title: Antimicrobial activity of rhodanine-3-acetic acid derivatives.
abstract: Twenty-four 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic acid (rhodanine-3-acetic acid)-based amides, esters and 5-arylalkylidene derivatives were synthesized, characterized and evaluated as potential antimicrobial agents against a panel of bacteria, mycobacteria and fungi. All of the derivatives were active against mycobacteria. N-(4-Chlorophenyl)-2-[5-(2-hydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]acetamide demonstrated the highest activity against Mycobacterium tuberculosis with minimum inhibitory concentrations (MIC) of 8-16μM. Non-tuberculous mycobacteria were the most susceptible to 2-[5-(2-hydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]acetic acids (MIC values ⩾32μM). The highest antibacterial activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus exhibited 4-(trifluoromethyl)phenyl 2-(4-oxo-2-thioxothiazolidin-3-yl)acetate (MIC⩾15.62μM). Several structure-activity relationships were identified. The activity against Gram-negative and fungal pathogens was marginal.
authors.affiliation: Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy, Charles University in Prague, Heyrovského 1203, 50005 Hradec Králové, Czech Republic. Electronic address: martin.kratky@faf.cuni.cz.
authors.forename: Martin
authors.initials: M
authors.lastname: Krátký
authors.affiliation: Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy, Charles University in Prague, Heyrovského 1203, 50005 Hradec Králové, Czech Republic.
authors.forename: Jarmila
authors.initials: J
authors.lastname: Vinšová
authors.affiliation: Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské námĕstí 7, 702 00 Ostrava, Czech Republic.
authors.forename: Jiřina
authors.initials: J
authors.lastname: Stolaříková
mesh_terms: D019342:Acetic Acid / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D006094:Gram-Positive Bacteria / Q000187:drug effects; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D066244:Proton Magnetic Resonance Spectroscopy; D012236:Rhodanine / Q000737:chemistry / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared
chemical_list: D000890:Anti-Infective Agents; D012236:Rhodanine; D019342:Acetic Acid
keywords: 2-(4-Oxo-2-thioxothiazolidin-3-yl)acetic acid; Amides; Antibacterial activity; Antifungal activity; Antimycobacterial activity; Condensation; Esters; In vitro activity; Rhodanine