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Öğe 2-Hydroxyethyl substituted NHC precursors: Synthesis, characterization, crystal structure and carbonic anhydrase, ?-glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties(Elsevier Science Bv, 2018) Erdemir, Fatos; Celepci, Duygu Barut; Aktas, Aydin; Taslimi, Parham; Gok, Yetkin; Karabiyik, Hasan; Gulcin, IlhamiThis study contains novel a serie synthesis of N-heterocyclic carbene (NHC) precursors that 2-hydroxyethyl substituted. The NHC precursors have been prepared from 1-(2-hydroxyethyl)benzimidazole and alkyl halides. The novel NHC precursors have been characterized by using H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. Molecular and crystal structures of 2a, 2d, 2e, 2f and 2g were obtained with single-crystal X-ray diffraction studies. These novel NHC precursor's derivatives effectively inhibited the a-glycosidase, cytosolic carbonic anhydrase I and II isoforms (hCA I and II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE). Inhibition constant (K-i) were found in the range of 0.30-9.22 nM for alpha-glycosidase, 13.90-41.46 nM for hCA I, 12.82-49.95 nM for hCA II, 145.82-882.01 nM for BChE, and 280.92-1370.01 nM for AChE, respectively. (C) 2017 Elsevier B.V. All rights reserved.Öğe 2-Hydroxyethyl-Substituted (NHC)Pd(II)PPh3 Complexes: Synthesis, Characterization, Crystal Structure and Its Application on Sonogashira Cross-Coupling Reactions in Aqueous Media(Wiley-V C H Verlag Gmbh, 2018) Aktas, Aydin; Celepci, Duygu Barut; Gok, Yetkin; Aygun, MuhittinThis study contains the synthesis of the novel series of the 2- hydroxyethyl substituted Pd-based N-heterocyclic carbene (NHC) / triphenylphosphine (PPh3) complexes. The (NHC)Pd(II)PPh3 complexes have been prepared from the PPh3 ligand, replaced by 3-chloro pyridine ligand in (NHC)Pd(II)(3-Cl-pyridine) complexes. The novel 2-hydroxyethyl substituted (NHC)Pd(II)PPh3 complexes have been characterized by using (HNMR)-H-1, C-13 {H-1}NMR, P-31 {H-1}NMR, FTIR spectroscopy, and elemental analysis techniques. Molecular and crystal structure of 1f was obtained by using single-crystal X-ray diffraction method. The novel 2-hydroxyethyl substituted (NHC)Pd(II)PPh3 complexes have been examined as catalysts in the Sonogashira cross-coupling reactions aqueous medium and demonstrated excellent activity in this reaction.Öğe 2-hydroxyethyl-substituted (NHC)PdI2(pyridine) (Pd-PEPPSI) Complexes: Synthesis, Characterization and the Catalytic Activity in the Sonogashira Cross-coupling Reaction(Wiley-V C H Verlag Gmbh, 2019) Erdemir, Fatos; Celepci, Duygu Barut; Aktas, Aydin; Gok, YetkinHere, new series of the 2-hydroxyethyl-substituted (NHC)PdI2(pyridine) (Pd-PEPPSI) complexes have been synthesized. These complexes have been prepared from the 2-hydroxyethyl-substituted N-heterocyclic carbene (NHC) precursors, palladium chloride and pyridine. The synthesized Pd-PEPPSI complexes have been characterized by using H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. The catalytic activity of the 2-hydroxyethyl-substituted Pd-PEPPSI complexes has been examined in the Sonogashira cross-coupling reaction by using phenylacetylene and aryl bromide. The Pd-PEPPSI complexes have demonstrated great activity in the Sonogashira cross-coupling reaction. The molecular and crystal structures of the three of the Pd-PEPPSI complexes were determined by single-crystal X-ray diffraction method. X-ray studies show that all the molecular structures adopt slightly distorted square-planar geometry around the palladium (II) center.