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    Anticancer, antimicrobial and antiparasitical activities of copper(I) complexes based on N-heterocyclic carbene (NHC) ligands bearing aryl substituents
    (Taylor & Francis Ltd, 2020) Touj, Nedra; Al Nasr, Ibrahim S.; Koko, Waleed S.; Khan, Tariq A.; Ozdemir, Ismail; Yasar, Sedat; Mansour, Lamjed
    New benzimidazolium salts were synthesized as N-heterocyclic carbene precursors. These NHC precursors were metallated with Cu2O and CuI in acetone and water under reflux to give novel copper(I) complexes. The structures of these benzimidazolium salts and copper(I) complexes were characterized on the basis of elemental analysis, H-1 NMR, C-13 NMR, IR and LC-MS spectroscopic techniques. The (NHC)Cu(I) complexes 3-4 were tested against MCF7 and MDA-MB-231 cancer cells, Escherichia coli, methicillin-resistant Staphylococcus aureus (MRSA) and Candida albicans microorganisms, Leishmania major promastigotes and amastigotes, Toxoplasma gondii parasites and against Vero cell line in vitro. The synthesized copper NHC carbene complex 4b (1,3-bis(2,3,4,5,6-pentamdthylbenzyl)-2,3-dihydro-1H-benzo[d]imidazol-2-yl)copper(I) chloride) was the most active against MCF7 cancer cells (half growth Inhibition Concentrations (IC50) = 0.3 mu g mL(-1)), as well as the most potent antimicrobial against E. coli (inhibition zone (IZ) = 23.3 mm), MRSA (IZ = 25.5 mm) and C. albicans (IZ = 28.5 mm) besides its antileishmanial activities against L. major promastigotes and amastigotes (IC50 < 0.04 mu g mL(-1)). Compound 4c (1,3-bis(4-(tert-butyl)benzyl)-2,3-dihydro-1H-benzo[d]imida-zol-2-yl)copper(II) bromide) is the most potent anticancer against MDA-MB-231 cancer cells IC50 = 0.4 mu g mL(-1)). Compound 4e (5,6-dimethyl-1,3-bis(2,4,6-trimethylbenzyl)-2,3-dihydro-1H-benzo[d]imidazol-2-yl)copper(I) chloride) is the best suitable antitoxoplasmal drug candidate due to its SI of 16.5. These candidates need further study to identify mode of action and drug standardization.
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    Biological Activities of NHC-Pd(II) Complexes Based on Benzimidazolylidene N-heterocyclic Carbene (NHC) Ligands Bearing Aryl Substituents
    (Mdpi, 2020) Al Nasr, Ibrahim; Touj, Nedra; Koko, Waleed; Khan, Tariq; Ozdemir, Ismail; Yasar, Sedat; Hamdi, Naceur
    N-heterocyclic carbene (NHC) precursors (2a-i), their pyridine-enhanced precatalyst preparation stabilization and initiation (PEPPSI)-themed palladium N-heterocyclic carbene complexes (3a-i) and palladium N-heterocyclic triphenylphosphines complexes (4a-i) were synthesized and characterized by elemental analysis and H-1 NMR, C-13 NMR, IR, and LC-MS spectroscopic techniques. The (NHC)Pd(II) complexes 3-4 were tested against MCF7 and MDA-MB-231 cancer cells, Escherichia coli, methicillin-resistant Staphylococcus aureus (MRSA), Candida albicans microorganisms, Leishmania major promastigotes and amastigotes, Toxoplasma gondii parasites, and Vero cells in vitro. The biological assays indicated that all compounds are highly active against cancer cells, with an IC50 < 1.5 mu g mL(-1). Eight compounds proved antibacterial and antileishmanial activities, while only three compounds had strong antifungal activities against C. albicans. In our conclusion, compounds 3 (b, f, g, and h) and 4b are the most suitable drug candidates for anticancer, antimicrobial, and antiparasitical.
