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    Novel N-Heterocyclic Carbene Silver(I) Complexes: Synthesis, Structural Characterization, Antimicrobial and Cytotoxicity Potential Studies
    (Soc Brasileira Quimica, 2020) Slimani, Ichraf; Chakchouk-Mtibaa, Ahlem; Mellouli, Lotfi; Mansour, Lamjed; Ozdemir, Ismail; Gurbuz, Nevin; Hamdi, Naceur
    In this study, a series of unsymmetrical N,N-disubstituted benzimidazolium salts were synthesized as N-heterocyclic carbene (NHC) (2a-2j) and their Ag-I complexes. Their structures were characterized by elemental analyses, H-1 and C-13 nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy techniques. Further, both the salts and their silver(I)-NHC complexes have been evaluated for their potential antibacterial properties against a panel of bacterial strains namely, Micrococcus luteus, Listeria monocytogenes, Salmonella Typhimurium, Staphylococcus aureus and Pseudomonas aeruginosa. The results show that silver complexes are effective against Salmonella Typhimurium, Listeria monocytogenes, and Micrococcus luteus with moderate to high activity, and their minimum inhibitory concentrations ranging from 0.0034 to 1.26 mg mL(-1). In addition, the benzimidazoles salts 2a-2j and silver-NHC complexes 3a-3j were screened for their antitumor activity. Complex 3e exhibited the highest antitumor effect with half-maximal inhibitory concentration (IC50) value of 4.2 mu g mL(-1) against MCF-7.
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    A Palladium Catalyst System for the Efficient Cross-Coupling Reaction of Aryl Bromides and Chlorides with Phenylboronic Acid: Synthesis and Biological Activity Evaluation
    (Mdpi Ag, 2017) Lamia, Boubakri; Chakchouk-Mtibaa, Ahlem; Hallouma, Bilel; Mansour, Lamjed; Mellouli, Lotfi; Ozdemir, Ismail; Yasar, Sedat
    New benzimidazolium salts 1a-c and their palladium bis-N-heterocyclic carbene complexes 2a-c and palladium PEPPSI-type complexes 3a-c were designed, synthesized and structurally characterized by NMR (H-1 and C-13), IR, DART-TOF mass spectrometry and elemental analysis. Then these complexes 2-3 were employed in the Suzuki-Miyaura cross-coupling reaction of substituted arenes with phenylboronic acid under mild conditions in toluene and DMF/H2O (1/1) to afford functionalized biaryl derivatives in good to excellent yields. The antibacterial activity of palladium bis-N-heterocyclic carbene complexes 2a-c and palladium PEPPSI-type complexes 3a-c was measured by disc diffusion method against Gram positive and Gram negative bacteria. Compounds 2a, 2c and 3a-c exhibited potential antibacterial activity against four bacterial species among the five used indicator cells. The product 2b inhibits the growth of the all five tested microorganisms. Moreover, the antioxidant activity determination of these complexes 2-3, using 2.2-diphenyl-1-picrylhydrazyl (DPPH) as a reagent, showed that compounds 2a-c and 3b possess DPPH antiradical activity. The higher antioxidant activity was obtained from the product 2b which has radical scavenging activity comparable to that of the two used positive controls (gallic acid GA and tutylatedhydroxytoluene BHT). Investigation of the anti-acetylcholinesterase activity of the studied complexes showed that compounds 2b, 3a, and 3b exhibited moderate activity at 100 g/mL and product 2b is the most active.
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    Ruthenium(II) complexes bearing benzimidazole-based N-heterocyclic carbene (NHC) ligands as potential antimicrobial, antioxidant, enzyme inhibition, and antiproliferative agents
    (Taylor & Francis Ltd, 2022) Boubakri, Lamia; Chakchouk-Mtiba, Ahlem; Naouali, Olfa; Mellouli, Lotfi; Mansour, Lamjed; Ozdemir, Ismail; Yaser, Sedat
    In this work, new substituted benzimidazolium salts 2a-d having different groups on the side chain have been synthesized and reacted with Ag2O to produce Ag(I) N-heterocyclic carbene (NHC) complexes 3a-d. Ag(I)-NHC complexes were used as a carben transfer agents to synthesize ruthenium(II)-NHC complexes 4a-d. The structures of all compounds were characterized by H-1 NMR, C-13 NMR and FT-IR spectroscopies and elemental analysis. The IC50 values of these complexes were determined by MTT assay against MCF7, MDA-MB-231 and HF cancer cell lines. The lowest MIC values were obtained for two complexes, 4b and 4d. The Ru(II)-NHC complexes generally triggered stronger bacterial growth inhibition than the metal-free benzimidazolium cations. Enzymatic inhibition investigation against acetylcholinesterase (AChE) and tyrosinase (TyrE) showed that 4b and 4d are the most potent inhibitors against AchE with an IC50 of 2.52 and 5.06 mu g mL(-1), respectively, and against TyrE with an IC50 of 19.88 and 24.95 mu g mL(-1), respectively. Antioxidant activity of the synthesized NHC ligands 2a-2d and their respective Ru(II)-NHC complexes 4a-4d was assessed by three different techniques: the 2.2-diphenyl-1-picrylhydrazyl (DPPH), the 2.2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radicals scavenging and the beta-carotene linoleic acid bleaching assay, showing that 4d has recorded an important antioxidant activity.