Öğe 2-Hydroxyethyl-Substituted Pd-PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki-Miyaura Reaction for Aryl Chlorides in Aqueous Media(Wiley-V C H Verlag Gmbh, 2018) Aktas, Aydin; Celepci, Duygu Barut; Gok, Yetkin; Aygun, MuhittinIn recent years, PEPPSI (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) complexes have attracted attention in organometallic chemistry. This study contains the synthesis of the 2-hydroxyethyl-substituted Pd-PEPPSI complexes and their catalytic activity in the Suzuki-Miyaura reaction aryl chlorides in aqueous media. The Pd-PEPPSI complexes have been prepared from the 2- hydroxyethyl-substituted N-heterocyclic carbene (NHC) precursors, palladium chloride and 3-chloropyridine. The Pd-PEPPSI complexes have been characterized by using (HNMR)-H-1, (CNMR)-C-13, FTIR spectroscopy and elemental analysis techniques. The Pd-PEPPSI complexes have been examined as catalysts in the Suzuki-Miyaura reactions in aqueous media with arylboronic acid derivatives. Also, they have demonstrated excellent activity in these reactions. Molecular and crystal structure of one of the 2-hydroxyethyl substituted Pd-PEPPSI complex was determined by single crystal X-ray diffraction method. X-ray studies show that the molecular structure adopts a slightly distorted square-planar geometry with the palladium (II) center.Öğe 4-Vinylbenzyl and 2-morpholinoethyl substituted ruthenium (II) complexes: Design, synthesis, and biological evaluation(Elsevier, 2020) Sari, Yakup; Gurses, Canbolat; Celepci, Duygu Barut; Kelestemur, Unzile; Aktas, Aydin; Yuksel, Sengul; Ates, BurhanRecently, the medical applications of organoruthenium complexes have attention attracted to organometallic chemists and biochemists. In this study, 4-vinylbenzyl and 2-morpholinoethyl substituted (NHC) Ru(II)(eta(6)-p-cymene) complexes were synthesized and in vitro DNA binding, cell cytotoxicity (anticancer activity) and genotoxicity properties were determined in order to understand the biological activities. These complexes have been prepared from the 4-vinylbenzyl and 2-morpholinoethyl substituted Ag(I) NHC complexes via transmetallation method. The characterization of the new (NHC)Ru(II)(eta(6)-p-cymene) complexes was performed by using H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. Also, molecular structure of complex 1b was obtained with single-crystal X-ray diffraction method. IC50 value of 1b against MCF-7 cell line was determined as 3.61 mu M and for 1b, an oxidation effect was observed in the concentrations higher than 50 mu g/mL. Comet assay unlike sister chromatid exchange (SCE) analysis data showed correlated results with cytotoxicity as well as DNA binding properties of the complexes. (C) 2019 Elsevier B.V. All rights reserved.Öğe Amine-functionalized benzimidazolium salts: Synthesis, structural characterization, hirshfeld surface analysis and theoretical studies(Elsevier, 2021) Celepci, Duygu Barut; Yigit, Beyhan; Yigit, Murat; Ozdemir, Ismail; Aygun, MuhittinThe benzimidazolium salts were prepared by quaternazition of 1-(2-diisopropylaminoethyl)benzimidazoles in N,N-dimethylformamide with alkyl halides. The salts were characterized spectroscopically and their crystal structures were determined by the single-crystal X-ray diffraction method. The H-1 NMR and C-13 NMR and FT-IR features were also characterized by using Density Functional Theory at B3LYP level with 6-31G* basis set and were compared to the experimental ones. Detailed vibrational assignments of the wavenumbers were performed based on the potential energy distribution (PED) analysis. Quantum chemistry calculations of geometries, electronic properties (FMOs) and reactivity features of the compounds were investigated using the same level of the DFT theory. Natural bond orbital (NBO) analysis was used to analyze the stability of the molecules arising from hyperconjugative interactions and charge delocalization. Global reactivity descriptors were calculated to understand the biological activity behaviors. Additionally, the 3D Hirshfeld surfaces and the associated 2D fingerprint plots were carried out to obtain an insight into the behavior of the interactions in the compounds. A predictive study for the biological activities of the compounds was done using PASS online software and compared to the DFT results. (C) 2021 Elsevier B.V. All rights reserved.