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 dropwise addition of corresponding primary aryl amines to the dichloroglyoxime (1). Reactions of corresponding 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) glyoxime 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 position. 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 determined. Among them, compound 3f was the most potent compound against S. aureus with the value of MIC = 9.76 μg/mL for the antibacterial activity, in addition to this, compound 3i has a good potency against S. aureus and C. tropicalis (MIC = 78.12 μg/mL) for both antibacterial and antifungal activities, respectively.