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Öğe 1,3-Bis(3-phenylpropyl)-1H-1,3-benzimidazole-2(3H)-selone(Wiley-Blackwell, 2011) Akkurt, Mehmet; Yilmaz, Ulku; Kucukbay, Hasan; Buyukgungor, OrhanThe title molecule, C25H26N2Se, has mirror symmetry, with the mirror plane passing through the atoms of the C=Se bond and the mid-points of the two C-C bonds of the benzene ring of the benzimidazole group. The dihedral angle between the benzimidazole ring system and the phenyl ring is 71.62 (14)degrees.Öğe 1,3-Bis(3-phenylpropyl)-1H-benzimidazol-3-ium-2-carbodithioate(Wiley-Blackwell Publishing, Inc, 2009) Akkurt, Mehmet; Yilmaz, Ulku; Kucukbay, Hasan; Gencaslan, Mustafa; Buyukgungor, OrhanThe title compound, C(26)H(26)N(2)S(2), was synthesized from bis[1,3-bis(3-phenylpropyl)benzimidazolidine-2-ylidene] and CS(2) in toluene. The molecular structure is composed of a benzimidazole ring system with two phenylpropyl substituents and a dithiocarboxylate group in the 2-position. The benzimidazole unit is essentially planar, with a maximum atomic deviation of 0.008 (2) angstrom, and makes dihedral angles of 72.72 (10) and 27.62 (12)degrees, with the two phenyl rings. The dihedral angle between the two phenyl rings is 55.98 (15)degrees. The molecular packing is stabilized by a C-H center dot center dot center dot S intermolecular hydrogen-bonding interaction and a C-H center dot center dot center dot pi interaction between a benzene H atom and the phenyl ring of a neighbouring molecule.Öğe 1,3-Bis(3-phenylpropyl)-1H-benzimidazole-2(3H)-tellurone(Blackwell Publishing, 2008) Yalcin, Serife Pinar; Akkurt, Mehmet; Yilmaz, Uelkue; Kucukbay, Hasan; Buyukgungor, OrhanThe title compound, C25H26N2Te, was synthesized from bis[1,3-bis(3-phenylpropyl)benzimidazolidin-2-ylidene] and Te in a toluene solution. The molecule possesses a twofold rotation axis passing through the Te atom and the center of the benzimidazole ring system. The benzimidazole ring system makes an angle of 67.9 (4) with the phenyl rings.Öğe 1,3-bis(3-phenylpropyl)benzimidazolium bromide monohydrate(Int Union Crystallography, 2008) Akkurt, Mehmet; Karaca, Selvi; Yilmaz, Ulku; Kucukbay, Hasan; Buyukgungor, OrhanIn the title compound, C25H27N2+center dot Br-center dot H2O, the benzimidazole unit is essentially planar, with a maximum deviation of 0.020 (6) angstrom. The benzimidazole unit makes dihedral angles of 83.6 (3) and 81.0 (3)degrees with the two terminal phenyl rings. The dihedral angle between the phenyl rings is 58.5 (4)degrees. In the crystal structure, there are C-H center dot center dot center dot O hydrogen bonds, a C H center dot center dot center dot pi interaction between a phenyl H atom and the phenyl ring of a neighbouring molecule, and pi-pi interaction [3.512 (3) angstrom] between the centroids of the five-membered ring and the benzene ring of the benzimidazole unit of an adjacent molecule.Öğe 1,3-Difurfurylbenzimidazolium chloride monohydrate(Wiley-Blackwell, 2009) Akkurt, Mehmet; Sireci, Nihat; Deniz, Selma; Kucukbay, Hasan; Buyukgungor, OrhanThe title compound, C17H15N2O2+center dot Cl-center dot H2O, was synthesized from benzimidazole and furfryl chloride in dimethylformamide. The cationic benzimidazolium ring is connected to two furan rings via methylene bridges. The furan rings make dihedral angle of 79.09 (18)degrees with respect to each other, and make dihedral angles of 73.92 (12) and 72.58 (13)degrees with respect to the benzimidazole ring. O-H center dot center dot center dot Cl, C-H center dot center dot center dot O and C-H center dot center dot center dot Cl hydrogen bonds and C-H center dot center dot center dot pi interactions contribute to the stabilization of the crystal structure. Furthermore, there is a pi-pi interaction between adjacent five- and six-membered rings of the benzimidazole groups [centroid-centroid distance = 3.5305 (8) angstromÖğe 1-(Prop-2-en-1-yl)-3-[(trimethylsilyl)methyl]benzimidazolium