Öğe Benzimidazole-functionalized PEPPSI type Pd(II)NHC complexes bearing nitrophenylethyl and hidroxyphenylethyl group: Synthesis, characterization, crystal structure and it's catalytic activity on direct arylation reaction(Elsevier, 2021) Caglilar, Tuba; Behcet, Ayten; Celepci, Duygu Barut; Aktas, Aydin; Gok, Yetkin; Aygun, MuhittinThis study contains synthesis, characterization, crystal structure, and catalytic activity of the new two series PEPPSI (Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation) type Pd(II)NHC complexes nitrophenylethyl and hidroxyphenylethyl groups. All complexes were prepared from the nitrophenylethyl and hidroxyphenylethyl substitute benzimidazolium salts, palladium chloride (PdCl2) and 3-chloropyridine. The structures of all PEPPSI type Pd(II)NHC complexes have been fully characterized by using NMR (H-1 and C-13), FTIR spectroscopic method, and elemental analysis techniques. Also, the single-crystals of four of these complexes were examined by utilizing by the X-ray diffraction method. Also, the catalytic activity of the nitrophenylethyl and hidroxyphenylethyl substituted benzimidazole-functionalized PEPPSI type Pd(II)NHC complexes on the direct arylation reaction were examined. It has been observed that among these complexes, those bearing electron-donor groups (hydroxyphenylethyl) are more active catalysts than those bearing electron-withdrawing groups (nitrophenylethyl) for direct arylation reactions. (C) 2021 Elsevier B.V. All rights reserved.Öğe Design, synthesis, spectroscopic characterizations, single crystal X-ray analysis, in vitro xanthine oxidase and acetylcholinesterase inhibitory evaluation as well as in silico evaluation of selenium-based N-heterocyclic carbene compounds(Taylor & Francis Inc, 2023) Kaya, Guelsen; Noma, Samir Abbas Ali; Celepci, Duygu Barut; Bayil, Imren; Taskin-Tok, Tugba; Gok, Yetkin; Ates, BurhanHerein, eight new NHC-based selenourea derivatives were synthesized and characterized by using spectroscopic method (H-1, F-19, and C-13 NMR, FT-IR), and elemental analysis techniques. These compounds were synthesized by mixing benzimidazolium salts, potassium carbonate, and selenium powder in ethyl alcohol. Additionally, the molecular and crystal structures of the three compounds (1c, 2b, and 2c) were determined using the single-crystal x-ray diffraction (XRD) method. Diffraction analysis demonstrated the partial carbon-selenium double-bond character of these compounds. All compounds were determined to be highly potent inhibitors for AChE and XO enzymes. The IC(50 )values for the compounds were found in the range of 0.361-0.754 mu M for XO and from 0.995 to 1.746 mu M for AChE. The DNA binding properties of the compounds were investigated. These compounds did not have a remarkable DNA binding property. Also, DPPH radical scavenging activities of the compounds were also investigated. Compounds (1c), (2a), (3a), and (3b) exhibited more pronounced DPPH radical scavenging activity when compared to other compounds. Docking studies were applied by using AutoDock 4 to determine interaction mechanism of the selected compounds (1a), (1b), and (3b). The compound (1b) has good binding affinity (-9.78 kcal/mol) against AChE, and (-6.86 kcal/mol) for XO target. Drug similarity properties of these compounds compared to positive controls were estimated and evaluated by ADMET analysis. Furthermore, molecular dynamics simulations have been applied to understand the accuracy of docking studies. These findings and the defined compounds could be potential candidates for the discovery and progress of