Antimicrobial activity of rhodanine-3-acetic acid derivatives

作者：Kratky Martin^*; Vinsova Jarmila; Stolarikova Jirina

来源：Bioorganic & Medicinal Chemistry, 2017, 25(6): 1839-1845.

DOI：10.1016/j.bmc.2017.01.045

• Amides
• Antibacterial activity
• Antifungal activity
• Antimycobacterial activity
• Condensation
• Esters
• In vitro activity
• 2-(4-Oxo-2-thioxothiazolidin-3-yl)acetic
• acid
• Rhodanine

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 8-16 mu M. Non-tuberculous mycobacteria were the most susceptible to 2-[5-(2-hydroxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl]acetic acids (MIC values >= 32 mu M). 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 >= 15.62 mu M). Several structure-activity relationships were identified. The activity against Gram-negative and fungal pathogens was marginal.

• 出版日期2017-3-15