Synthesis and evaluation of the antimicrobial activities of 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-2-thioxothiazolidin-4-one derivatives

• Published in: European journal of medicinal chemistry Vol. 74; pp. 405 - 410
• Main Authors: Liu, Jia-Chun, Zheng, Chang-Ji, Wang, Meng-Xiao, Li, Ya-Ru, Ma, Long-xu, Hou, Shao-Pu, Piao, Hu-Ri
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 03.03.2014; Elsevier
• Subjects: 1,3,4-Oxadiazole; 2-Thioxothiazolidin-4-one; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Antibacterial activity; Chemistry, Medicinal; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Microbial Sensitivity Tests; Pharmacology & Pharmacy; Science & Technology; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Spectrophotometry, Infrared; Thiazolidines - chemical synthesis; Thiazolidines - pharmacology; 1,3,4-Oxadiazole; Antibacterial activity; 2-Thioxothiazolidin-4-one; METHICILLIN-RESISTANT; RHODANINE DERIVATIVES; ACID; ANTIBACTERIAL; INHIBITORS; RESISTANT STAPHYLOCOCCUS-AUREUS
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2013.12.054

Two novel series of 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-2-thioxothiazolidin-4-one derivatives were designed and synthesized, and their anti-bacterial activities evaluated. These compounds showed broad-spectrum inhibitory activities against both Gram-positive and Gram-negative bacteria with minimum inhibitory concentration (MIC) values in the range of 1–64 μg/mL. The activity of compound 6c was the more potent with MIC values of 1 μg/mL against the MRSA (3167 and 3506) strains than those of gatifloxacin, oxacillin, and norfloxacin. Compared to the previously reported rhodanine derivatives, 2-thioxothiazolidin-4-one derivatives exhibited an inhibition against Gram-negative strains due to the introduction of a 1,3,4-oxadiazole moiety, among which compounds 3 showed moderate activities against the Gram-negative bacteria (Escherichiacoli 1924) with MIC values of 16 μg/mL. [Display omitted] Two novel series of 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-2-thioxothiazolidin-4-one derivatives were designed, synthesized and evaluated for their anti-bacterial activity. •Two novel series of 2-thioxothiazolidin-4-one derivatives were synthesized.•Compounds 3a–k were potent against both Gram-positive and Gram-negative bacteria.•6c showed strongest antibacterial activity with the MIC value of 1 μg/mL.