Received:August 18, 2020;   Published: September 03, 2020

DOI: 10.32474/AOICS.2020.04.000196

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Abstract

Three new 2,5-disubstituted 1,3,4-oxadiazole derivatives from dicarboxylic acids were synthesized in a three-step synthesis procedure that involved formation of esters and hydrazides as intermediates. The final products; 1,4-bis(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)benzene,1,4-bis(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)benzene and 1,2-bis(4-nitro-3-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)disulfane; which all have a C2 symmetry and contain two oxadiazole rings were obtained in yields of 45.3 to 50%. The oxadiazoles were successfully characterized using Infrared Spectroscopy, Proton and Carbon Nuclear Magnetic Resonance Spectroscopy; and Gas Chromatography-Mass Spectrometry. The three synthesized compounds were tested for antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Pseudomonas aeruginosa and Candida albicans. Only 1,2-bis(4-nitro-3-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)disulfane showed appreciable biological/ antimicrobial activity against these microorganisms with sensitivity zones of inhibition of 10 -19 mm, MIC of 0.37 - 1.11 mg/mL and MBC of 1.11 - 3.33 mg/mL at concentrations of 2.5 to 20 mg/mL. 

Keywords: Disubstituted oxadiazole; heterocyclic compounds;C₂ symmetry; antimicrobial activity

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Abstract| Introduction| Materials and Methods| Result and discussion| Conclusion| Conflicts of Interest| Acknowledgement| References|