Synthesis, Biological Evaluation and In Silico Studies of Oxime Ether Derivatives Containing a Quinoxaline Moiety

摘要

In this research, synthesis of O-oxime ethers containing amino cyclic residues was described. Oximation of aromatic ketones had been followed by an O-alkylation reaction with epichlorohydrin produce the corresponding O-oxime ether adducts. The cyclization of o-phenylendiamine with O-oxime ether adducts led to synthesis of new analogues of quinoxaline compounds. The in vitro antibacterial activities of all compounds were evaluated against Escherichia coli ATTC 35218 and Staphylococcus aureus ATCC 6538 standard strains and were compared to those of tetracycline and penicillin as reference drugs. Furthermore, molecular docking studies of synthetized compounds were implemented. The results of docking studies indicated that derivatives with small substitutions such as methyl and ethyl, exhibited the highest affinity and binding to the active site of tested bacteria (E. coli Mur B (PDB ID: 2Q85) and S. aureus Gyrase B (PDB ID: 3G75)) which led to the better biological effect of these compounds.