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1,3-Bis[(5-aminofuran-2-yl) methyl]3,4,5,6-tetrahydropyrimidin-1-ium hexafluorophosphate
(Int Union Crystallography, 2013) Akkurt, Mehmet; Akkoc, Senem; Gok, Yetkin; Tahir, Muhammad Nawaz
The asymmetric unit of the title salt, C16H21N2O2 (+) center dot PF6 (-), contains half of the whole ion pair, which has crystallographic mirror symmetry. Two F atoms related by the mirror plane are disordered over two sites of equal occupancy. The dihedral angle between the central ring and the furan ring is 59.3 () degrees. In the crystal, the anions and cations are linked through CH center dot center dot center dot F interactions, forming a three- dimensional network.
A benzimidazolium salt induces apoptosis and arrests cells at sub-G1 phase in epithelial ovarian cancer cells (vol 51, 66, 2024)
(Springer, 2024) Akar, Sakine; Cakir, Mustafa; Ozkol, Halil; Akkoc, Senem; Ozdem, Berna
[Abstract Not Available]
Benzimidazolium-based novel silver N-heterocyclic carbene complexes: synthesis, characterisation and in vitro antimicrobial activity
(Taylor & Francis Ltd, 2016) Sari, Yakup; Akkoc, Senem; Gok, Yetkin; Sifniotis, Vicki; Ozdemir, Ilknur; Gunal, Selami; Kayser, Veysel
This study reports the synthesis, characterisation and antimicrobial activity of five novel silver N-heterocyclic carbene (Ag-NHC) complexes obtained by N-propylphthalimide and N-methyldioxane substituted benzimidazolium salts with silver oxide. The reactions were performed at room temperature for 24 h in the absence of light. The obtained complexes were identified and characterised by H-1 and C-13 NMR, FT-IR and elemental analysis techniques. The minimum inhibitory concentration (MIC) of the complexes was determined for E. coli, P. aeruginosa, E. faecalis, S. aureus, C. tropicalis and C. albicans in vitro through agar and broth dilution. The results indicated that these complexes exhibit antimicrobial activity. In particular, complex 3 presented the significant broad spectrum antimicrobial activity.
BIOLOGICAL ACTIVITY EVALUATION OF NOVEL N-HETEROCYCLIC CARBENE PRECURSORS
(Int Journal Pharmaceutical Sciences & Research, 2017) Akkoc, Senem; Gok, Yetkin; Erdogan, Hulya; Albayrak, Sevil
Five novel benzimidazolium salts were synthesized as N-heterocyclic carbene (NHC) precursors (1a-e). They were characterized by different techniques. The antimicrobial activities of these compounds were tested. The compounds showed moderate activity against three Gram (+) and seven Gram (-) bacteria in comparison to tetracycline, which was used as the standard antibiotic, whereas all the compounds (1a-e) showed no activity against the test yeast C. albicans.
Carbon-carbon bond formation catalyzed by PEPPSI Pd-NHC
(Elsevier Science Sa, 2017) Akkoc, Senem; Ilhan, Ilhan Ozer; Gok, Yetkin; Kayser, Veysel
Five new palladium complexes were efficiently synthesized from the reaction of benzimidazolium salts, potassium carbonate (K2CO3) and palladium chloride (PdCl2) in pyridine (for 3-5) or 3-chloropyridine (for 6 and 7). The synthesized complexes were characterized and tested in Suzuki-Miyaura cross-coupling reaction as catalysts. In the presence of catalysts 3-7, biaryl products were obtained in moderate yields when phenylboronic acid was used as boronic acid derivative. However, the coupling of thianaphthene-2-boronic acid with 1-chloro-4-nitrobenzene generated low yields although a longer period of time was used in comparison to the coupling of phenylboronic acid with aryl chlorides. (C) 2017 Elsevier B.V. All rights reserved.