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    An efficient (NHC) Copper (I)-catalyst for azide-alkyne cycloaddition reactions for the synthesis of 1,2,3-trisubstituted triazoles: Click chemistry
    (Elsevier Science Sa, 2017) Touj, Nedra; Ozdemir, Ismail; Yasar, Sedat; Hamdi, Naceur
    In this study a series of new benzimidazolium salts (2a-c) were synthesized from the reaction of 5,6-dimethyl-1-(alkylbenzyl)-1H-benzo[d] imidazole with various alkyl halides. These salts were used to synthesize cupper N-heterocyclic carbene (Cu-NHC) complexes 3-4. The obtained (NHC) Copper (I) complexes 3-4 were characterized by FT-IR, NMR (H-1 and C-13) spectroscopic methods, mass spectrometry (EI-MS and HRMS) and elemental analysis. These novel cupper complexes 3-4 were used as a catalyst for alkyne - azide cycloaddition (CuAAC) reaction. Several triazoles 7 have been synthesized. This catalytic system fulfils the requirements of click chemistry with its mild and convenient conditions, notably in water at room temperature with low catalyst loading and simple isolation with no purification step. (C) 2017 Elsevier B.V. All rights reserved.
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    Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities
    (Royal Soc Chemistry, 2018) Touj, Nedra; Al-Ayed, Abdullah S.; Sauthier, Mathieu; Mansour, Lamjed; Harrath, Abdel Halim; Al-Tamimi, Jamil; Ozdemir, Ismail
    N,N-Substituted benzimidazole salts were successfully synthesized and characterized by H-1-NMR, C-13 {H-1} NMR and IR techniques, which support the proposed structures. Catalysts generated in situ were efficiently used for the carbonylative cross-coupling reaction of 2 bromopyridine with various boronic acids. The reaction was carried out in THF at 110 degrees C in the presence of K2CO3 under inert conditions and yields unsymmetrical arylpyridine ketones. All N,N-substituted benzimidazole salts 2a-i and 4a-i studied in this work were screened for their cytotoxic activities against human cancer cell lines such us MDA-MB-231, MCF-7 and T47D. The N,N-substituted benzimidazoles 2e and 2f exhibited the most cytotoxic effect with promising cytotoxic activity with IC50 values of 4.45 g mL(-1) against MDA-MB-231 and 4.85 g mL(-1) against MCF7 respectively.
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    Experimental and quantum mechanical investigation on two N-heterocyclic carbene palladium complexes
    (Taylor & Francis Ltd, 2021) Ozdemir, Namik; Touj, Nedra; Yasar, Sedat; Hamdi, Naceur; Ozdemir, Ismail
    Two palladium complexes bearing different ligands such as N-heterocyclic carbene (NHC), pyridine and phosphines were synthesized and characterized by FT-IR spectroscopy, X-ray crystallography and quantum-chemical computations. DFT calculations have been performed at HSEh1PBE/SDD level of theory. Intermolecular interactions have been studied through two-dimensional fingerprint plots based on Hirshfeld surface analysis. Structural parameters and spectroscopic properties of the complexes are well interpreted by DFT and TD-DFT calculations.
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    Palladium PEPPSI complexes: Synthesis and catalytic activity on the Suzuki-Miyaura coupling reactions for aryl bromides at room temperature in aqueous media
    (Elsevier Science Sa, 2018) Touj, Nedra; Gurbuz, Nevin; Hamdi, Naceur; Yasar, Sedat; Ozdemir, Ismail
    A new series of palladium N-heterocyclic carbene complexes having methoxyethyl on the side chain (3a-d, 4a-e) have been synthesized and fully characterized by NMR, HRMS and IR. Next, the palladium-NHC-PEPPSI complexes 3a-e and 4a-e were used as catalyst in Suzuki-Miyaura coupling reactions were investigated for aryl bromides at room temperature in aqueous media. 3a-d and 4a-e complexes showed good catalytic activity for electron-donating or electron-drawing aryl bromides with arylboronic acid. Complex 4b exhibited higher activity compared to other analogues due to bearing more electronically donating NHC ligands. (C) 2018 Elsevier B.V. All rights reserved.
