Antimicrobial activity of quinoxaline 1,4-dioxide with 2- and 3-substituted derivatives

Abstract

Quinoxaline is a chemical compound that presents a structure that is similar to quinolone antibiotics. The present work reports the study of the antimicrobial activity of quinoxaline N,N-dioxide and some derivatives against bacterial and yeast strains. The compounds studied were quinoxaline-1,4-dioxide (QNX), 2-methylquinoxaline-1,4-dioxide (2MQNX), 2-methyl-3-benzoylquinoxaline-1,4-dioxide (2M3BenzoylQNX), 2-methyl-3-benzylquinoxaline-1,4-dioxide (2M3BQNX), 2-amino-3-cyanoquinoxaline-1,4-dioxide (2A3CQNX), 3-methyl-2-quinoxalinecarboxamide-1,4-dioxide (3M2QNXC), 2-hydroxyphenazine-N,N-dioxide (2HF) and 3-methyl-N-(2-methylphenyl)quinoxalinecarboxamide-1,4-dioxide (3MN(2MF)QNXC). The prokaryotic strains used were Staphylococcus aureus ATCC 6538, S. aureus ATCC 6538P, S. aureus ATCC 29213, Escherichia coli ATCC 25922, E. coli S3R9, E. coli S3R22, E. coli TEM-1 CTX-M9, E. coli TEM-1, E. coli AmpC Mox-2, E. coli CTX-M2 e E. coli CTX-M9. The Candida albicans ATCC 10231 and Saccharomyces cerevisiae PYCC 4072 were used as eukaryotic strains. For the compounds that presented activity using the disk diffusion method, the minimum inhibitory concentration (MIC) was determined. The alterations of cellular viability were evaluated in a time-course assay. Death curves for bacteria and growth curves for S. cerevisiae PYCC 4072 were also accessed. The results obtained suggest potential new drugs for antimicrobial activity chemotherapy since the MIC's determined present low values and cellular viability tests show the complete elimination of the bacterial strain. Also, the cellular viability tests for the eukaryotic model, S. cerevisiae, indicate low toxicity for the compounds tested.

Synthesis and Antibacterial Activity of Ionic Liquids and Organic Salts Based on Penicillin G and Amoxicillin hydrolysate Derivatives against Resistant Bacteria

“…Bacterial resistance to antibiotics has been increasing in Europe over the last few years [1][2][3]. New classes of antibiotics have not been introduced recently [4][5][6][7], and, thus, more resistances to old drugs are developing daily [8][9][10]. Recent efforts and huge investments being made in this field by big pharma companies such as GlaxoSmithKline, Merck, Pfizer and Wyeth [3][4][5]11,12] have had disappointing returns from their R&D departments, including clinical trials.…”

Antimicrobial Evaluation of New Quinoxaline Derivatives Synthesized by Selective Coupling with Alkyl Halides and Amino Acids Esters

“…The antimicrobial resistance is a serious threat to global public health, because of the widely disseminated and careless use of antimicrobials . Searching for new antimicrobials to overcome the emergence of antibiotic resistance is necessary nowadays.…”

Crystal structure and Hirshfeld surface analysis of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-methylquinoxalin-2(1H)-one

“…Diversely substituted quinoxalines and their derivatives embedded with variety of functional groups are important biological agents and a significant amount of research activity has been directed towards this class of compounds. These molecules exhibit a wide range of biological applications and are potentially useful in medicinal chemistry research and have therapeutic applications such as antimicrobial (Attia et al, 2013;Vieira et al, 2014;Teja et al, 2016), anti-inflammatory (Guirado et al, 2012), anticancer (Abbas et al, 2015), antidiabetic (Kulkarni et al, 2012) and antihistaminic activities (Sridevi et al, 2010). As a continuation of our research works on the synthesis, spectroscopic and biological properties of quinoxaline derivatives (Ramli et al, 2013(Ramli et al, , 2017Ramli & Essassi, 2015;Abad et al, 2018a,b,c;Ellouz et al, 2015;Sebbar et al, 2014), we report herein the molecular and crystal structures along with the Hirshfeld surface analysis of the title compound, 1-[(1-butyl-1H-1,2,3triazol-5-yl)methyl]-3-methyl-1,2-dihydroquinoxalin-2-one.…”