Antimicrobial activity of 5-arylidene aromatic derivatives of hydantoin. Part 2

Szymańska, Ewa; Kieć‐Kononowicz, Katarzyna; Białecka, Anna; Kasprowicz, A

doi:10.1016/s0014-827x(01)01172-7

Cited by 39 publications

(23 citation statements)

References 7 publications

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“…The synthesis and characteristics of compound BM-9 and its intermediates were described previously (19)(20)(21)(22)(23). Chemical procedures for and characteristics of BM-19, BM-27, BM-36, and BM-38 are presented in the supplemental material.…”

Section: Methodsmentioning

confidence: 99%

Novel Piperazine Arylideneimidazolones Inhibit the AcrAB-TolC Pump in Escherichia coli and Simultaneously Act as Fluorescent Membrane Probes in a Combined Real-Time Influx and Efflux Assay

Bohnert

Schuster²,

Kern³

et al. 2016

Antimicrob Agents Chemother

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In this study, we tested five compounds belonging to a novel series of piperazine arylideneimidazolones for the ability to inhibit the AcrAB-TolC efflux pump. The biphenylmethylene derivative (BM-19) and the fluorenylmethylene derivative (BM-38) were found to possess the strongest efflux pump inhibitor (EPI) activities in the AcrAB-TolC-overproducing Escherichia coli strain 3-AG100, whereas BM-9, BM-27, and BM-36 had no activity at concentrations of up to 50 M in a Nile red efflux assay. MIC microdilution assays demonstrated that BM-19 at 1/4 MIC (intrinsic MIC, 200 M) was able to reduce the MICs of levofloxacin, oxacillin, linezolid, and clarithromycin 8-fold. BM-38 at 1/4 MIC (intrinsic MIC, 100 M) was able to reduce only the MICs of oxacillin and linezolid (2-fold). Both compounds markedly reduced the MIC of rifampin (BM-19, 32-fold; and BM-38, 4-fold), which is suggestive of permeabilization of the outer membrane as an additional mechanism of action. Nitrocefin hydrolysis assays demonstrated that in addition to their EPI activity, both compounds were in fact weak permeabilizers of the outer membrane. Moreover, it was found that BM-19, BM-27, BM-36, and BM-38 acted as near-infrared-emitting fluorescent membrane probes, which allowed for their use in a combined influx and efflux assay and thus for tracking of the transport of an EPI across the outer membrane by an efflux pump in real time. The EPIs BM-38 and BM-19 displayed the most rapid influx of all compounds, whereas BM-27, which did not act as an EPI, showed the slowest influx.

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Section: Methodsmentioning

confidence: 99%

Novel Piperazine Arylideneimidazolones Inhibit the AcrAB-TolC Pump in Escherichia coli and Simultaneously Act as Fluorescent Membrane Probes in a Combined Real-Time Influx and Efflux Assay

Bohnert

Schuster²,

Kern³

et al. 2016

Antimicrob Agents Chemother

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“…Our previous studies were focused on various chemical modifications of hydantoin to give new GPCR-agents [13e15], compounds with antiarrhythmic-and/or anticonvulsant activity [16e19] as well as antibacterial agents with some syndrome to inhibit drug resistance in mycobacterial cells [20,21]. Based on interesting structures and pharmacological properties of the 5-aromatic-hydantoin derivatives, we decided to test this chemical group for their potency to combat MDR.…”

Section: Introductionmentioning

confidence: 99%

Amine–alkyl derivatives of hydantoin: New tool to combat resistant bacteria

Handzlik

Szymańska

Chevalier

et al. 2011

European Journal of Medicinal Chemistry

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a b s t r a c t A series of new 5,5-diphenylhydantoin derivatives with various amineealkyl terminal fragments at N1-position were synthesized. Then a series of twenty-eight compounds with the same hydantoin scaffold were evaluated for their potency to combat bacterial MultiDrug Resistance (MDR). Intrinsic antibacterial activities were first evaluated. As these compounds showed no direct activity on bacteria, their influence on minimal inhibitory concentration (MIC) of nalidixic acid was tested in two strains of Enterobacter aerogenes: the reference-strain ATCC-13048 and the CM-64 strain which over-produces AcrAB-TolC efflux pump. The compounds showed moderate-or low-anti-MDR properties. According to SAR-studies, hit compounds containing 2-methoxyphenylpiperazine at N1-terminal fragment and methylcarboxyl acid one at N3-position of hydantoin have been identified for further microbiological studies and pharmacomodulations to develop efflux pump inhibitors.

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“…Therefore, there has been great demand for highly efficient synthetic methods for the introduction of arylidene carbon-carbon double bond at the 5-position of the hydantoin or thiohydantoin ring [1,2]. So far, several typical synthetic strategies of 5-arylidene derivatives of hydantoin and thiohydantoin have been reported, including a traditional base-catalyzed aldol condensation of hydantoin and thiohydantoin with substituted benzaldehydes [1,3,5,6,9], improved aldol condensation such as one-pot multicomponent reaction of substituted benzaldehydes, glycine and potassium thiocyanate [10], microwave-assisted condensation of thiohydantoin/hydantoin with substituted benzaldehyde Schiff bases [11], Wittig-Horner Reaction [12–14], and Mn-catalyzed reactions of terminal alkynes with isocyanates [15]. Herein, we report a new protocol via sequential sulfonylation/desulfination to construct the 5-arylidene thiohydantoin.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of 5-Arylidene Thiohydantoin by Sequential Sulfonylation/Desulfination Reaction

Han

Dong

et al. 2013

IJMS

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The sequential sulfonylation/desulfination reactions of 5-benzylthiohydantoin with excess arylsulfonyl chlorides in the presence of triethylamine have been developed to afford a wide range of 5-arylidene thiohydantoin derivatives in moderate to excellent yields. A plausible sulfonylation/desulfination mechanism was proposed. The bioassay showed that these compounds exhibit certain fungicidal activities with the 71.9% inhibition rate of 2K against B. cinerea, and 57.6% inhibition rate of 2m against A. solani, respectively.

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Antimicrobial activity of 5-arylidene aromatic derivatives of hydantoin. Part 2

Cited by 39 publications

References 7 publications

Novel Piperazine Arylideneimidazolones Inhibit the AcrAB-TolC Pump in Escherichia coli and Simultaneously Act as Fluorescent Membrane Probes in a Combined Real-Time Influx and Efflux Assay

Novel Piperazine Arylideneimidazolones Inhibit the AcrAB-TolC Pump in Escherichia coli and Simultaneously Act as Fluorescent Membrane Probes in a Combined Real-Time Influx and Efflux Assay

Amine–alkyl derivatives of hydantoin: New tool to combat resistant bacteria

Facile Synthesis of 5-Arylidene Thiohydantoin by Sequential Sulfonylation/Desulfination Reaction

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