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    Pd-PEPPSI-type expanded ring N-heterocyclic carbene complexes: synthesis, characterization, and catalytic activity in Suzuki-Miyaura cross coupling
    (Taylor & Francis Ltd, 2024) Alnasser, Sarah; Touj, Nedra; Alomar, Suliman; Mansour, Lamjed; Sauthier, Mathieu; Gurbuz, Nevin; Ozdemir, Ismail
    In this work, we synthesized a series of six unsymmetrical benzimidazolium salts 2 and their pyridine-enhanced precatalyst preparation stabilization and initiation (PEPPSI)-themed palladium N-heterocyclic carbene complexes [PdCl2(NHC)(Py)]. All the products were isolated in satisfactory yields (75-85%). The synthesis of these novel palladium PEPPSI complexes involved in reacting NHC precursors with PdCl2 in pyridine at 60 degrees C in the presence of excess K2CO3. The structures of all compounds have been characterized by H-1 NMR, C-13 NMR, HRMS and IR spectroscopy, as well as elemental analysis techniques, which support the proposed structures. The catalytic activity of the six complexes was assessed in the Suzuki-Miyaura cross-coupling of phenylboronic acid and aryl halides. The reactions required only a low catalyst loading (0.1 mol%) and were carried out under mild aerobic conditions in a green, water-based solvent mixture.
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    Sonogashira cross-coupling reaction catalysed by mixed NHC-Pd-PPh3 complexes under copper free conditions
    (Elsevier Science Sa, 2018) Touj, Nedra; Yasar, Sedat; Ozdemir, Namik; Hamdi, Naceur; Ozdemir, Ismail
    Mixed NHC-Pd-PPh3 complexes with a methoxyethyl-substituted N-heterocyclic carbene ( NHC) were synthesised and characterised by NMR, HRMS, elemental analysis and X-ray crystallography for complex 3b. These complexes were applied to Sonogashira cross-coupling reactions between aryl bromides and phenylacetylene in DMF at 80 degrees C. All palladium complexes were stable and showed high catalytic activity in Sonogashira reactions at low catalyst loading and ambient reaction conditions. (c) 2018 Elsevier B.V. All rights reserved.
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    Synthesis of palladium complexes containing benzimidazole core and their catalytic activities in direct C-H functionalization of five-membered heterocyclic bioactive motifs
    (Elsevier, 2024) Touj, Nedra; Bensalah, Donia; Mansour, Lamjed; Sauthier, Mathieu; Gurbuz, Nevin; Ozdemir, Ismail; Hamdi, Naceur
    Herein, we reported the synthesis of nine new PEPPSI-Pd(II)-N-heterocyclic carbene (NHC) complexes 3a-h containing benzimidazole core and examined their catalytic activities in the direct arylation of heteroaromatic species with aryl bromides and arylchlorides. Nine new Pd benzimidazole complexes were synthesized and their structures were elucidated by 1H and 13C NMR spectroscopy, FT-IR spectroscopy, and elemental analysis methods. In the 13C NMR spectra, NCHN peaks of Pd(II) complexes were observed between 159.7-161.5 ppm. Further, direct arylation reaction, using KOAc as base and DMAc as solvent under inert conditions, were carried out with the synthesized complexes in the presence of various aryl bromides and chlorides, and 2-acetyl furan, and furfuryl acetate 2-acetylthiophene and N-methylpyrrole-2- carboxaldehyde. Moreover, moderate to hig yields were obtained in the direct arylation of heteroarenes and aryl bromides under 1 mol% catalyst loading at 150 degrees C for 2 h loading conditions. The results showed that electron-donating and electron-withdrawing substituents on the aryl halides might produce coupling products in good yields in the presence of complexes 2a-d. Taken together, our findings are expected to contribute to the synthesis and design of palladium complexes containing benzimidazole core structures.