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Öğe Bioactive NHC-derived palladium complexes: synthesis, catalytic activity for the Suzuki-Miyaura coupling of aryl chlorides and bromides and their antibacterial activities(Taylor & Francis Ltd, 2019) Boubakri, Lamia; Al-Ayed, Abdullah S.; Mansour, L.; Abutaha, Nael; Harrath, Abdel Halim; Ozdemir, I; Yasar, S.Pd(II)-bis(NHC) complexes (where NHC = N-heterocyclic carbene) bearing asymmetrically and symmetrically substituted NHC-ligand have been synthesized via deprotonation of 5,6-dimethylbenzimidazolium salts. The NHC precursors have been achieved via the two step N-alkylation of 5,6-dimethylbenzimidazole. The resultant salts were deprotonated with PdCl2 and K2CO3 in dry THF for 2(a-e). The obtained complexes were identified and characterized by H-1 and C-13 NMR, FT-IR, DART-TOF mass spectrometry and elemental analysis. These new Pd(II)-bis(NHC) complexes were applied as catalyst precursors for Suzuki-Miyaura cross-coupling reactions of aryl bromides and chlorides with phenylboronic acid to afford the corresponding products in good yields. This catalytic reaction was evaluated in the presence of KOtBu/toluene. The antibacterial activities of 2(a-e) were investigated against Gram (+)/(-) bacteria using the agar dilution procedure. The antibacterial activities of 2 vary with the nature of the ligands; MIC values of 2(a-e) were determined.Öğe Design, synthesis, and biological investigation of N-heterocyclic carbene-silver complexes for catalytic multicomponent coupling reactions(Pergamon-Elsevier Science Ltd, 2026) Guerfi, Samia; Berredjem, Yamina; Boubakri, Lamia; Zouaghi, Mohamed Oussama; Mansour, Lamjed; Gurbuz, Nevin; Ozdemir, IsmailBenzimidazolium silver salts 2a-f, bearing two nitrogen atoms substituted with different alkyl groups, were synthesized in high yields. These salts were readily converted into the corresponding N-heterocyclic carbene (NHC) silver(I) complexes 3a-f. The solution structures of these complexes were determined by mean of conventional spectroscopic methods (1H NMR, 13C{1H} NMR, FTIR) and their molecular structures optimized using density functional theory (DFT) at B3LYP level. Enzyme inhibition and antioxidant assays revealed that the biological activity of the new Ag-NHC complexes 3a-f strongly depend on the nature of the NHC substituents. Molecular docking confirmed high binding affinities toward AChE, with interactions taking place at both the peripheral and catalytic anionic sites, while ADMET analysis predicted favorable pharmacokinetic and toxicity profiles. Finally, a mild and efficient A(Y & imath;lmaz et al., 20243)-coupling protocol using 5,6-dimethylbenzimidazolebased NHC-silver(I) catalysts enabled the selective synthesis of propargyl amines.Öğe Novel nonsymmetrically benzimidazolium salts and their silver (I)-N-heterocyclic carbene complexes: Synthesis, DFT study and Anticancer activities(Elsevier, 2025) Rahali, Emna; Boubakri, Lamia; Gurbuz, Nevin; Ozdemir, Ismail; Mansour, Lamjed; Arfaoui, Youssef; Sauthier, MathieuA series of unsymmetrically substituted N-heterocyclic carbene (NHC) precursors were synthesized from the action of 5,6-dimethylbenzimidazole or benzimidazole with various alkyl halides in DMF at 80 degrees C for 72 h . These compounds were used to synthesize NHC-silver(I) complexes (3) by reacting these NHC precursors with Ag2O in DMC.The prepared compounds were structurally verified by several spectroscopic techniques including 1H NMR, 13C NMR, FT-IR, LC-MS, and C, H, N analysis. The structures of the NHC precursors and their corresponding silver(I) complexes were also investigated theoretically using density functional theory (DFT) at the BLYP/TZ2P level to optimize geometries and assess electronic properties via Voronoi Deformation Density (VDD) charge analysis. Additionally, the newly synthesized ligands and silver(I) complexes were evaluated for their in vitro anticancer activity against three human cancer cell lines including hepatocellular carcinoma (HePG2), lung adenocarcinoma (A549) and breast adenocarcinoma (MCF7). Most of the newly synthesized silver(I) complexes exhibited better activity than the ligands, and the results have been compared with Cisplatin as a reference drug.