Catalytic activities in direct arylation of novel palladium N-heterocyclic carbene complexes
(Wiley, 2014) Akkoc, Senem; Gok, Yetkin
Eight novel palladium N-heterocyclic carbene (Pd-NHC) complexes were synthesized by the reaction of chloro 1,3-dialkylbenzimidazolin-2-ylidene silver(I) complexes with bis(benzonitrile)palladium(II) chloride in dichloromethane. These eight Pd-NHC complexes are as follows: bis[1-phenyl-3-(2,4,6-trimethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-phenyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-phenyl-3-(2,3,4,5,6-pentamethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-phenyl-3-(3,4,5-trimethoxybenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-(2-diethylaminoethyl)-3-(3-methylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II), bis[1-(2-diethylaminoethyl)-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II),bis[1-(2-morpholinoethyl)-3-naphthalenomethylbenzimidazol-2-ylidene]dichloropalladium(II) and bis[1-(2-morpholinoethyl)-3-(2-methylbenzyl)benzimidazol-2-ylidene]dichloropalladium(II). Also, these synthesized complexes were fully characterized using Fourier transform infrared, H-1 NMR and C-13 NMR spectroscopic methods and elemental analysis techniques. These synthesized novel Pd-NHC complexes were tested as catalysts in the direct arylation of 2-n-butylthiophene, 2-n-butylfuran and 2-isopropylthiazole with various aryl bromides at 130 degrees C for 1 h. The complexes showed very good catalytic activities in these reactions. Copyright (c) 2014 John Wiley & Sons, Ltd.
Catalytic activities in the direct C5 arylation of novel palladium N-heterocyclic carbene complexes containing benzimidazol-2-ylidene nucleus
(Elsevier Science Sa, 2014) Akkoc, Senem; Gok, Yetkin; Akkurt, Mehmet; Tahir, Muhammad Nawaz
New palladium N-heterocyclic carbene (NHC) complexes (1a-e) were synthesized in very good yields by the reaction of 1-phenyl-3-alkylbenzimidazolium salts with Pd(OAc)(2) in dimethyl sulfoxide. These synthesized complexes were fully characterized using elemental analyses, FT-IR, H-1 NMR, C-13 NMR and LC-MS (for 1a, 1c and 1e) spectroscopy data. Also, the molecular structure of the bis[1-phenyl-3-(2methyl-1,4-benzodioxane)benzimidazol-2-ylidene] dibromopalladium(II) complex (1d) was structurally characterized by single crystal X-ray diffraction study. The new Pd-II complexes (1a-e) were tested as catalysts in the direct C5 arylation of 2-n-butylfuran, 2-n-butylthiophene and 2-n-propylthiazole with various aryl bromides at 130 degrees C for 1 h. Also, some experiments were carried out by using aryl chlorides in order to be used for comparison. The results are reported herein. These complexes exhibited quite high catalytic activities under the given conditions. (C) 2014 Elsevier B.V. All rights reserved.
Chlorido[1-phenyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]silver(I)
(Int Union Crystallography, 2012) Akkurt, Mehmet; Akkoc, Senem; Gok, Yetkin; Dagdemir, Yilmaz; Tahir, Muhammad Nawaz
In the title compound, [AgCl(C24H24N2)], the terminal phenyl and tetramethylbenzene rings [which form a dihedral angle of 87.92 (14)degrees] make dihedral angles of 59.59 (11) and 83.19 (12)degrees with respect to the central benzimidazole ring system. The Ag-C and Ag-Cl single-bond lengths are 2.087 (3) and 2.3267 (9)degrees. The C-Ag-Cl bond angle is 172.84 (7)degrees. C-H center dot center dot center dot pi interactions contribute to the stabilization of the crystal structure. A very weak pi-pi stacking interaction between adjacent tetramethylbenzene rings [centroid-centroid distance = 4.0610 (18) angstrom] is also observed.
Crystal structure of 1,3-bis(4-methylbenzyl)-1H-1,3-benzimidazol-3-ium bromide monohydrate
(Int Union Crystallography, 2015) Celikesir, Sevim Turktekin; Celik, Omer; Akkoc, Senem; Ilhan, Ilhanb Ozer; Gok, Yetkin; Akkurt, Mehmet
In the title hydrated symetrically substituted 1,3-bis(4-methyl-benzyl) benzimidazolium salt, C23H23N2+center dot Br-center dot H2O, the dihedral angles between the benzimidazole ring system (r.m.s. deviation = 0.003 angstrom) and the pendant benzene rings are 73.18 (16) and 77.52 (16)degrees. Both benzene rings lie to the same side of the benzimidazole ring system, giving the cation an overall U-shape. In the crystal, the cation is linked to the water molecule by a short C-H center dot center dot center dot O hydrogen bond and the water molecule forms O-H center dot center dot center dot Br hydrogen bonds. Together, these interactions lead to [010] chains. The packing is consolidated by C-H center dot center dot center dot Br hydrogen bonds and aromatic pi-pi stacking interactions [centroid-centroid distances = 3.5401 (17) and 3.8815 (18) angstrom], generating a three-dimensional network.