effective medicine(s) for AChE and XO in the future.In this study, we synthesized selenourea derivatives from N-heterocyclic carbene (NHC) precursors. All compounds were characterized by using NMR, FTIR spectroscopic method, and elemental analysis technique. In addition, the crystal structure of the three compounds was determined using the single-crystal X-ray diffraction method. New selenoura derivatives were tested for their effect to inhibit the xanthine oxidase and acetylcholinesterase enzymes. The DNA binding properties of the Se-NHC compounds were investigated and the compounds did not have significant DNA binding properties. In addition, DPPH radical scavenging activities of Se-NHC compounds were also investigated. All compounds exhibited DPPH radical scavenging activity. Molecular Docking studies using AutoDock 4 were used to determine the interaction mechanism of selected compounds (1a, 1b, and 3b) Drug similarity properties of these compounds compared to positive controls were estimated and evaluated by ADMET analysis. Furthermore, molecular dynamics simulations have been applied to understand the accuracy of docking studies.Öğe Four 2-Hydroxyethyl substituted NHC iodide complexes: structural characterization and theoretical comparisons(Int Union Crystallography, 2018) Celepci, Duygu Barut; Aktas, Aydin; Gok, Yetkin; Aygun, Muhittin[Abstract Not Available]Öğe meta-Cyanobenzyl substituted benzimidazolium salts: Synthesis, characterization, crystal structure and carbonic anhydrase, -glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties(Wiley-V C H Verlag Gmbh, 2018) Turker, Ferhat; Celepci, Duygu Barut; Aktas, Aydin; Taslimi, Parham; Gok, Yetkin; Aygun, Muhittin; Gulcin, Ilhamimeta-Cyanobenzyl-substituted N-heterocyclic carbene (NHC) precursors were synthesized by the reaction of a series of N-(alkyl)benzimidazolium with 3-bromomethyl-benzonitrile. These benzimidazolium salts were characterized by using H-1 NMR, C-13 NMR, FTIR spectroscopy, and elemental analysis techniques. The molecular and crystal structures of 2f and 2g complexes were obtained by using the single-crystal X-ray diffraction method. The derivatives of these novel NHC precursors were effective inhibitors of -glycosidase (AG), the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), butyrylcholinesterase (BChE), and acetylcholinesterase (AChE) with K-i values in the range of 1.01-2.12nM for AG, 189.56-402.44nM for hCA I, 112.50-277.37nM for hCA II, 95.45-352.58nM for AChE, and 132.91-571.18nM for BChE. In the last years, inhibition of the CA enzyme has been considered as a promising factor for pharmacologic intervention in a diversity of disturbances such as obesity, glaucoma, cancer, and epilepsy.Öğe Mixed phosphine/N-heterocyclic carbene-palladium complexes: synthesis, characterization, crystal structure and application in the Sonogashira reaction in aqueous media(Springer, 2019) Aktas, Aydin; Erdemir, Fatos; Celepci, Duygu Barut; Gok, Yetkin; Aygun, MuhittinA series of 2-hydroxyethyl-substituted N-heterocyclic carbene-(NHC)PdX2PPh3 complexes have been synthesized by substitution of the pyridine or 3-chloropyridine ligand in (NHC)PdX2(pyridine/3-chloropyridine) complexes with triphenylphosphine. The new complexes were characterized by H-1, C-13 {H-1}, P-31 {H-1}NMR, FTIR spectroscopy and elemental analysis. Also, the molecular and crystal structures of 1c and 1d have been obtained by single-crystal X-ray diffraction. The 2-hydroxyethyl-substituted (NHC)PdX2PPh3 complexes have been examined as catalysts for the Sonogashira cross-coupling reaction in water/DMF solvent mixtures.