Öğe Preparation and characterization of PEPPSI-palladium N-heterocyclic carbene complexes using benzimidazolium salts catalyzed Suzuki-Miyaura cross coupling reaction and their antitumor and antimicrobial activities(Taylor & Francis Ltd, 2019) Boubakri, Lamia; Dridi, Khaireddine; Al-Ayed, Abdullah Sulaiman; Ozdemir, Ismail; Yasar, Sedat; Hamdi, NaceurNew palladium complexes were efficiently synthesized from the reaction of benzimidazolium salts 2a-e, potassium carbonate (K2CO3) and palladium chloride (PdCl2) in pyridine (for 3a-e). The catalytic activity of these complexes in a catalytic system including palladium complexes and K2CO3 in DMF-H2O was evaluated in Suzuki-Miyaura cross-coupling reactions of aryl bromides and chlorides with phenylboronic acid. Our novel complexes show excellent catalytic activities with high turnover numbers (TON) and high turnover frequencies (TOF) (e.g. for the Suzuki-Miyaura reaction: TON up to 370 and TOF up to 123.3 h(-1)). Both benzimidazolium salts 2a-e and complexes 3 have been characterized using spectroscopic data and elemental analysis. The antimicrobial activity of the N-heterocyclic carbene palladium complexes 3a-e varies with the nature of the ligands. Also, the IC50 values of both, complexes (3a-e) and benzimidazoles 2a-e, have been determined. In addition, the new palladium complexes were screened for their antitumor activity. Complexes 3e and 3d exhibited the highest antitumor effect with IC50 values 6.85 mu g/mL against MCF-7 and 10.75 mu g/mL against T47D, respectively. [GRAPHICS] .Öğe Ru(ii)-N-heterocyclic carbene complexes: synthesis, characterization, transfer hydrogenation reactions and biological determination(Royal Soc Chemistry, 2019) Boubakri, Lamia; Chakchouk-Mtibaa, A.; Al-Ayed, Abdullah S.; Mansour, L.; Abutaha, Nael; Harrath, Abdel Halim; Mellouli, L.A series of ruthenium(ii) complexes with N-heterocyclic carbene ligands were successfully synthesized by transmetalation reactions between silver(i) N-heterocyclic carbene complexes and [RuCl2(p-cymene)](2) in dichloromethane under Ar conditions. All new compounds were characterized by spectroscopic and analytical methods. These ruthenium(ii)-NHC complexes were found to be efficient precatalysts for the transfer hydrogenation of ketones by using 2-propanol as the hydrogen source in the presence of KOH as a co-catalyst. The antibacterial activity of ruthenium N-heterocyclic carbene complexes 3a-f was measured by disc diffusion method against Gram positive and Gram-negative bacteria. Compounds 3d exhibited potential antibacterial activity against five bacterial species among the six used as indicator cells. The product 3e inhibits the growth of all the six tested microorganisms. Moreover, the antioxidant activity determination of these complexes 3a-f, using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2 '-azinobis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS) as reagent, showed that compounds 3b and 3d possess DPPH and ABTS antiradical activities. From a concentration of 1 mg ml(-1), these two complexes presented a similar scavenging activity to that of the two used controls gallic acid (GA) and butylated hydroxytoluene (BHT). From a concentration of 10 mg ml(-1), the percentage inhibition of complexes 3b and 3d was respectively 70% and 90%. In addition, these two Ru-NHC complexes exhibited antifungal activity against Candida albicans. Investigation of the anti-acetylcholinesterase activity of the studied complexes showed that compounds 3a, 3b, 3d and 3e exhibited good activity at 100 mu g ml(-1) and product 3d is the most active. In a cytotoxicity study the complexes 3 were evaluated against two human cancer cell lines MDA-MB-231 and MCF-7. Both 3d and 3e complexes were found to be active against the tested cell lines showing comparable activity with examples in the literature.Öğe 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, SedatIn 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.Öğe Substituted NHC-PEPPSI-Pd(ii) complexes: synthesis, characterization, DFT calculations and catalytic application in thiazole C-H arylation(Royal Soc Chemistry, 2026) Evren, Enes; Boubakri, Lamia; Zouaghi, Mohamed Oussama; Gurbuz, Nevin; Ozdemir, Ismail; Arfaoui, Youssef; Attour, AnisIn this study, a series of functionalized benzimidazolium salts and their PEPPSI-type Pd(ii)NHC complexes 3a-g were synthesized and characterized by FT-IR, 1H NMR and 13C NMR spectroscopy, elemental analysis, and mass spectrometry. Quantum chemistry computations at the B3LYP/6-311G(d,p)/LANL2DZ level were used to examine the molecular structure, electronic characteristics, and chemical reactivity of the ligand and its Pd complex. The new salt and PEPPSI-type Pd-NHC complex were fully characterized by spectroscopic and analytical methods. Under the optimized reaction conditions, the catalytic activity of the NHC-PEPPSI-Pd(ii) complexes was tested by direct arylation of 2-n-propylthiazole and 4,5-dimethylthiazole with various aryl halides at 120 degrees C for 1 h and 3 h, respectively. It was observed that the palladium complexes gave high yields and were selective at the C5 and C2-positions of heteroaryl derivatives. Complex 3f, with an NHC substituted by a 3,4,5-trimethoxybenzyl group, showed the highest conversion probably due to the flexibility, electronic and mostly steric effects of this group.