bromide monohydrate(Int Union Crystallography, 2010) Baktir, Zeliha; Akkurt, Mehmet; Sireci, Nihat; Kucukbay, HasanIn the title compound, C14H21N2Si+center dot Br-center dot H2O, the benzimidazole ring system is almost planar [maximum deviation = 0.021 (2) angstrom]. In the crystal, O-H center dot center dot center dot Br and C-H center dot center dot center dot O hydrogen bonds link the ions via the O atoms of the water molecules. In addition, there are pi-pi stacking interactions between the centroids of the benzene and imidazole rings of the benzimidazole ring system [centroid-centroid distances = 3.521 (3) and 3.575 (2) angstrom].Öğe 1-Benzyl-3-[(trimethylsilyl)methyl]benzimidazolium chloride monohydrate(Wiley-Blackwell, 2010) Akkurt, Mehmet; Celik, Ismail; Kucukbay, Hasan; Sireci, Nihat; Buyukgungor, OrhanThe title compound, C(18)H(23)N(2)Si(+)center dot Cl(-)center dot H(2)O, was synthesized from 1-[(trimethylsilyl)methyl]benzimidazole and benzyl chloride in dimethylformamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) angstrom, and makes an angle of 74.80 (12)degrees with the phenyl ring. The crystal packing is stabilized by O-H center dot center dot center dot Cl, C-H center dot center dot center dot Cl, C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions between symmetry-related molecules together with pi-pi stacking interactions between the imidazolium and benzene rings [centroid-centroid distance = 3.5690 (15) angstrom] and between the benzene rings [centroid-centroid distance = 3.7223 (14) angstrom].Öğe 1-cyclohexylmethyl-3-methyl-2-[(phenyl-imino)(sulfido)methyl]benzimidazolium(Int Union Crystallography, 2008) Akkurt, Mehmet; Karaca, Selvi; Kucukbay, Hasan; Sireci, Nihat; Buyukgungor, OrhanIn the zwitterionic title compound, C22H25N3S, the benzimidazole ring system makes a dihedral angle of 55.69 (11) degrees with the phenyl ring. In the crystal structure, inter- and intramolecular C-H center dot center dot center dot S interactions occur.Öğe 1-{[Dimethyl(phenyl) silyl] methyl}-3-(2-phenylethyl)-1H-benzimidazol-3-ium bromide monohydrate(Int Union Crystallography, 2012) Akkurt, Mehmet; Kucukbay, Hasan; Sireci, Nihat; Buyukgungor, OrhanThe title compound, C24H27N2Si+center dot Br-center dot H2O, was synthesized from 1-(dimethylphenylsilylmethyl)-1H-benzimidazole and (2-bromoethyl) benzene in dimethylformamide. The benzimidazole ring system is nearly planar, with a maximum deviation of 0.015 (5) angstrom, and forms dihedral angles of 73.0 (3) and 39.6 (2)degrees, with the phenyl rings. In the crystal, molecules are linked by O-H center dot center dot center dot Br, C-H center dot center dot center dot Br and C-H center dot center dot center dot O hydrogen bonds. In addition, the structure features pi-pi stacking interactions, with a face-to-face separation of 3.644 (3) angstrom between parallel benzimidazole ring systems.Öğe Anticancer, antioxidant, DFT calculations, and docking studies of some new peptide-indole conjugates(Acg Publications, 2024) Kucukbay, Hasan; Gonul, Zeynep; Kurucay, Ali; Ates, Burhan; Boulebd, Houssem; Kucukbay, F. ZehraIn this study, the structures of six new peptide-indole derivatives were elucidated through spectroscopic and analytical methods following their synthesis. In addition to their anticancer and antioxidant properties, density functional theory (DFT) calculations and docking studies were conducted for the compounds. According to the obtained results, compounds 1 and 3 were identified as the most active against the MCF-7 cell line, with IC50 values of 8.72 and 5.86 mu g/mL, respectively. Conversely, compounds 4 and 1 were found to be the most active against the A549 cell line, with IC50 values of 15.43 and 16.10 mu g/mL, respectively. When compared to standard antioxidants using both the DPPH and iron reduction power assays, the compounds did not exhibit significant antioxidant activity. The molecular geometry and electronic properties of the synthesized peptide-indole derivatives were investigated through theoretical calculations using the Density Functional Theory (DFT) method. Molecular docking studies were also conducted to investigate the binding modes of the synthesized compounds within the active sites of EGFR enzyme.