Open AccessSynthesis and antimicrobial evaluation of some 4-quinolinylazo-N-pyrimidinyl benzenesulfonamide derivatives
Author(s) -
Ahmed A. Fadda,
Aya R. Mohammed,
Ebrahim AbdelGalil
Publication year - 2019
Publication title -
biointerface research in applied chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.216
H-Index - 11
ISSN - 2069-5837
DOI - 10.33263/briac101.846852
Subject(s) - quinoline , chloroacetyl chloride , chemistry , antimicrobial , malononitrile , sulfonamide , moiety , ethyl chloroacetate , combinatorial chemistry , sulfanilamide , medicinal chemistry , chloride , organic chemistry , catalysis , biochemistry , hydrate
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.