Dichlorido(3-chloropyridine-N)[1,3-dialkylbenzimidazol-2-ylidene] palladium(II) complexes: Synthesis, characterization and catalytic activity in the arylation reaction
(Elsevier Science Sa, 2015) Akkoc, Senem; Gok, Yetkin
Six novel Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation (PEPPSI) themed palladium N-heterocyclic carbene (Pd-NHC) complexes (2a-f) were synthesized in good yields from the reaction of 1,3-dialkylbenzimidazolium salts with PdCl2 in the presence of K2CO3 as base in 3-chloropyridine. These synthesized complexes were characterized by means of elemental analysis, FT-IR, H-1 and C-13 NMR spectroscopic methods. The fully characterized novel complexes (2a-f) were tested as catalysts in the direct arylation of 2-n-propylthiazole, 2-n-butylthiophene and 2-n-butylfuran with different aryl bromides at 130 degrees C for 1 h. The complexes exhibited fairly high catalytic activities under the given conditions. The highest conversions were achieved when complexes 2a, 2e and 2f were used as catalysts in direct arylation. (C) 2015 Elsevier B.V. All rights reserved.
Imidazole, pyrimidine and diazepine containing heteroaryl-substituted heterocyclic salts as efficient ligand precursors for Mizoroki-Heck coupling reaction: synthesis, structural characterization and catalytic activities
(Springer, 2014) Gok, Yetkin; Akkoc, Senem; Akkurt, Mehmet; Tahir, Muhammad Nawaz
The nine new heteroaryl-substituted imidazolidinium (1a-c), pyrimidinium (2a-c) and diazepinium (3a-c) salts as N-heterocyclic carbene (NHC) precursors were synthesized in good yields and entirely characterized using elemental analyses and conventional spectroscopic methods. In situ formed complexes from heterocyclic salts (1-3), Pd(OAc)(2) and in the presence of KOBu (t) as a base were tested as catalysts for the Mizoroki-Heck coupling reaction in an aqueous media and very high yields were achieved. 1,3-Di(5-methylthiophen-2-ylmethyl)pyrimidinium hexafluorophosphate salt (2b) was structurally characterized by single-crystal X-ray diffraction. In the 2b compound (C16H21N2S2)(+)[PF6](-), the terminal thiophene rings are twisted with a dihedral angle of 72.8(3)A degrees. In the pyrimidine ring, the three successive C atoms between the N atoms are disordered over two positions [occupancy ratio 0.753(12):0.247(12)]. In the crystal, neighboring molecules are linked by C-HaEuro broken vertical bar F hydrogen bonds, running along the b axis.
In situ Generation of Efficient Palladium N-heterocyclic Carbene Catalysts Using Benzimidazolium Salts for the Suzuki-Miyaura Cross-coupling Reaction
(Bentham Science Publ Ltd, 2016) Akkoc, Senem; Gok, Yetkin; Ilhan, Ilhan Ozer; Kayser, Veysel
Five new unsymmetrically substituted salts containing a benzimidazole backbone were synthesized in high yields and their structures were verified via spectroscopic and analytical methods such as HRMS, 1D and 2D NMR spectroscopy, FT-IR and elemental analysis. The catalytic properties of all the synthesized salts were tested in a homogeneous Suzuki-Miyaura cross-coupling reaction to get coupling products in high efficiencies with low amounts of in situ formed catalysts. In this reaction, the couplings of boronic acid derivatives with different aryl chlorides were made in the presence of palladium acetate, 2-6 and base at various times and temperatures. According to the obtained results, the benzimidazolium salts which are N-heterocyclic carbene (NHC) ligand precursors were found to have high catalytic activity. In particular, the coupling of 4-chlorotoluene with phenylboronic acid was obtained in very high yield and conversion in the catalyzed Pd-NHC complexes which were in situ formed from compounds 3 and 6 and Pd(OAc)(2).