Öğe Antioxidant and cytotoxic properties of some new dipeptide-indole conjugates(Wiley, 2023) Gonul, Zeynep; Ozturk, Dilara Altay; Kucukbay, Fatumetuzzehra; Tekin, Suat; Tekin, Zehra; Kucukbay, HasanIn this study, 10 new indole-dipeptide conjugates were synthesized, and their anticancer activity was determined against on A2780 (ovarian cancer cell line) and MCF-7 (breast cancer cell line) cells. Among compounds, 5 and 10 showed better activity against A2780 cell lines than the standard drug docatexel at 0.1 and 1 mu M concentrations, while only compound 5 showed better activity than docatexel, the MCF-7 cell line at 0.1 and 1 mu M concentrations. The antioxidant potencies of the compounds were low in both the DPPH and iron reducing power methods tested when compared to standard antioxidants used in this work.Öğe Benzimidazole based a new therapeutic agent effective on ovarian cancer cells(Wiley-Blackwell, 2015) Tekin, Suat; Mumcu, Akin; Kucukbay, Hasan; Sandal, Suleyman[Abstract Not Available]Öğe Benzyl {2-[(2-(1H-Benzo[d][1,2,3]triazol-1-yl)-2-oxoethyl)amino]-2-oxoethyl} carbamate(Mdpi, 2014) Kucukbay, Hasan; Bugday, NesrinN-(Protected alpha-aminoacyl) benzotriazoles are powerful acylating agents, and they are used frequently for preparing peptides and their mimetics and conjugates. The present paper describes the synthesis and characterization of a new benzyl {2-[(2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-oxoethyl)amino]-2-oxoethyl} carbamate.Öğe Concentration effects of some new benzimidazole derivatives on Human Breast Cancer Cell Viability(Wiley-Blackwell, 2015) Tekin, Suat; Mumcu, Akin; Kucukbay, Hasan; Sandal, Suleyman[Abstract Not Available]Öğe Crystal Structure of Dichloridobis[5-nitro-1-trimethylsilylmethyl-1H-benzimidazole-?N3] cobalt (II) N,N-dimethylformamide solvate.(Int Union Crystallography, 2010) Yalcin, Serife Pinar; Akkurt, Mehmet; Sireci, Nihat; Kucukbay, Hasan; Tahir, M. Nawaz[Abstract Not Available]Öğe Cytotoxic and antimicrobial potential of benzimidazole derivatives(Wiley-V C H Verlag Gmbh, 2021) Kucukbay, Hasan; Uckun, Mustafa; Apohan, Elif; Yesilada, OzferNew benzimidazole derivatives were synthesized and their structures were characterized by spectroscopic and microanalysis techniques. The cytotoxic properties of ten benzimidazole derivatives, five of which were synthesized in our previous studies, were determined against the lung cancer cell line, A549, and the healthy lung epithelial cell line, BEAS-2B. Among the ten compounds tested, based on the 72-h incubation results, compound 12 was the most cytotoxic against the A549 cell line, whereas against the BEAS-2B cell line, it was as cytotoxic as cisplatin. The IC50 values of compound 12 were 3.98 and 2.94 mu g/ml for A549 and BEAS-2B cells, respectively. The cisplatin values were 6.75 and 2.75 mu g/ml for A549 and BEAS-2B cells, respectively. Compounds 10, 8, 7, and 13 showed toxic effects against A549 cells, but were less toxic against BEAS-2B cells than cisplatin. The antimicrobial activity of these compounds against pathogenic bacteria and yeasts was also evaluated based on their minimum inhibitory concentration (MIC) values. The compounds, except 12 and 13, generally showed higher antimicrobial activity against yeasts, compared with bacteria. Compound 12 showed better activity against Pseudomonas aeruginosa and Staphylococcus aureus than against Escherichia coli. Compounds 7, 8, and 11 were the most effective ones against the microorganisms, and yeasts were highly sensitive to these compounds with MIC values of 25-100 mu g/ml.