Öğe Synthesis of novel Ag(I)-N-heterocyclic carbene complexes soluble in both water and dichloromethane and their antimicrobial studies(Taylor & Francis Ltd, 2019) Boubakri, Lamia; Dridi, Khaireddine; Al-Ayed, Abdullah Sulaiman; Ozdemir, I.; Yasar, S.; Hamdi, NaceurThe interaction of the benzimidazolium salt with Ag2O in dichloromethane to prepare novel Ag(I)-N-heterocyclic carbene complexes has been carried out at room temperature for 48 h in the absence of light. The obtained complexes were identified and characterized by H-1 and C-13 NMR, FT-IR and elemental analysis techniques. In addition, it has been found that some of the complexes are antimicrobially active and show higher activity than the free ligand. Probably metal chelation affects significantly the antimicrobial behavior of the ligands. The minimum inhibitory concentration of the complexes was determined. The results indicated that these complexes exhibit antimicrobial activity.Öğe Synthesis, characterization and biological screening of N-heterocyclic carbene Ag(I) catalysts for aldehyde–amine–alkyne coupling reaction(Cellular and Molecular Biology Association, 2025) Boubakri, Lamia; Mnasri, Aziza; Salah, Donia Ben; Mansour, Lamjed; Gürbüz, Nevin; Özdemir, İsmail; Sauthier, MathieuN-heterocyclic carbenes (NHCs) are widely recognized for their applications in organometallic chemistry, catalysis, and pharmaceutical research due to their unique steric and electronic properties. In this study, we report the synthesis of six novel unsymmetrical N,N-disubstituted benzimidazolium salts (2a–f) and their corresponding silver-NHC complexes (3a–f). The structures of all compounds were characterized using nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FT-IR), and elemental analysis. The biological potential of these compounds was evaluated through in vitro antimicrobial assays against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, Candida albicans, and Candida glabrata. Additionally, anticancer activity was tested against A549, HCT116, and BEAS-2B cell lines, revealing promising results for some derivatives. Preliminary catalytic studies demonstrated the effectiveness of the silver-NHC complexes in A3-coupling reactions involving aldehydes, alkynes, and amines. These reactions yielded propargylamines with high conversion rates (up to 90%) using minimal catalyst amounts. This work highlights the dual utility of these compounds as both potent biological agents and efficient catalysts, paving the way for further exploration of their applications in medicinal chemistry and sustainable catalysis. © 2025 Cellular and Molecular Biology Association. All rights reserved.Öğe Tris(benzimidazole)(nitrato)silver(I) complexes: Synthesis, catalytic activities, and biological evaluation(Elsevier, 2026) Boubakri, Lamia; Hallab, Wissem; Karci, Huseyin; Attour, Anis; Dundar, Muhammed; Ozdemir, Lknur Lknur; Gurbuz, NevinIn this study new N-alkylbenzimidazole derivatives 1a-e and their related tris(benzimidazole)(nitrato)silver(I) complexes 2a-e were prepared and characterized by FT-IR, 1H,13C{1H} NMR spectroscopy, and elemental analysis, which support the proposed structures. Further confirmations of structural details were provided by a single-crystal X-ray. A single crystal of tris(N-alkylbenzimidazole)(nitrato)silver(I) 2e shows that the coordination geometry around Ag slightly distorted tetrahedral geometry. Further, the synthesized compounds were evaluated for their antimicrobial activities against bacteria Escherichia coli, P. aeruginosa, S. aureus, and the fungal strains C. albicans and C. glabrata. The results indicated that the activity shown by the tested compounds, especially against Gram-negative bacteria, is valuable for the development of new treatment options against these microorganisms. Especially, the drug development potential of N-alkyl-5,6-dimethylbenzimdazole 1b and complexes 2b, 2c, and 2e showing the highest antimicrobial activity. Also, the alkylbenzimidazole substituent 1b and 1e and the Tris(1-alkylbenzimidazole)silver(I) 2c showed remarkable activity against fungi strains. Complexes 2a, 2b, 2c, 2d, and 2e also showed high cytotoxicity. The synthesized complexes demonstrated higher cytotoxicity relative to Cisplatin across all tested cell lines. Furthemore, a mild catalytic protocol for benzaldehyde, amine, and phenylacetylene coupling (A3-coupling) allows for the selective synthesis of propargyl amines using N-alkylbenzimidazole silver(I) nitrate catalysts with conversion of 100 %. The present approach is environmentally benign and water is generated as the sole by product.
