Fluoroquinolones: Synthesis and Application

Charushin, Valery N.; Носова, Э. В.; Lipunova, G. N.; Чупахин, О. Н.

doi:10.1007/978-3-319-04435-4_3

Cited by 19 publications

(13 citation statements)

References 209 publications

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“…Naphthyridines and their derivatives are known precursors of antibiotics, such as fluoroquinolones and quinolones [ 61 , 62 , 64 , 100 ]. The efflux pump inhibitory capacity of these substances is favored by their high binding affinity to these proteins, as verified for 2,3,4-trifluoro-N-(5-chloro-1,8-naphthyridin-2-yl)-benzenesulfonamide (Naph 3), which showed favorable interaction with NorA and MepA proteins in silico [ 101 ].…”

Section: Resultsmentioning

confidence: 99%

Efflux Pump (QacA, QacB, and QacC) and β-Lactamase Inhibitors? An Evaluation of 1,8-Naphthyridines against Staphylococcus aureus Strains

et al. 2023

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The bacterial species Staphylococcus aureus presents a variety of resistance mechanisms, among which the expression of β-lactamases and efflux pumps stand out for providing a significant degree of resistance to clinically relevant antibiotics. The 1,8-naphthyridines are nitrogen heterocycles with a broad spectrum of biological activities and, as such, are promising research targets. However, the potential roles of these compounds on bacterial resistance management remain to be better investigated. Therefore, the present study evaluated the antibacterial activity of 1,8-naphthyridine sulfonamides, addressing their ability to act as inhibitors of β-lactamases and efflux pump (QacA/B and QacC) against the strains SA-K4414 and SA-K4100 of S. aureus. All substances were prepared at an initial concentration of 1024 μg/mL, and their minimum inhibitory concentrations (MIC) were determined by the broth microdilution method. Subsequently, their effects on β-lactamase- and efflux pump-mediated antibiotic resistance was evaluated from the reduction of the MIC of ethidium bromide (EtBr) and β-lactam antibiotics, respectively. The 1,8-naphthyridines did not present direct antibacterial activity against the strains SA-K4414 and SA-K4100 of S. aureus. On the other hand, when associated with antibiotics against both strains, the compounds reduced the MIC of EtBr and β-lactam antibiotics, suggesting that they may act by inhibiting β-lactamases and efflux pumps such as QacC and QacA/B. However, further research is required to elucidate the molecular mechanisms underlying these observed effects.

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Section: Resultsmentioning

confidence: 99%

Efflux Pump (QacA, QacB, and QacC) and β-Lactamase Inhibitors? An Evaluation of 1,8-Naphthyridines against Staphylococcus aureus Strains

et al. 2023

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Section: Fluorine-containing Pharmaceuticals Withdrawn From the Marketmentioning

confidence: 99%

“…From there, a simple condensation reaction and treatment with polyphosphoric acid (PPA) lead to fluoroquinolone derivative 152 . On the other hand, the use of fluorine-containing benzoyl derivatives 153 , followed by cyclization of intermediates 154 , comprises another method for the synthesis of fluoroquinolone derivatives (Scheme , Method B ) …”

Section: Fluorine-containing Pharmaceuticals Withdrawn From the Marketmentioning

confidence: 99%

“…On the other hand, the use of fluorine-containing benzoyl derivatives 153, followed by cyclization of intermediates 154, comprises another method for the synthesis of fluoroquinolone derivatives (Scheme 57, Method B). 268 It has been widely reported that the presence of a fluorine atom in the C-6 position enhances antibacterial activity, potentially because of improved cell penetration of the fluorinated derivatives due to their increased lipophilicity. 188 This substitution has therefore allowed the development of new inhibitors of DNA gyrase, an essential enzyme which controls bacterial DNA replication.…”

Section: Fluorine-containing Pharmaceuticals Withdrawn From the Marketmentioning

confidence: 99%

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Chemical Aspects of Human and Environmental Overload with Fluorine

et al. 2021

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Over the last 100–120 years, due to the ever-increasing importance of fluorine-containing compounds in modern technology and daily life, the explosive development of the fluorochemical industry led to an enormous increase of emission of fluoride ions into the biosphere. This made it more and more important to understand the biological activities, metabolism, degradation, and possible environmental hazards of such substances. This comprehensive and critical review focuses on the effects of fluoride ions and organofluorine compounds (mainly pharmaceuticals and agrochemicals) on human health and the environment. To give a better overview, various connected topics are also discussed: reasons and trends of the advance of fluorine-containing pharmaceuticals and agrochemicals, metabolism of fluorinated drugs, withdrawn fluorinated drugs, natural sources of organic and inorganic fluorine compounds in the environment (including the biosphere), sources of fluoride intake, and finally biomarkers of fluoride exposure.

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“…The US Center for Disease Control and Prevention (CDC) has classified "high priority antibioticresistant bacteria" that include Mycobacterium tuberculosis (MDR, XDR), Neisseria gonorrhoeae, It is known that fluorine-containing heterocycles, especially fluoroquinolones, have gained attention as effective antibacterial agents. [15][16][17][18][19] We have recently elucidated how a fluorine atom (or CF3-group), incorporating at various positions a 5-(fluoroaryl) substituent in 4-(hetero)arylpyrimidines can affect their antibacterial activity against Mycobacterium tuberculosis and other pathogenic strains such as M. avium and M. terrae. 20 In this communication we report the synthesis of novel 6-fluoroaryl substituted [1,2,4]triazolo [1,5-a]pyrimidines using microwave-assisted Suzuki cross-coupling, and present data on their antimicrobial activities in vitro against Mycobacterium tuberculosis H37Rv and the gram-negative Neisseria gonorrhoeae ATCC 49226 bacteria.…”

Section: Introductionmentioning

confidence: 99%