Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Bahnous, Mebarek; Bouraiou, Abdelmalek; Chelghoum, Meryem; Bouacida, Sofiane; Roisnel, Thierry; Smati, F; Bentchouala, Chafia; Gros, P.; Belfaitah, Ali

doi:10.1016/j.bmcl.2013.01.004

Cited by 35 publications

(9 citation statements)

References 27 publications

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“…2,4,6-Trinitrophenyl-N-methyl-nitramine (tetryl) was obtained following the method [21]. The N-containing heterocyclic nitrocompounds 3,6-dinitro-9H-carbazole (DNC), 1,3,6,8-tetranitro-9H-carbazole (TNC), 4,5,6-trinitrobenzimidazol-2-one (TriNBO) and 4,5,6,7-tetranitrobenzimidazol-2-one (TNBO) were synthesized according to methods [22][23][24][25], 3-nitro-1,2,4-triazole and 4(5)-nitroimidazole compounds were obtained as described in [26][27]. Their purities and structures were verified by means of the melting points, and TLC, NMR and IR analysis.…”

Section: Methodsmentioning

confidence: 99%

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

Šarlauskas¹,

Polmickaitė-Smirnova²,

Čėnas³

et al. 2019

chemija

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The antibacterial activity of a series of structurally diverse nitroaromatic compounds (NACs) (nitrobenzene and nitroheterocyclic derivatives) was estimated in terms of the minimum inhibitory concentrations (MICs) against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli bacteria strains in vitro. The resultant log of 1/MICs (pMICs) was subjected to a quantitative structure–activity relationship analysis (QSAR) using a set of molecular descriptors of the compounds assessed by means of quantum mechanical computation and other methods. The estimated pMIC values of NACs tentatively increased with an increase in their electrophilic potency (in terms of LUMO energy) along with the LUMO–HOMO energy gap (or chemical hardness) towards both bacteria strains. No reliable contribution of lipophilicity (octanol/water log P) of nitroaromatics was found to both bacteria strains. The activity of NACs towards S. aureus increased with an increase in their molecular weight and van der Waals volume, and it also tended to increase with an increase in their polar surface area (PSA) and in the number of hydrogen bond-acceptors (HBAs), whereas using these descriptors against E. coli strain, no satisfactory correlations were obtained. The activity of NACs towards both bacteria strains showed a parabolic type dependence upon the highest positive values of molecular electrostatic potentials (VS, max) that might partially be associated with the non-specific interaction of nitroaromatics with the surfaces of the negatively charged envelopes of bacteria at the initial stage of NACs’ action.

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Section: Methodsmentioning

confidence: 99%

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

Šarlauskas¹,

Polmickaitė-Smirnova²,

Čėnas³

et al. 2019

chemija

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“…It was proposed that the electrostatic interaction between the negatively charged bacterial cells and positively charged nanoparticles is essential for bactericidal efficiency of the nanoparticles [42,43]. Herein, the ZIF-8 NPs contain central Zn 2+ atom (having a positive charge) plus organic 2-methylimidazole ligands with known antibacterial activities [44] which are suitable for their interactions with the bacterial cell walls. Indeed, the antibacterial activities of Zn 2+ complexes containing imidazole ligands derivatives have been well established [45,46].…”

Section: Antibacterial Activitiesmentioning

confidence: 99%

Antibacterial electrospun chitosan-polyethylene oxide nanocomposite mats containing ZIF-8 nanoparticles

Kohsari

Shariatinia‬

Pourmortazavi

2016

International Journal of Biological Macromolecules

179

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“…Additionally, imidazoles are used in material science, catalysis, and the preparation of ionic liquids. Numerous methods for the synthesis of imidazoles have been designed, and several pertinent reviews have been published . Moreover, a photochemical one‐pot four‐component synthesis of tetrasubstituted imidazole derivatives has been reported .…”

Section: Introductionmentioning

confidence: 99%

Piperidinium Hydrogen Sulfate (PHS) as an Efficient Ionic Liquid Catalyst for the Synthesis of Imidazole Derivative under Solvent‐Free Condition

Albayati

Marzouk

Abdelhamid

2019

Journal of Heterocyclic Chem

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Piperidinium hydrogen sulfate is used as a very important new catalyst for the synthesis of the biologically active compounds from a series of multi‐substituted imidazole components by the simple reaction of benzyl with different aromatic aldehydes, ammonium acetate, and phenethylamine or butylamine as amine derivatives. The key merits of this method are very shorter reaction times, excellent yield, and ease of stabilization. Furthermore, the produced products can be purified by a non‐chromatographic technique, and the catalyst is reusable. All of these new synthesized components have been characterized and checked from spectral data: IR, 1H‐NMR, and 13C‐NMR spectra and elemental analyses.

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Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Cited by 35 publications

References 27 publications

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

The QSAR study for antibacterial activity of structurally diverse nitroaromatics

Antibacterial electrospun chitosan-polyethylene oxide nanocomposite mats containing ZIF-8 nanoparticles

Piperidinium Hydrogen Sulfate (PHS) as an Efficient Ionic Liquid Catalyst for the Synthesis of Imidazole Derivative under Solvent‐Free Condition

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