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Öğe Alkylation of morpholine and prolidine by phthalimide substituted Ru(II)- NHC catalysts(Pergamon-Elsevier Science Ltd, 2024) Akkoc, Mitat; Gurbuz, Nevin; Ozdemir, IsmailIn this study, a series of benzimidazolium salts and silver-benimidazol-2-ylidene complexes were synthesized. The obtained silver complexes were converted into Ru(II)- benimidazol-2-ylidene complex using the transmetallation method. After elucidating the structures of these Ru(II)-NHC compounds, the synthesized ruthenium complexes were used in the alkylation reaction of cyclic amines to synthesize valuable derivatives such as pyrrolidine and morpholine. Pyrrolidine derivatives are extensively studied for their antimicrobial, antiviral, antifungal, anticancer, anti-inflammatory, anticonvulsant, cholinesterase inhibition, and carbonic anhydrase inhibition properties. Morpholine derivatives are particularly studied in the context of central nervous system (CNS) diseases. The yield of the catalytic products obtained was determined by GC. High selectivity and yield were achieved in the alkylation reactions of heterocyclic structures.Öğe Cationic versus anionic Pt complex: The performance analysis of a hybrid-capacitor, DFT calculation and electrochemical properties(Pergamon-Elsevier Science Ltd, 2019) Akkoc, Mitat; Demirel, Serkan; Oz, Erdinc; Altin, Serdar; Bayri, Ali; Dorcet, Vincent; Roisnel, ThierryThe synthesis and characterization of cationic versus anionic platinum(II) complex of the type [PtCl3(DMSO)](-)[NHC](+) (NHC: N-heterocyclic carbene) is reported for the first time. The complex 3 was synthesized from silver(I)-NHC2, and K-2[PtCl4] in DMSO at 80 degrees C under exclusion of light. The ionic platinum(II) complex was obtained in high yield and fully characterized by H-1, C-13, Pt-195 NMR and HRMS spectroscopy, X-ray diffraction and elemental analysis. The structural properties of the complex were investigated by using Gaussian suit and the obtained parameters were crosschecked with the X-ray data. The HOMO-LUMO energies and electrostatic surface mapping of the complex were calculated and the results were discussed with the capacitive properties of the complex. Electrochemical analysis by cyclic voltammetry (CV) of the complex shows reversible redox peaks about platinum center. The complex was used as an electrode material for the capacitor device and result is promising that the highest performance of complex 3 was found as 10.22 F/g. (C) 2018 Elsevier Ltd. All rights reserved.Öğe An Efficient Protocol for Palladium N-Heterocyclic Carbene-Catalysed Suzuki-Miyaura Reaction at room temperature(Wiley-V C H Verlag Gmbh, 2017) Akkoc, Mitat; Imik, Fatma; Yasar, Sedat; Dorcet, Vincent; Roisnel, Thiery; Bruneau, Christian; Ozdemir, IsmailThe palladium-N-heterocyclic carbene complexes have been synthesised from 1,3-bis-(N-alkyl) benzimidazolium salts and catalytic activity of complexes have been tested on Suzuki-Miyaura coupling reaction for aryl bromides with substituted arylboronic acids at room temperature in i-PrOH/water. Structural characterisation of palladium complex 2b was determined by x-ray crystallography. A convenient and effective protocol has been evolved that has several superior advantages, including very low catalyst loading, vide range of substrate tolerance, excellent yields, room temperature, totally green solvents, short reaction times, up to 59750 h(-1) TOF (Turn Over Frequency) value with aryl bromide substrates and very simple procedure.Öğe Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki-Miyaura Cross-Coupling Reaction(Springer, 2022) Akkoc, Mitat; Bugday, Nesrin; Altin, Serdar; ozdemir, Ismail; Yasar, SedatA novel Pd-NHC functionalized magnetic Fe3O4@SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki-Miyaura C-C bond formation reactions. The Fe3O4@SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), Energy Dispersive X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES) analysis was used to determine the exact amount of Pd (0.33 wt%) in Fe3O4@SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst's structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki-Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a K2CO3 at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products in excellent yields with spectacular TOFs values (up to 1,960,339 h(-1)); in the presence of 1 mg of Fe3O4@SBA-15@NHC-Pd catalyst (contains 3.1 x 10(-6) mol% Pd) at room temperature in aqueous media. After reusability