Synthesis and evaluation of the antimicrobial activities of 3-((5-phenyl-1,3,4-oxadiazol-2-yl)methyl)-2-thioxothiazolidin-4-one derivatives.
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.
Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University, College of Pharmacy, Yanji, Jilin Province 133002, PR China.
Jia-Chun
JC
Liu
Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University, College of Pharmacy, Yanji, Jilin Province 133002, PR China.
Chang-Ji
CJ
Zheng
Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University, College of Pharmacy, Yanji, Jilin Province 133002, PR China.
Meng-Xiao
MX
Wang
Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University, College of Pharmacy, Yanji, Jilin Province 133002, PR China.
Ya-Ru
YR
Li
Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University, College of Pharmacy, Yanji, Jilin Province 133002, PR China.
Long-xu
LX
Ma
Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University, College of Pharmacy, Yanji, Jilin Province 133002, PR China.
Shao-Pu
SP
Hou
Key Laboratory of Natural Resources and Functional Molecules of the Changbai Mountain, Affiliated Ministry of Education, Yanbian University, College of Pharmacy, Yanji, Jilin Province 133002, PR China. Electronic address: piaohuri@yahoo.com.cn.
Hu-Ri
HR
Piao
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013055:Spectrophotometry, Infrared; D053778:Thiazolidines / Q000138:chemical synthesis* / Q000494:pharmacology*
D000890:Anti-Infective Agents; D053778:Thiazolidines
1,3,4-Oxadiazole; 2-Thioxothiazolidin-4-one; Antibacterial activity