Synthesis, anti-mycobacterial, anti-trichomonas and anti-candida in vitro activities of 2-substituted-6,7-difluoro-3-methylquinoxaline 1,4-dioxides

Carta, Antonio; Loriga, Mario; Paglietti, Giuseppe; Mattana, Antonella; Fiori, Pier Luigi; Mollicotti, Paola; Sechi, Leonardo Antonio; Zanetti, Stefania Anna Lucia

doi:10.1016/j.ejmech.2003.11.008

Cited by 90 publications

(45 citation statements)

References 12 publications

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“…Quinoxaline ring system represents the building block of many biologically active compounds that possess antiinflammatory [1,2], antibacterial [3][4][5], antifungal [6], anticancer [7,8], antimalarial [9], CNS depressant [10] and hypoglycemic [11] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives

2011

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KEYWORDSNew derivatives of 3,4-dihydroquinoxaline-2(1H)-one were synthesized and characterized. Representative examples were evaluated for their antimicrobial and antifungal activities using Tetracycline and Nystatin as reference compound. One of the tested compounds 10a was found to exhibit slight activity against Staphylococcus aureus. Compounds 10b, 11b and 14b showed slight activity against Escherichia coli. Moreover, nineteen compounds were screened for their inhibition effect on CDK5, CK1, and GSK-3β. None of the tested compounds showed an inhibition activity below 10 µM concentration.Quinoxaline 3,4-dihydroquinoxalin Antimicrobial activity CK1 inhibitors CDK5 inhibitors GSK-3β inhibitors

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives

2011

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“…Over the last two decades, many papers have been published, in which both synthesis and biological activity assessment of a large number of QdNOs derivatives have been described [10,11]. Recent studies have demonstrated that QdNOs are endowed with antituberculosis [12,13], antiviral [14], antichagasic [15], anticandida [16] activities and property of hypoxic selectivity [17], depending on specific chemical features. The previous encouraging results prompted us to further analyze the biological activity of the animal-used QdNOs.…”

Section: Introductionmentioning

confidence: 99%

In vitro antimicrobial activities of animal-used quinoxaline 1,4-di-N-oxides against mycobacteria, mycoplasma and fungi

et al. 2016

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BackgroundThe quinoxaline 1,4-di-N-oxides (QdNOs) were known as potent antibacterial agents. For the purpose of evaluating the bioactivity of existing animal-used QdNOs drugs against representative pathogenic microorganism, the representative drugs of quinoxalines including cyadox, mequindox, quinocetone and their metabolites were submitted to the in vitro evaluation for antituberculosis, antimycoplasma, antifungal and antiviral activities.ResultsIn antituberculosis assays, the prototype compounds were active (MIC = 4 ~ 8 μg/mL) against Mycobacterium tuberculosis H37Rv and M. bovis. Combined antimicrobial susceptibility test indicated that cyadox, mequindox and quinocetone combined with rifampicin had additive effect against M. tuberculosis complex with Fractional Inhibitory Concentration Index (FIC) of 0.75. Results of antifungal assays showed that quinocetone was active against Microsporum canis with MIC of 8 μg/mL. Antimycoplasma screening showed a generally good activity of quinocetone against Mycoplasma gallisepticum and Mycoplasma hyopneumoniae, with MIC between 8 and 16 μg/mL. As shown from the combined antimicrobial susceptibility test, cyadox, mequindox and quinocetone combined with tetracycline had additive effect against Mycoplasma gallisepticum with FIC of 0.75. These compounds were also submitted to antiviral assay against infectious bursal disease virus, porcine reproductive and respiratory syndrome virus, porcine parvovirus and classical swine fever virus. The results obtained showed that these QdNOs and their metabolites have no inhibitory activity against these viruses in vitro.ConclusionsQdNOs exhibit antimicrobial activities against mycobacteria, mycoplasma and fungi. This study gives new insight in further application of QdNOs and offers a way to promote the healthcare of animal husbandry.Electronic supplementary materialThe online version of this article (doi:10.1186/s12917-016-0812-7) contains supplementary material, which is available to authorized users.

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“…Quinoxaline and quinoxaline 1,4-di- N -oxide are heterocycles that are often used in the synthesis of biologically active compounds [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31]. The former is described as a bioisoster of the quinoline, naphthyl, benzothienyl and other aromatic rings [32], and it can be found in the structure of anti-bacterial [1], anti-tuberculosis [5,6,7,9,10,11,13,14,16,22], anti-cancer [8,18,20,28], anti-malarial [12,24,26,29,30,31], anti-Chagas [15,25] and anti-inflammatory [19,27] drug candidates.…”

Section: Introductionmentioning

confidence: 99%

“…The former is described as a bioisoster of the quinoline, naphthyl, benzothienyl and other aromatic rings [32], and it can be found in the structure of anti-bacterial [1], anti-tuberculosis [5,6,7,9,10,11,13,14,16,22], anti-cancer [8,18,20,28], anti-malarial [12,24,26,29,30,31], anti-Chagas [15,25] and anti-inflammatory [19,27] drug candidates. The widespread activity of quinoxaline 1,4-di- N -oxides can be associated with the generation of free radicals [33].…”

Section: Introductionmentioning

confidence: 99%

Unexpected Reduction of Ethyl 3-Phenylquinoxaline-2- carboxylate 1,4-Di-N-oxide Derivatives by Amines

et al. 2008

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The unexpected tendency of amines and functionalized hydrazines to reduce ethyl 3-phenylquinoxaline-2-carboxylate 1,4-di-N-oxide (1) to afford a quinoxaline 1c and mono-oxide quinoxalines 1a and 1b is described. The experimental conditions were standardized to the use of two equivalents of amine in ethanol under reflux for two hours, with the aim of studying the distinct reductive profiles of the amines and the chemoselectivity of the process. With the exception of hydrazine hydrate, which reduced compound 1 to a 3-phenyl-2-quinoxalinecarbohydrazide derivative, the amines only acted as reducing agents.

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Synthesis, anti-mycobacterial, anti-trichomonas and anti-candida in vitro activities of 2-substituted-6,7-difluoro-3-methylquinoxaline 1,4-dioxides

Cited by 90 publications

References 12 publications

Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives

Synthesis of novel 3,4-dihydroquinoxalin-2(1H)-one derivatives

In vitro antimicrobial activities of animal-used quinoxaline 1,4-di-N-oxides against mycobacteria, mycoplasma and fungi

Unexpected Reduction of Ethyl 3-Phenylquinoxaline-2- carboxylate 1,4-Di-N-oxide Derivatives by Amines

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