Öğe Cytotoxic potential of silver, palladium, rhodium, ruthenium, and iridium complexes of a cycloheptyl-substituted lipophilic N-heterocyclic carbene ligand(Taylor & Francis Ltd, 2023) Karatas, Mert Olgun; Sekerci, Guldeniz; Tekin, Suat; Sandal, Suleyman; Kucukbay, HasanLipophilicity is a crucial parameter for cytotoxicity of metal complexes, in many cases associated with increased activity. In the present study, we synthesized a series of N-heterocyclic carbene (NHC) complexes of different metals with a lipophilic benzimidazolium chloride to investigate and compare their cytotoxicity. Rh- (4), Ru- (5), and Ir-NHC (6) complexes of a cycloheptyl-substituted benzimidazole-based NHC ligand (1) have been prepared by transmetalation reaction between Ag-NHC and the corresponding metal compound. The newly synthesized complexes have been characterized by NMR, IR, LC-MS spectroscopy, and elemental analyses. The anti-growth effects of the newly synthesized Rh-, Ru-, and Ir-NHC complexes and previously reported NHC precursor (1), Ag- (2), and Pd-NHC (3) complexes against human breast (MCF-7), colorectal (Caco-2), ovarian (A2780), and prostate (LNCaP) cancer cell lines have been investigated by MTT assay. The results revealed that the compounds provide stronger anti-growth effects against all cell lines compared to standard drug cisplatin. Among the compounds, benzimidazolium chloride, and Ag-NHC complex showed promising activities.Öğe Determination of pKa values of some novel benzimidazole salts by using a new approach with 1H NMR spectroscopy(Wiley-Blackwell, 2015) Mumcu, Akin; Kucukbay, HasanBenzimidazoles and their derivatives including imidazole are studied widely because they exist in the structure of natural products and different drugs. pK(a) values are extremely important for drug discovery and improvement in order to determine pharmacokinetic and pharmacodynamic features such as permeation through biological barriers, interactions with the target area or side effects. Acid-base features (pK(a)) have great importance not only for physiological characteristics but also for being used as a ligand or changing physico-chemical features by turning benzimidazoles into salts. Within the scope of this study, a variety of new benzimidazole salts were synthesized, and their characterizations were made by NMR spectroscopy, FTIR spectroscopy and element analysis techniques. The pK(a) values of synthesized benzimidazole saltswere determined by inflection point approach using integration values obtained with H-1 NMR spectroscopy and Henderson-Hasselbalch analysis. pK(a) values of some benzimidazole salts were also determined by potentiometric methods in order to compare those of NMR spectroscopy results. Copyright (C) (C) 2015 John Wiley & Sons, Ltd.Öğe Dichloridobis[5-nitro-1-trimethylsilylmethyl-1H-benzimidazole-?N3]cobalt(II) N,N-dimethylformamide solvate(Int Union Crystallography, 2010) Akkurt, Mehmet; Yalcin, Serife Pinar; Sireci, Nihat; Kucukbay, Hasan; Tahir, M. NawazThe title compound, [CoCl2(C11H15N3O2Si)(2)]center dot C3H7NO, was synthesized from 5-nitro-1-trimethylsilylmethyl-1H-benzimidazole and cobalt(II) chloride in dimethylformamide. The Co-II atom is coordinated in a distorted tetrahedral environment by two Cl atoms and two N atoms. In the crystal structure, there are a number of C-H center dot center dot center dot Cl and C-H center dot center dot center dot O hydrogen-bonding interactions between symmetry-related molecules.Öğe Effects of new NHC derivatives as ligands in the Suzuki-Miyaura reaction(Taylor & Francis Inc, 2021) Yilmaz, Ulku; Kucukbay, HasanA series of NHC-derivative ligands was synthesized from bisbenzimidazole salts as the precursor of N-heterocyclic carbene with chalcogens, carbon disulfide, and phenyl isothiocyanate reagents. These new ligands were used in the Suzuki-Miyaura cross-coupling reaction in the presence of palladium(II) acetate. Particularly, it was observed a remarkable ligand activity with tellurourea (5).