In vitro antimicrobial studies of naphthalen-1-ylmethyl substituted silver N-heterocyclic carbene complexes
(Elsevier, 2019) Gok, Yetkin; Akkoc, Senem; Celikal, Ozlem Ozeroglu; Ozdemir, Ilknur; Gunal, Selami
Seven novel naphthalen-1-ylmethyl substituted silver N-heterocyclic carbene (Ag-NHC) complexes (1-7) were synthesized by the interaction of benzimidazolium salts with silver carbonate in dry dichloromethane at room temperature and characterized by means of spectroscopic methods and elemental analysis techniques. The Ag-NHC compounds were tested for their in vitro antibacterial and antifungal activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Enterococcus faecalis, Candida albicans and Candida tropicalis and showed high antimicrobial activities. The synthesized complexes, in particular, demonstrated better results against both fungi and gram-positive bacteria. (C) 2015 The Authors. Published by Elsevier B.V. on behalf of King Saud University.
In vitro antimicrobial studies of new benzimidazolium salts and silver N-heterocyclic carbene complexes
(Taylor & Francis Ltd, 2016) Gok, Yetkin; Akkoc, Senem; Erdogan, Hulya; Albayrak, Sevil
A series of new benzimidazolium salts (1a-g) were synthesized from the reaction of 1-(4-vinylbenzyl) benzimidazole with various alkyl halides. These salts were used to synthesize silver N-heterocyclic carbene (Ag-NHC) complexes (2a-f). The thirteen compounds were characterized by FT-IR, NMR (H-1 and C-13) spectroscopic methods and an elemental analysis technique. These selected candidates were tested for their in vitro antimicrobial activities. Antibacterial and antifungal results indicated that the new salts, and particularly their silver complexes, were found to be strongly effective against seven Gram (-) bacterial strains, three Gram (+) bacterial strains and one yeast (Candida albicans).
In vitro cytotoxic activities of new silver and PEPPSI palladium N-heterocyclic carbene complexes derived from benzimidazolium salts
(Elsevier Science Sa, 2016) Akkoc, Senem; Ilhan, Ilhan Ozer; Gok, Yetkin; Upadhyay, Parth J.; Kayser, Veysel
New benzimidazolium salts (2, 3) and their silver (4, 5) and palladium (6, 7) N-heterocyclic carbene (Ag-and Pd-NHC) complexes were designed, synthesized and structurally characterized by NMR (H-1 and C-13), IR, HRMS and UV-Vis spectroscopic methods. All the synthesized compounds were tested in human colon cancer (DLD-1), breast cancer (MDA-MB-231) and embryonic kidney (HEK 293T) (non-cancerous) cell lines for in vitro cytotoxicity. Compound 4 specifically showed low IC50 values for these cell lines (IC50 values 12.41 +/- 2.89, 11.98 +/- 2.52 and 4.21 +/- 1.74 mu mol/L in DLD-1, MDA-MB-231 and HEK 293T cell lines, respectively). The Pd-NHC complexes (6, 7) did not exhibit cytotoxic activity (IC50 values > 200 in DLD-1, MDA-MB-231, HEK 293T cell lines). Therefore, Ag-NHC complexes can be further investigated as potential anticancer agents. (C) 2016 Elsevier B. V. All rights reserved.
N- Phenyl- substituted carbene precursors and their silver complexes: synthesis, characterization and antimicrobial activities
(Wiley, 2014) Gok, Yetkin; Akkoc, Senem; Albayrak, Sevil; Akkurt, Mehmet; Tahir, Muhammad Nawaz
A series of unsymmetrically substituted N-heterocyclic carbene (NHC) precursors (1a, 1b, 1c, 1d, 1e) were synthesized from the reaction of N-phenylbenzimidazole with various alkyl halides. These compounds were used to synthesize NHC-silver(I) complexes (2a, 2b, 2c, 2d, 2e). The five new 1-phenyl-3-alkylbenzimidazolium salts (1a, 1b, 1c, 1d, 1e) and their NHC-silver complexes (2a, 2b, 2c, 2d, 2e) were characterized by the H-1 NMR, C-13 NMR and FT-IR spectroscopic methods and elemental analysis techniques. Also, the two NHC-silver complexes 2b and 2c were characterized by single-crystal X-ray crystallography, which confirmed the linear C?Ag?Cl arrangements. The antibacterial activities of the NHC precursor and NHC-silver complexes were tested against three Gram-positive bacterial strains (Bacillus subtilis, Listeria monocytogenes and Staphylococcus aureus) and three Gram-negative bacterial strains (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa) using the microdilution broth method. The NHC-silver complexes showed higher antibacterial activity than the NHC precursors. In addition, silver complexes 2a, 2b, 2c, 2d showed high antibacterial activity against the Gram-positive bacteria L. monocytogenes and S. aureus compared to the standard, tetracycline. Copyright (c) 2014 John Wiley & Sons, Ltd.
