Reactions with 4-Thiohydantoin. Preparation of 5-Arylidene-4-Thiohydantoin, their Reactions towards Grignard Reagents and the Alkylating Agents

Shalaby, A. F. A.; Daboun, H. A.; Boghdadi, S. S. M.

doi:10.1515/znb-1974-1-231

Cited by 22 publications

(3 citation statements)

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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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“…The compounds considered in this paper were prepared as the result of Knoevenagel condensation of the appropriate benzaldehydes with 2-thiohydantoin, according to the described procedure [22], methylation of thiohydantoin derivatives with methyl iodide and subsequent reaction with glycine according to the method developed in our group [23,24].…”

Section: Source Of the Compoundsmentioning

confidence: 99%

Charge-assisted N–H…Cl hydrogen bonds in the structures of 5-benzylidene-imidazol-4-one glycinate hydrochlorides

Karolak‐Wojciechowska

Kieć‐Kononowicz

Sieroń

2009

Journal of Molecular Structure

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“…Thus, pharmacological in vitro and in vivo test results were in accordance. The starting 2-thiohydantoins (7 and 17) were obtained as previously described or in analogy to the described procedure [26]. The new derivative was prepared described below.…”

Section: +5 Bicyclic Derivatives From Series Bbmentioning

confidence: 99%

Imidazo[2,1‐b]thiazoles, imidazo[2,1‐b]imidazoles and Pyrrolo[1,2‐c]imidazoles. synthesis, structure and evaluation of benzodiazepine receptor binding

Kieć‐Kononowicz

Handzlik

Łażewska

et al. 2002

Journal of Heterocyclic Chem

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As a continuation of our studies on bicyclic heterocycles with benzodiazepine receptor affinity, derivatives with a 5:5 bicyclic skeleton, namely imidazo[2,1‐b]thiazoles, imidazo[2,1‐b]imidazoles and pyrrolo[1,2‐c]imidazoles were prepared. The compounds possessed an aromatic substituent with different spatial arrangement and distance to the bicyclic skeleton. X‐ray structure analysis was performed for Z‐2‐(4‐chlorobenzylidene)‐5,5‐diphenyl‐2,3,5,6‐tetrahydroimidazo[2,1‐b]imidazoline‐3,6‐dione (6a) and 5‐amino‐6‐cyano‐7‐phenyl‐1‐oxo‐3‐thioxo‐2,3‐dihydro‐1H‐pyrrolo[1,2‐c]imidazole (20a). In contrast to the previously described arylideneimidazo[2,1‐b]thiazepinones the smaller heterocyclic ring systems investigated in this study were devoid of meaningful benzodiazepine receptor affinity as well as anti‐convulsant activity.

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Reactions with 4-Thiohydantoin. Preparation of 5-Arylidene-4-Thiohydantoin, their Reactions towards Grignard Reagents and the Alkylating Agents

Cited by 22 publications

References 0 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

Charge-assisted N–H…Cl hydrogen bonds in the structures of 5-benzylidene-imidazol-4-one glycinate hydrochlorides

Imidazo[2,1‐b]thiazoles, imidazo[2,1‐b]imidazoles and Pyrrolo[1,2‐c]imidazoles. synthesis, structure and evaluation of benzodiazepine receptor binding

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