Synthesis and structure–activity relationship of novel 1,4-diazabicyclo[2.2.2]octane derivatives as potent antimicrobial agents

Yarinich, Lyubov A.; Буракова, Е. А.; Zakharov, Boris A.; Boldyreva, Elena V.; Бабкина, И. Н.; Tikunova, Nina; Silnikov, Vladimir N.

doi:10.1016/j.ejmech.2015.03.033

Cited by 20 publications

(12 citation statements)

References 38 publications

(57 reference statements)

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“…Other compounds with alkyl chains shorter or longer than 16 or 17 carbon atoms were less active. As with numerous types of sets of compounds possessing long alkyl chains [1,2,46,51,52,53], the socalled cut-off effect [54] was observed. The Gram-negative bacteria E. coli was the strain most sensitive to compound 12.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

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Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Lukáč

Devı́nsky

Pisárčik

et al. 2016

J Surfact & Detergents

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A series of novel phospholium amphiphilic compounds with straight alkyl chains with different numbers of carbon atoms (12,14,15,16,17,18) were synthesized. The quaternary phosphorus, phosphonium cation, is incorporated into a five-membered heterocyclic ring. Their physicochemical properties were investigated by measurements of surface tension, conductivity and dynamic light scattering. The critical micelle concentration (c M ), the surface tension value at the c M (c cmc ), the surface area at the surface saturation per head group (A cmc ), the ionization degree of micelle (a), the free energy of micellization (DG°m ic ), and hydrodynamic diameter (d h ) were determined. Antimicrobial activity was tested against bacteria and yeast. The structure-activity relationship was determined. 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.2 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6(0), 29.6(4), 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.6 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.9 (d, 1 J CP = 83.9 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.6 (d, 2 J CP = 10.7 Hz, Ph C ortho ), 134.6 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.4 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -H NMR (CDCl 3 , TMS) d: 0.88 (t, 3 J H,H = 6.7 Hz, 3H, CH 3 of alkyl chain), 1.13-1.38 (m, 22H, 11 9 CH 2 of alkyl chain), 1.38-1.62 (m, 4H, b, c CH 2 of alkyl chain) 2.29 (s, 6H, 2 9 = C-CH 3 ), 3.08-3.22 (m, 2H, a CH 2 of alkyl chain), 7.08 (d, 2 J HP = 30.9 Hz, 2H, = CHP), 7.54-7.61 (m, 2H, Ph H meta ), 7.61-7.75 (m, 1H, Ph H para ), 8.15-8.23 (m, 2H, Ph H ortho ); 13 C NMR (CDCl 3 , TMS) d: 14.1 (CH 3 of alkyl chain), 18.5 (d, 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.1 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6, 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.4 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.8 (d, 1 J CP = 83.8 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.5 (d, 2 J CP = 10.4 Hz, Ph C ortho ), 134.7 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.5 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -

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Section: Antimicrobial Activitymentioning

confidence: 99%

“…Cationic surfactants have long been studied for their antimicrobial effect. They possess antimicrobial activities against bacteria [1][2][3], yeast [1,4,5], fungi [6] and protozoa [7,8]. The most studied cationic surfactants are quaternary ammonium compounds (QACs) which also have interesting physicochemical properties.…”

Section: Introductionmentioning

confidence: 99%

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Lukáč

Devı́nsky

Pisárčik

et al. 2016

J Surfact & Detergents

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“…Synthetic amphiphilic polycationic compounds based on quaternary salts of 1,4diazabicyclo [2.2.2] octane (DABCO) possess a similar spectrum of biological activity and they can serve as a basis for new antibacterial drugs that are an alternative to modern antibiotics [8][9].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial activity of cationic amphiphil conjugates with ciprofloxacin

Zadvornykh

Zhang²,

Liu³

et al. 2022

ijhs

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The aim: Design and synthesis of new compounds with antibacterial activity. Determination of the minimum inhibitory and minimum bactericidal concentration of conjugates of cationic amphiphiles based on quaternary salts of 1,4-diazabicyclo[2.2.2]octane with ciprofloxacin. Materials and methods: The article is dedicated to the synthesis and primary assessment of antibacterial activity in vitro of conjugates of cationic amphiphiles based on quaternary salts of 1,4-diazabicyclo[2.2.2]octane with ciprofloxacin against gram-negative and gram-positive microorganisms. Results: The present work provides hybrid structures which include the widely used antibiotic ciprofloxacin and tetra-cationic DABCO derivatives. The last ones previously showed a wide spectrum of antimicrobial activity as well as primary studies of their antibacterial activity against gram-positive and gram-negative microorganisms in vitro. There was a high in vitro antibacterial activity against gram-negative pathogens, moderate against Staphylococcus aureus and low against Enterococcus faecalis. Conclusions: A range of amphiphilic polycationic compounds based on quaternary salts of 1,4-diazabicyclo[2.2.2]octane (DABCO) was synthesized and their biological activity was studied. The compounds have demonstrated high antibacterial activity. We assume that they can serve as a basis for the development of new antibacterial drugs.

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“…In biology, they can be used in peptide coupling or as potent alkaline phosphatase inhibitors . They are also known in applications such as herbicidal and deterrent compounds , or as potent antimicrobial agents …”

Section: Introductionmentioning

confidence: 99%

“…59 They are also known in applications such as herbicidal and deterrent compounds 45,60 or as potent antimicrobial agents. 61 Herein, we would like to present the syntheses and characterization of a series of DABCO ILs with dicyanamide anion, substituted with alkyl chains with an even and odd number of carbon atoms ranging from C 2 to C 12 . All compounds were first synthesized as bromide quaternary ammonium intermediates.…”

Section: ■ Introductionmentioning

confidence: 99%

Mono N-Alkylated DABCO-Based Ionic Liquids and Their Application as Latent Curing Agents for Epoxy Resins

Zielinski

Szpecht

Hinc

et al. 2021

ACS Appl. Polym. Mater.

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Research on ionic liquids is constantly providing information on their new and more advanced applications. Undoubtedly, the use of latent curing agents for epoxy resins is one of the most interesting applications of this group of compounds. In this work, a detailed description of the synthesis and physicochemical studies of DABCO-based (1,4-diazabicylo[2.2.2]octane) ionic liquids is presented. Their most valuable feature is that they can be latent curing agents for polymerization of epoxy resins, which in turn can be used, when combined with fibers, as composites with special, new properties. The research includes detailed discussion of synthesis of new DABCO-ILs, focusing on obtaining pure compounds and expanding current knowledge on the subject. Thermal (DSC) and chromatographic (IC) properties have been discussed for all presented salts. Furthermore, ionic liquids with dicyanamide and triflate anion have demonstrated the ability to initiate polymerization of epoxy resins. Subsequently, all mixtures were cured into cubical shape and were subjected to the Shore hardness test (SHT). The main advantages of the obtained ILs are (i) the ability to store ionic liquids/epoxy resin mixture for prolonged periods of time without deterioration of curing properties and (ii) a significantly lower quantity of ionic liquids used in the process of curing epoxy resins.

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Synthesis and structure–activity relationship of novel 1,4-diazabicyclo[2.2.2]octane derivatives as potent antimicrobial agents

Cited by 20 publications

References 38 publications

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Antibacterial activity of cationic amphiphil conjugates with ciprofloxacin

Mono N-Alkylated DABCO-Based Ionic Liquids and Their Application as Latent Curing Agents for Epoxy Resins

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