M. Ghorab, A. M. Soliman, M. Alsaid
Jun 6, 2017
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Journal
Arabian Journal of Chemistry
Abstract
Abstract A new series of 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)- N -(substituted)benzenesulfonamide 3 – 17 , monosubstituted 2-((4-((4-aminophenyl)sulfonyl)phenyl)amino)methylene 18 , and its disubstituted derivative 19 were synthesized from the starting material 2-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione 2 . The crystal structures of compounds 2 , 7 and 13 were reported by us through X-ray crystallography. All the prepared compounds were evaluated for their antibacterial activity against Gram-positive bacteria ( Staphylococcus aureus , Bacillus subtilis , Clostridium sporogenes ), Gram-negative bacteria ( Pseudomonas aeruginosa , Escherichia coli ), and antifungal activity against Aspergillus fumigatus , Penicillium chrysogenum , Fusarium oxysporum , Candida albicans. The synthesized compounds displayed interesting antimicrobial activity. Compounds 4 and 12 were the most potent in this study and displayed higher activity compared to the reference drugs, with MIC value of 3.9–31.3 μg/mL against a panel of Gram-positive, Gram-negative bacteria and fungi. Molecular modeling was performed inside the active site of dihydropteroate synthase. The synthesized compounds showed similar orientation and binding interactions to that of the co-crystallized ligand inside the binding pocket.