title: Antimicrobial activity of sulfonamides containing 5-chloro-2-hydroxybenzaldehyde and 5-chloro-2-hydroxybenzoic acid scaffold.
abstract: A series of novel sulfonamides containing 5-chloro-2-hydroxybenzaldehyde or 5-chloro-2-hydroxybenzoic acid scaffolds were designed, synthesized and characterized by IR, (1)H NMR and (13)C NMR. All ten target synthesized derivatives and starting sulfonamides were evaluated in vitro for the activity against Gram-positive and Gram-negative bacteria, fungi, Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium kansasii. The most active compound against methicillin-sensitive and methicillin-resistant Staphyloccoccus aureus was 5-chloro-N-{4-[N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl}-2-hydroxybenzamide with MIC 15.62-31.25 μmol/L. 4-Amino-N-(thiazol-2-yl)benzenesulfonamide and 4-(5-chloro-2-hydroxybenzylideneamino)-N-(thiazol-2-yl)benzenesulfonamide have shown the best activity against M. kansasii at the concentrations of 1-4 μmol/L. The efficacy against other strains was weaker and the studied derivatives exhibited almost none antifungal potency.
authors.affiliation: Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic.
authors.forename: Martin
authors.initials: M
authors.lastname: Krátký
authors.forename: Jarmila
authors.initials: J
authors.lastname: Vinšová
authors.forename: Marie
authors.initials: M
authors.lastname: Volková
authors.forename: Vladimír
authors.initials: V
authors.lastname: Buchta
authors.forename: František
authors.initials: F
authors.lastname: Trejtnar
authors.forename: Jiřina
authors.initials: J
authors.lastname: Stolaříková
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D001549:Benzamides / Q000138:chemical synthesis / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D000096926:Benzenesulfonamides
chemical_list: D000890:Anti-Infective Agents; D001549:Benzamides; D013449:Sulfonamides; D013844:Thiazoles; C573642:4-(5-chloro-2-hydroxybenzylideneamino)-N-(thiazol-2-yl)benzenesulfonamide; D000096926:Benzenesulfonamides; C573641:4-amino-N-(thiazol-2-yl)benzenesulfonamide; C573640:5-chloro-N-(4-(N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl)phenyl)-2-hydroxybenzamide