Synthesis, Characterization, Antimicrobial and Molecular Docking Study of Benzooxadiazole Derivatives

Abstract

In this study, a series of new1,2,5-oxadiazole compounds derived from 4-chloro-7-nitro-benzo 1,2,5-oxadiazole was synthesized using different organic procedures. The resulting derivatives were chemically characterized and their structures were confirmed by FT-IR and NMR analysis. All the compounds were also evaluated for their antibacterial and antifungal activity against four types of pathogenic bacteria: S.aureus, S.epidermidis (as gram-negative bacteria), E.coli, Klebsiella spp. (as gram-positive bacteria) and the fungus Candida albicans using the agar well diffusion method. The synthesized oxadiazole derivatives exhibited significant antibacterial and moderate antifungal activities. Exploring the binding between the potent synthesized derivative 8 within the active site of glucosamine-6-phosphate synthase, the target enzyme for the antimicrobial agents was achieved using Autodock 4.2 package. The interaction modes of the generated conformers inside the binding pocket were found to enhance the in vitro results, and strongly recommended the new derivatives as promising antimicrobial agents.

Synthesis of Some Azo Dyes Based on 2,3,3-Trimethyl-3H-indolenine

“…The -N=N-chromophore group, as the electron-withdrawing group is principally responsible for the color observed. [23][24][25][26][27][28][29][30] The synthesis of azo dyes is distinguished by their simplicity, which takes place in acid and alkaline conditions, with the interaction of weak electrophiles (aryl diazonium ion) and strong nucleophiles (activated aromatic compound). The first stage involves N-nitrosation (diazotization) of aromatic amines to diazonium salt in a mineral acid area at low temperature, and the second stage takes place by coupling the diazonium ion to an electron-rich aromatic ring via an electrophilic aromatic substitution reaction.…”

“…After the coupling reaction, the azo group bonded to the nucleophiles and yielded a desired colored product. [23][24][25][26][27][28][29][30] In this study, we used three different pathways to synthesize new azo compounds (Scheme 1), including the classical way of syntheses, such as diazotization of amine at low temperature and subsequent coupling of the resulting diazo salt with a coupler, also, reducing the nitro compound by boiling in Zn dust in an alkaline solution, and by heating the amine with MnO 2 in toluene. [31][32][33][34] Scheme 1.…”