N-functionalized benzimidazol-2-ylidene silver complexes: synthesis, characterization, and antimicrobial studies
(Tubitak Scientific & Technological Research Council Turkey, 2013) Gok, Yetkin; Akkoc, Senem; Ozeroglu Celikal, Ozlem; Ozdemir, Ilknur; Gunal, Selami; Sayin, Elif
2-Methoxyethyl, 2-diethylaminoethyl, and 2-phenylethyl-substituted N-heterocyclic carbene (NHC) precursors were treated with Ag2CO3 to yield silver(I)-NHC complexes (1a-g) in dichloromethane as a solvent at room temperature. The 7 new silver-NHC complexes were fully characterized by means of H-1 NMR, C-13 NMR, and elemental analysis techniques. Using the agar dilution procedure recommended by the Laboratory and Clinical Standards Institute, the antimicrobial activities of all the silver-NHC complexes were studied against 2 gram-negative bacterial strains (Pseudomonas aeruginosa and Escherichia coli), 2 gram-positive bacterial strains (Enterococcus faecalis and Staphylococcus aureus), and 2 fungi (Candida tropicalis and Candida albicans).
N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd-NHC complexes: synthesis, characterization and catalytic activity in carbon-carbon bond-forming reactions
(Beilstein-Institut, 2016) Akkoc, Senem; Gok, Yetkin; Ilhan, Ilhan Ozer; Kayser, Veysel
A series of novel benzimidazolium salts (1-4) and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene complexes [ PdCl2(NHC)(Py)] (5-8), where NHC = 1-(N-methylphthalimide)3- alkylbenzimidazolin-2-ylidene and Py = 3-chloropyridine, were synthesized and characterized by means of H-1 and C-13{H-1} NMR, UV-vis (for 5-8), ESI-FTICR-MS (for 2, 4, 6-8) and FTIR spectroscopic methods and elemental analysis. The synthesized compounds were tested in Suzuki-Miyaura cross-coupling (for 1-8) and arylation (for 5-8) reactions. As catalysts, they demonstrated a highly efficient route for the formation of asymmetric biaryl compounds even though they were used in very low loading. For example, all compounds displayed good catalytic activity for the C-C bond formation of 4-tert-butylphenylboronic acid with 4-chlorotoluene.
New compounds based on a benzimidazole nucleus: synthesis, characterization and cytotoxic activity against breast and colon cancer cell lines
(Elsevier Science Sa, 2017) Akkoc, Senem; Kayser, Veysel; Ilhan, Ilhan Ozer; Hibbs, David E.; Gok, Yetkin; Williams, Peter A.; Hawkins, Bryson
Benzimidazolium salts and their Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation (PEPPSI) palladium N-heterocyclic carbene (Pd-NHC) based complexes have been synthesized and their structures characterized with a number of different instrumental techniques including NMR (H-1 and C-13), IR, EI-MS (for 2), X-ray (for 1, 2 and 4) and elemental analysis. The cytotoxicity of all the compounds was tested using the human embryonic kidney (HEK-293T), human breast epithelial adenocarcinoma (MDA-MB-231), and human colon epithelial colorectal adenocarcinoma (DLD-1) cell lines. The benzimidazolium salts (2-5) had more cytotoxic activity against cancerous cells compared with the metal complexes (6-9), which curiously exhibited no activity against any of the cell lines. Based on the IC50 values, compound 5 displayed the highest in vitro anticancer activity among compounds 2-9. Crown Copyright (C) 2017 Published by Elsevier B.V. All rights reserved.
Palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura reactions using naphthalenomethyl-substituted imidazolidin-2-ylidene ligands in aqueous media
(Taylor & Francis Ltd, 2013) Aktas, Aydin; Akkoc, Senem; Gok, Yetkin
Naphthalenomethyl-substituted imidazolidinium salts (1a-g) were prepared and characterized by conventional spectroscopic methods, H-1 NMR, C-13 NMR, FTIR, and elemental analysis techniques. The in situ prepared three component systems naphthalenomethyl-substituted imidazolidinium salts, Pd(OAc)(2), and K2CO3 catalyzed quantitatively the Mizoroki-Heck and Suzuki-Miyaura coupling of aryl halides under mild conditions in aqueous media.

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