experiments, it is found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. Graphic AbstractÖğe Investigation of potential hybrid capacitor property of chelated N-Heterocyclic carbene Ruthenium(II) complex(Elsevier Science Sa, 2018) Akkoc, Mitat; Oz, Erdinc; Demirel, Serkan; Dorcet, Vincent; Roisnel, Thierry; Bayri, Ali; Bruneau, ChristianThe synthesis of chelated ruthenium(II) complex type Ru(eta(6)-HMB) (NHC) Cl (NHC = N-heterocyclic carbene, HMB = hexamethylbenzene) is presented. The ruthenium(II)-NHC complex 6 was obtained in good yield and was fully characterised by NMR spectroscopy, X-ray diffraction and HRMS analysis. Electrochemical analysis by cyclic voltammetry (CV) revealed reversible redox behaviour at the ruthenium centre in 6. DFT studies and the catalytic activity of complex 6 on transfer hydrogenation reaction of aryl ketones are also presented. The potential hybrid capacitor applications of Ru-NHC complex is discussed and reported firstly in the literature. It was found that the highest performance was found at 20.1 F/g, which is a promising result for energy storage applications. (c) 2018 Elsevier B.V. All rights reserved.Öğe Magnetite@MCM-41 nanoparticles as support material for Pd-N-heterocyclic carbene complex: A magnetically separable catalyst for Suzuki-Miyaura reaction(Wiley, 2021) Akkoc, Mitat; Bugday, Nesrin; Altin, Serdar; Yasar, SedatThe Magnetite@MCM-41@NHC@Pd catalyst was obtained with Pd metal bound to the NHC ligand anchored to the surface of Fe3O4@MCM-41. It was characterized by Fourier transform infrared (FTIR) spectroscopy, transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy disperse X-ray analysis (EDX), thermogravimetric analysis (TGA), differential thermal analysis (DTA), and scanning electron microscopy (SEM). The amount of Pd in the Magnetite@MCM-41@NHC@Pd was measure by inductively coupled plasma-optical emission spectroscopy (ICP-OES) analysis. The catalytic activity of Magnetite@MCM-41@NHC@Pd heterogeneous catalyst done on Suzuki-Miyaura reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions afforded excellent yields and up to 408404 Turnover Frequency (TOF) h(-1) in the presence of 2 mg of Magnetite@MCM-41@NHC@Pd catalyst (0.0564 mmol g(-1), 0.01127 mmol% Pd) at room temperature in 2-propanol/H2O (1:2). Moreover, Magnetite@MCM-41@NHC@Pd catalyst was recover by applying the magnet and reused for another reaction. The catalyst showed excellent structural and chemical stability and reused ten times without a substantial loss in its catalytic performance.Öğe Molecular docking and in vitro anticancer studies of silver(I)-N-heterocyclic carbene complexes(Elsevier Sci Ltd, 2022) Akkoc, Mitat; Khan, Siraj; Yuce, Hande; Turkmen, Nese Basak; Yasar, Seyma; Yasar, Sedat; Ozdemir, IsmailA series of symmetric and unsymmetrical benzimidazolium-based N-heterocyclic carbene (NHC) precursors (1a-i) and their silver complexes (2a-i) have been synthesized. The Ag(I)-NHC complexes were characterized by H-1, C-13 {H-1} NMR, FTIR, LC/MS-QTOF, and elemental analysis. Anticancer and cytotoxic activity of all Ag(I)-NHC complexes were tested against healthy fibroblast cell line (L929), breast cancer cell line (MCF-7), and neuro-blastoma cell line (SH-SY5Y) by MTS [3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4sulfo-phenyl)-2H-tetrazolium] assay. The 2b, 2c, 2e, 2g, 2h, and 2i complexes showed higher cytotoxicity than cisplatin against SH-SY5Y and MCF-7 and lower cytotoxic activity against L929 cell lines. Because of their high cytotoxic activity against cancer cells and low cytotoxicity against healthy fibroblast cell lines, the 2b, 2c, 2e, 2g, 2h, and 2i are expected to be new lead compounds. In addition, molecular docking studies were performed to explore the binding interactions of silver complexes with the enzyme to explore new anticancer compounds. Furthermore, ADME properties of all complexes were predicted to explore lead-like characteristics and may be a potential drug candidate for cancer treatment.