Synthesis, antibacterial and antifungal activity of new 3-biphenyl-3H-Imidazo[1,2-a]azepin-1-ium bromides

Demchenko, S. A.; Lesyk, Roman; Zuegg, Johannes; Elliott, Alysha G.; Fedchenkova, Yu. A.; Suvorova, Z. S.; Demchenko, A. M.

doi:10.1016/j.ejmech.2020.112477

Cited by 10 publications

(3 citation statements)

References 16 publications

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“…They reported that the derivatives showed potent antibacterial activity which were comparable to standard drugs [ 22 ]. The antibacterial and antifungal properties of 3-biphenyl-3H-Imidazo[1,2-a]azepin-1-ium bromide derivatives have also been assessed, with some of the compounds showing broad activity against S. aureus, C. neoformans and C. albicans at minimum inhibitory concentrations ranging from 4 to 8 μg/mL [ 23 ]. Although the antibacterial activity of alkyl imidazoles have been reported [ 20 ], their ability to impact biofilm formation or QS-mediated processes have not been explored.…”

Section: Introductionmentioning

confidence: 99%

N-alkylimidazole derivatives as potential inhibitors of quorum sensing in Pseudomonas aeruginosa

Mensah

Boadu²,

Mensah³

et al. 2022

Heliyon

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Section: Introductionmentioning

confidence: 99%

N-alkylimidazole derivatives as potential inhibitors of quorum sensing in Pseudomonas aeruginosa

Mensah

Boadu²,

Mensah³

et al. 2022

Heliyon

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“…Moreover, earlier we established the antifungal activity of derivatives of 3-aryl-6,7-dihydro-5 H -pyrrolo[1,2- a ]imidazole derivatives, structurally related to heterocycles [ 17 ]. Thus, quaternary salt VI (3-biphenyl-4-yl-1-(4-ethylphenyl)-6,7,8,9-tetrahydro-5 H -imidazo[1,2- a ]azepin-1-ium bromide) showed a polyvalent activity to S. aureus , C. neoformans , and C. albicans approaching reference drugs in their activity [ 18 ]. Given the above arguments, the aim of this work was to design novel 5 H -pyrrolo[1,2- a ]imidazole and 5 H -imidazo[1,2- a ]azepine quaternary salts as potential antimicrobial agents ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts

et al. 2021

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A series of novel 3-aryl-5H-pyrrolo[1,2-a]imidazole and 5H-imidazo[1,2-a]azepine quaternary salts were synthesized in 58–85% yields via the reaction of 3-aryl-6, 7-dihydro-5H-pyrrolo[1,2-a]imidazoles or 3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines and various alkylating reagents. All compounds were characterized by 1H NMR, 13C NMR, and LC-MS. The conducted screening studies of the in vitro antimicrobial activity of the new quaternary salts derivatives established that 15 of the 18 newly synthesized compounds show antibacterial and antifungal activity. Synthesized 3-(3,4-dichlorohenyl)-1-[(4-phenoxyphenylcarbamoyl)-methyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-1-ium chloride 6c possessed a broad activity spectrum towards Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Cryptococcus neoformans, with a high hemolytic activity against human red blood cells and cytotoxicity against HEK-293. However, compound 6c is characterized by a low in vivo toxicity in mice (LD50 > 2000 mg/kg).

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“…Some of them display narrow spectrum of antimicrobial activity, unsatisfactory pharmacokinetic, high rate of side effects etc [3,4]. These facts are the reasons that medicine is in urgent need of novel antimicrobial substances [5,6] The core of 5H- [1,2,4]triazolo [4,3-a]azepine is a part of many compounds possessing analgesic, anxiolyt-ic, anti-inflammatory and antitumor activities Additionally, structurally close to them 3-biphenyl-3H-imidazo[1,2-a]azepin-1-ium bromides display antibacterial and antifungal activity [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of 3-arylaminomethyl-1-(2-oxo-2-arylethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a] azepin-1-ium bromides and aryl-(4-R1-phenyl-5,6,7,8-tetrahydro-2,2a,8a-triazacyclopenta[cd]azulen-1-ylmethyl)-amines

Demchenko¹,

Suvorova

Fedchenkova

et al. 2021

SR: PS

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The aim of this work is to develop methods of synthesis of 3-arylaminomethyl-1-(2-oxo-2-arylethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-1-ium bromides and aryl-(4-R1-phenyl-5,6,7,8-tetrahydro-2,2a,8a-triazacyclopenta[cd]azulen-1-ylmethyl)-amines and to study their antimicrobial activity against strains of gram-positive and gram-negative bacteria as well as yeast fungi. Materials and methods. 1Н NMR spectra were recorded on Bruker 400 spectrometer operating at frequency of 400 MHz. Antimicrobial activity of the compounds synthesized was evaluated by their minimum inhibitory concentration (MIC) values. Results and discussion. The interaction of 3-arylaminomethyl-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepines with substituted phenacyl bromides produced novel 3-arylaminomethyl-1-(2-oxo-2-arylethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-1-ium bromides. The latter when refluxed in 10 % solution of NaOH gave aryl-(4-R1-phenyl-5,6,7,8-tetrahydro-2,2a,8a-triazacyclopenta[cd]azulen-1-ylmethyl)-amines. The study of antimicrobial activity of the compounds obtained allowed to find derivatives which are active against С. albicans and S. aureus strains. Among the compounds tested 3-[(41-bromophenylamino)-methyl]-1-[2-(4-methoxyphenyl)-2-oxoethyl]-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-1-ium bromide 5cd appeared to be more active than the reference drug Cefixime and displayed close antimicrobial activity as the antibiotic Linezolid. Conclusions. It was found out that derivatives of 3-arylaminomethyl-1-(2-oxo-2-arylethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a]azepin-1-ium bromides display broad spectrum of antimicrobial activity and are able to inhibit growth of both bacteria and fungi. S. aureus and C. albicans turned out to be the most sensitive strains to the compounds tested, MIC was in the range of 6.2-25.0 mg/mL. Gram-negative strains of microorganisms were less sensitive to the compounds evaluated and 5fа was the most active derivative displaying antimicrobial activity at the concentration of 50.0 mg/mL. Antimicrobial activity of triazoloazepinium bromide derivatives was similar to that one of Linezolid and Fluconazole reference drugs and more pronounced than the activity of Cefixime. Hence, the data gathered evidence the feasibility of further study of the antimicrobial properties of the most active compounds in in vivo experiments aiming at assessment of the prospects for the creation of new effective and safe antimicrobial drugs based on them

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Synthesis, antibacterial and antifungal activity of new 3-biphenyl-3H-Imidazo[1,2-a]azepin-1-ium bromides

Cited by 10 publications

References 16 publications

N-alkylimidazole derivatives as potential inhibitors of quorum sensing in Pseudomonas aeruginosa

N-alkylimidazole derivatives as potential inhibitors of quorum sensing in Pseudomonas aeruginosa

Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts

Synthesis and antibacterial activity of 3-arylaminomethyl-1-(2-oxo-2-arylethyl)-6,7,8,9-tetrahydro-5H-[1,2,4]triazolo[4,3-a] azepin-1-ium bromides and aryl-(4-R1-phenyl-5,6,7,8-tetrahydro-2,2a,8a-triazacyclopenta[cd]azulen-1-ylmethyl)-amines

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