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标题：Synthesis, characterization, and antimicrobial evaluation of novel 1,2,4-oxadiazoles derived from trans-3,4-(methylenedioxy)-cinnamic acid
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作者：João Rufino de Freitas Filho ; Clécio Souza Ramos ; Leonardo Alexandre Barros Bezerra 等
期刊名称：Acta Brasiliensis
印刷版ISSN：2526-432X
电子版ISSN：2526-4338
出版年度：2022
卷号：6
期号：1
页码：6-13
DOI：10.22571/2526-4338555
语种：English
出版社：Universidade Federal de Campina Grande
摘要：Compounds containing heterocyclic ring systems are of great importance both medicinally and industrially. Five-membered 1,2,4-oxadiazole heterocycles have received considerable attention because of their unique bioisosteric properties and unusual wide spectrum of biological activities. In this study, a series of 2-(3-aryl-1,2,4-oxadiazol-5-yl)-trans-3,4-(methylenedioxy)-cinnamyl derivatives was synthesized and characterized, andin vitroexperimental models were used to evaluate their antimicrobial activity. Synthesis, which involved microwave irradiation for 5 min, provided moderate yields of 1,2,4-oxadiazole (34–50%). Infrared (IR) andnuclear magnetic resonance (1H NMR and13C NMR) spectroscopy were used to determine the structures of 1,2,4-oxadiazole. The disk diffusion method was used to test the antibacterial activity of the novel 1,2,4-oxadiazole derivatives against Gram-positive (Staphylococcus aureus,Enterococcus faecalis,and Bacillus subtilis) and Gram-negative (Escherichia coli andKlebsiella pneumoniae) bacteria. The derivatives, 2-(3-m-toluyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl and 2-(3-pyrimidyl-1,2,4-oxadiazol-5-yl)-3,4-(methylenedioxy)-cinnamyl exhibited a minimum inhibitory concentration (MIC) of 19.5 μg mL−1againstS. aureus, and is four-fold more potent than the standard metronidazole (MIC =78 μg mL−1).