Öğe N-heterocyclic carbene Pd(II) complex supported on Fe3O4@SiO2: Highly active, reusable and magnetically separable catalyst for Suzuki-Miyaura cross-coupling reactions in aqueous media(Elsevier Science Sa, 2021) Akkoc, Mitat; Bugday, Nesrin; Altin, Serdar; Kiraz, Nadir; Yasar, Sedat; Ozdemir, IsmailA new type magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was fabricated and characterized by Fourier Transform Infrared (FTIR) spectroscopy, Transmission Electron Microscopy (TEM), X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Energy Disperse X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA), and Scanning Electron Microscopy (SEM). The loading amount of Palladium (Pd) to magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs was measured by Inductively Coupled Plasma-Optical Emission Spectroscopy (ICP-OES) analysis. The catalytic activity of magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was examined on Suzuki-Miyaura cross-coupling reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions yielded excellent results and high TOF (up to 76528 h(-1)) in the presence of 2 mg of Fe3O4@SiO2@NHC@Pd-MNPs catalyst (0.0197 mmolg(-1), 0.00394 mmol%Pd) at 80 degrees C in 2-propanol/H2O (1:2). In addition, the magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs catalyst was easily recovered by using an external Nd-magnet and reused for the Suzuki cross-coupling reactions. The catalyst showed strong structural and chemical stability and was reused six times without losing its catalytic activity substantially. (C) 2021 Elsevier B.V. All rights reserved.Öğe A novel ditopic ring-expanded N-heterocyclic carbene ligand-assisted Suzuki-Miyaura coupling reaction in aqueous media(Pergamon-Elsevier Science Ltd, 2017) Karaca, Emine Ozge; Akkoc, Mitat; Tahir, Muhammad Nawaz; Arici, Cengiz; Imik, Fatma; Gurbuz, Nevin; Yasar, SedatA series of seven-membered ditopic ring-expanded N-heterocyclic carbene (dre-NHC) precursors, bearing sterically demanding and electron-rich aryl groups, were synthesised in moderate yields via the reaction of 1,2,4,5-tetrakis(bromomethyl)benzene with the corresponding N,N'-diarylformamidines in the presence of K2CO3 in acetonitrile under an air atmosphere. All new compounds were characterised by HRMS, NMR spectroscopy, and microanalysis, as well as X-ray crystallography for compound lc. The development of an efficient catalytic system for the Suzuki-Miyaura coupling reaction of aryl chlorides with various boronic acids was also investigated using the in situ generated dre-NHC ligands. (C) 2017 Elsevier Ltd. All rights reserved.Öğe Palladium N-heterocyclic carbene catalysts for synthesis of diaryl ethers(Georg Thieme Verlag Kg, 2008) Akkoc, Mitat; Gurbuz, Nevin; Cetinkaya, Engin; Ozdemir, IsmailNovel functionalized 1,3-dialkylimidazolinium (LH) salts as precursors for N-heterocyclic carbenes (NHCs) have been prepared and successfully applied in the palladium-catalyzed synthesis of diaryl ethers and arylation of benzaldehydes. An efficient catalyst system was prepared in situ from Pd(OAc)(2), 1,3-dialkylimidazolinium bromides (LHBr), and NaH.Öğe Pd-N-Heterocyclic carbene catalysed Suzuki-Miyaura coupling reactions in aqueous medium(Arkat Usa Inc, 2018) Karaca, Emine Ozge; Akkoc, Mitat; Yasar, Sedat; Ozdemir, IsmailA new series of methyl substituted imidazole-based N-heterocyclic carbene (NHC) palladium complexes (PdCl2(L-1)NHC(L-1 =pyridine) is reported. Structural definitions of Pd-PEPPSI complexes were determined by NMR spectroscopy, elemental analysis and LC-MS spectroscopy techniques. To evolve a more efficient catalytic system for electronically different aryl chloride substrates on the Suzuki cross-coupling reaction, complexes were used as pre-catalyst. Activity of palladium(II)-NHC complexes screened under mild reaction conditions in aqueous media. With this catalytic system, the reaction proceeded in moderate or good yields with low catalyst loading (0.1 mol%). [GRAPHICS] .Öğe Protonated water-soluble N-heterocyclic carbene ruthenium(II) complexes: Synthesis, cytotoxic and DNA binding properties and molecular docking study(Elsevier Science Sa, 2018) Akkoc, Mitat; Balcioglu, Sevgi; Gurses, Canbolat; Tok, Tugba Taskin; Ates, Burhan; Yasar, SedatNew benzimidazolium salts 1a-d having methylpyridine group on the side chain, have been synthesized and reacted with Ag2O to produce Ag(I)-N-heterocyclic carbene (NHC) complexes 2a-d. Ag(I)-N-heterocyclic carbene (NHC) complexes were used as a carben transfer agents to synthesize water-soluble ruthenium(II)-NHC complexes 4a-d. All synthesized compounds were fully characterized by H-1 and C-13 NMR and HRMS spectroscopic techniques. Anticancer potential and IC50 values of ruthenium(II)-NHC complexes were evaluated by MTT assay against human colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines. The IC50 value of water-soluble ruthenium(II)-NHC complex 4d demonstrated remarkable cytotoxic activity against Caco-2 (18.0 +/- 1) and MCF-7 (23.8 +/- 0.5) cell lines. Also, 4d has better DNA binding capacity than 4a-c. DS 2017 R2 was used to exert molecular docking for understanding interactions between the water-soluble ruthenium(II)-NHC complexes and DNA. These complexes have been highlighted as a new type of drug. (C) 2018 Elsevier B.V. All rights reserved.