Bis(Substituted Phenylamino)Glyoxime derivatives: Synthesis, characterization, and antimicrobial evaluation

Abstract

In present work, a set of bis(substituted phenylamino) glyoxime derivatives are presented by the drop-wise addition of corresponding primary aryl amines to the dichloroglyoxime (1). Reactions of correspond-ing primary aryl amines containing various substituents in different positions with dichloroglyoxime (1) gave thirteen compounds. The structural characterization of a set of bis(substituted phenylamino) gly-oxime derivatives have been performed on the basis of FTIR, mass, proton, and carbon NMR methods. The crystal structure of compound 3a has been determined by X-ray diffraction on a single crystal. The NMR spectrum and X-ray data of 3a show that two hydroxyl groups of dioxime situated at anti posi-tion. Furthermore, all of the synthesized compounds ( 3a-m ) were tested for in vitro both antimicrobial activity. The minimal inhibitory concentrations (MICs) against 7 bacteria and 3 yeasts were also deter-mined. Among them, compound 3f was the most potent compound against S. aureus with the value of MIC = 9.76 mu g/mL for the antibacterial activity, in addition to this, compound 3i has a good potency against S. aureus and C. tropicalis (MIC = 78.12 mu g/mL) for both antibacterial and antifungal activities, respectively. (C) 2021 Elsevier B.V. All rights reserved.