Synthesis and Antimicrobial Activity of Bis-4,6-sulfonamidated 5,7-Dinitrobenzofuroxans

Irina V Galkina,Vladimir I Galkin,Marina P Shulaeva,Elena V Tudriy,Luiza M Usupova,Oskar K Pozdeev,Yuliya V Bakhtiyarova,Svetlana N Egorova

doi:10.1155/2014/367351

Abstract

A new series of bis-4,6-sulfonamidated 5,7-dinitrbenzofuroxans 7–11had been synthesized and tested for antimicrobial activity. The structures of new sulfanilamide derivatives were characterized by elemental analysis, IR spectroscopy, and mass spectrometry (MALDITOF). The synthesized compounds were tested for theirin vitroantimicrobial activity using the disk diffusion method against Gram-positive bacteriaStaphylococcus aureus; the Gram-negative bacteriaEscherichia coli, Pseudomonas aeruginosa, andProteus mirabilis; the fungal strainAspergillus niger; and the yeast-like pathogenic fungusCandida albicans. Our results indicate that the compounds7–11exhibit potent antimicrobial activity. The stability of the compounds was evaluated by TG and DSC methods.

Highlights

A need for new antimicrobial agents is justified as more microorganisms develop resistance to the present drugs available in the market
We present the synthesis and antimicrobial activity of a series of substituted 5,7-dichloro-4,6-dinitrobenzofuroxan 1 by sulfonamides 2–6, whose chemical structure has been confirmed by IR spectroscopy, mass spectrometry, and elemental analysis
Bacterial and fungal strains used in the antimicrobial evaluation were obtained from the Department of Microbiology (Museum of Culture Collections) of Kazan State Medical Academy, Russia, namely, Staphylococcus aureus (ATCC 29213), Escherichia coli (ATCC 25922), Pseudomonas aeruginosa (ATCC 27853), Proteus mirabilis (0fbb 12453), Aspergillus niger (ATCC 16620), and Candida albicans (ATCC 885-653)

Summary

Introduction

A need for new antimicrobial agents is justified as more microorganisms develop resistance to the present drugs available in the market. Sulfa drugs kill bacteria and fungi by interfering with cell metabolism They exert their effect by targeting the synthase dihydropteroate (DHPS) enzyme, which catalyzes folic acid pathway in bacteria and some eukaryotic cells [6] but is not present in human cells [4]. This is the basis for the selective effect of sulfonamides on bacteria and for their broad spectrum of antibacterial activity. Before penicillin G, these antimicrobials were standard therapies and are still in use today [7] The benzofuroxans and their chloro-nitro-substituted derivatives have been shown to exhibit a wide spectrum of biological activities [8] and the interest of medicinal chemists in them has grown over the last two decades. We present the synthesis and antimicrobial activity of a series of substituted 5,7-dichloro-4,6-dinitrobenzofuroxan 1 by sulfonamides 2–6, whose chemical structure has been confirmed by IR spectroscopy, mass spectrometry, and elemental analysis

Experimental

Results and Discussions

Conclusions