Öğe Synthesis and biological evaluation of Au-NHC complexes(Wiley, 2022) Ekinci, Orhan; Akkoc, Mitat; Khan, Siraj; Yasar, Sedat; Gurses, Canbolat; Noma, Samir; Balcioglu, SevgiNew seven Au-N-heterocyclic carbene (NHC) complexes have been synthesized via transmetalation from Ag-NHC complexes. NHC salts, Ag-NHC, and Au-NHC complexes were fully characterized by widely used spectroscopic techniques. The molecular and crystal structures of 3b and 3f Au-NHC complexes were clarified through the single-crystal X-ray diffraction method. According to X-ray diffraction analysis results, the coordination geometry around Au(I) atoms in the complexes are revealed to be almost linear with C-Au-Cl angle. Anticancer activity, DNA binding, xanthine oxidase (XO) inhibitory activity studies, and molecular docking studies were evaluated for all Au-NHC complexes to explore the binding mechanism at the active site. The IC50 value of Au-NHC complexes against human colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines was defined by MTT assay. The IC50 values for MCF-7 in the range of 5.2 +/- 2 to 152.4 +/- 1 mu M and Caco-2 5.2 +/- 1 to 152.7 +/- 2 mu M showed that 3a, 3b, 3c, 3d, and 3g have better anticancer activity than Cisplatin incredibly complex 3a against both cancer cell line. All Au-NHC complexes showed excellent antimicrobial activity against different bacteria and fungi. 3a was the complex that exhibited the best antimicrobial activity here as well. The XO inhibitory activity experimental results indicated that all gold complexes showed remarkable inhibition activity against XO compared to the generally used standard, allopurinol. The range of IC50 value was determined from 0.407 to 2.681 mu M. 3d complex showed the lowest IC50 value at 0.407 mu M. DNA binding experiments were performed using agarose gel electrophoresis to observe the ability of synthesized Au-NHC complexes to interact with the supercoiled pUC19 plasmid DNA. Molecular docking studies were performed to determine the binding mode of all active compounds against the XO enzyme, antibacterial, antifungal, and MCF-7 cell lines.Öğe Synthesis and catalytic activity of ionic palladium N-heterocyclic carbene complexes(Tubitak Scientific & Technological Research Council Turkey, 2019) Yasar, Sedat; Akkoc, Mitat; Ozdemir, Namik; Ozdemir, IsmailThe synthesis of 3 benzimidazole-based ionic Pd(II)-NHC complexes (NHC: N-heterocyclic carbene) is presented. The structures of the complexes are as follows: [NHC-PdBr3](-) [NHC](+). The ionic palladium(II)-NHC complexes were synthesized in high yields and were fully characterized by nuclear magnetic resonance spectroscopy, X-ray diffraction, LC-MS/MS, and elemental analysis. These complexes have been identified as active catalysts in Suzuki-Miyaura reactions in a solution of 2-propanol and water at room temperature for different aryl bromides.Öğe Synthesis and investigation of antiproliferative activity of Ru-NHC complexes against C6 and HeLa cancer cells(Tubitak Scientific & Technological Research Council Turkey, 2022) Pasahan, Ramazan; Akkoc, Mitat; Yasar, Seyma; Kul Koprulu, Tugba; Tekin, Saban; Yasar, Sedat; Ozdemir, IsmailThe 2-methylpyridine, 2-diethylaminoethyl, and isopentyl linked a series of symmetric and unsymmetric benzimidazolium salts 2a-e were prepared and used in the synthesis of silver-N-heterocyclic carbene (NHC) complexes (3a-e). The Ru(II)-NHC complexes (4a-h) were synthesized via transmetalation reaction from 3a-e. 4a-h complexes were converted to Ru(II)-NHC. HCl complexes (5a-h) by HCl solution of diethyl ether and characterized by different spectroscopic techniques such as H-1 and C-13 NMR, LC/MS-Q-TOF, FT-IR, elemental analysis, and melting point detection. We examined the effect of the structural difference of complexes on anticancer activity via different arenes and metal centers. Antiproliferative activity of 5a-h and 3a was tested against human cervix adenocarcinoma (HeLa) and rat glioblastoma (C6) cell lines by ELISA assay. The IC50 value of 5b, 5c and 5e complexes exhibited good cytotoxic activity than cisplatin on C6 (14.2 +/- 0.5 mM; 16.2 +/- 0.4 mM; 24.2 +/- 0.7 mM, respectively) and HeLa (11.1 +/- 0.5 mM; 13.7 +/- 0.3 mM; 22.8 +/- 0.8 mM, respectively) cell lines.
