenol and/or malononitrile) were studied and utilized to pick up various heterocyclic systems 7, 10, 12 and 14. The chemical structures of newly prepared quinoline-containing scaffolds have been confirmed based on their spectral data (IR, 1H NMR and MS) and have been tested for their antimicrobial activity. The results showed that compounds 5d, 6, 7 and 14 displayed the highest activity against Gram-positive bacteria..
Keywords: Sulfonamides; 8-Hydroxyquinoline; Chloroacetyl chloride; Malononitrile; Antimicrobial activity.