Öğe New (NHC)Pd(II)(PPh3) complexes: synthesis, characterization, crystal structure and its application on Sonogashira and Mizoroki-Heck cross-coupling reactions(Springer International Publishing Ag, 2020) Erdemir, Fatos; Aktas, Aydin; Celepci, Duygu Barut; Gok, YetkinIn this study, new six Pd-based complexes containing mixture N-heterocyclic carbene (NHC) and triphenylphosphine-(PPh3) ligands were synthesized from the reaction of the (NHC)PdI2(pyridine) with-PPh3. The new (NHC)PdI2(PPh3) complexes were characterized using FTIR, H-1-NMR, C-13-NMR, and P-31-NMR spectroscopy and elemental analyses techniques. These spectra are consistent with the proposed formula. Molecular and crystal structure of two complexes was obtained using single-crystal X-ray diffraction method. Based on the crystal results, a cis geometry was assigned to all the complexes. These new complexes have been examined as the catalyst in the Sonogashira cross-coupling reaction. The catalytic conversions of the complexes were obtained between 71 and 99% from the reaction of phenylacetylene and aryl bromides. Also, these new complexes have been examined as the catalyst in the Mizoroki-Heck cross-coupling reaction. The catalytic conversions of the complexes were obtained between 80 and 100% from the reaction of styrene and aryl bromides.Öğe New 2-hydroxyethyl substituted N-Heterocyclic carbene precursors: Synthesis, characterization, crystal structure and inhibitory properties against carbonic anhydrase and xanthine oxidase(Elsevier Science Bv, 2019) Aktas, Aydin; Noma, Samir Abbas Ali; Celepci, Duygu Barut; Erdemir, Fatos; Gok, Yetkin; Ates, BurhanHere, the synthesis, spectral and the structural studies of 2-hydroxyethyl substituted N-heterocyclic carbene (NHC) precursors and the enzyme inhibition activities of the NHC precursors were investigated against the cytosolic carbonic anhydrase I and II isoenzymes (hCA I and hCA II), and xanthine oxidase (XO). The IC50 values of NHC precursors against these enzymes were determined by spectrophotometric method. The spectra of new NHC precursors have been obtained by using H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. The structure of a new NHC precursor was established by using single-crystal X-ray diffraction method. The results of inhibition experiment indicated that all 2-hydroxyethyl substituted NHC derivatives showed remarkable inhibition activity toward hCA I, hCA II and XO. The range of IC50 values for hCA I, hCA II and XO inhibition was determined as 0.1565-0.5127, 0.1524-0.5368 and 1.253-5.342 mu M. Especially, trimethylbenzyl derivative of 2-hydroxyethyl substituted NHC precursor has demonstrated high inhibition effect on all studied enzymes due to steric bulk of this substituent. (C) 2019 Elsevier B.V. All rights reserved.Öğe New morpholine-liganded palladium(II) N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, and DNA-binding studies(Wiley-V C H Verlag Gmbh, 2019) Turker, Ferhat; Gurses, Canbolat; Celepci, Duygu Barut; Aktas, Aydin; Ates, Burhan; Gok, YetkinA series of the morpholine-liganded palladium(II) complexes (1a-e) bearing N-heterocyclic carbene (NHC) functionalized by benzonitrile were synthesized. These complexes were synthesized from (NHC)Pd(II)(pyridine) complexes (PEPPSI) and morpholine. The new complexes were fully characterized by using H-1 NMR, C-13 NMR, Fourier-transform infrared spectroscopy, and elemental analysis techniques. Single-crystal X-ray diffraction was used to determine the structure of a derivative. The DNA-binding studies of the new (NHC)Pd(II)morpholine complexes were examined using the pBR322 plasmid. The 2,4,6-trimethylbenzyl derivative compound has the most DNA binding activity. In addition, for the 3-methylbenzyl derivative compound, oxidation effects were observed at concentrations higher than 100 mu g/ml. Also, the molecular and crystal structures of the complex 3-methylbenzyl derivative compound were recorded by using a single-crystal X-ray diffraction method.Öğe New Pd-PEPPSI complexes bearing meta-cyanobenzyl-Substituted NHC: Synthesis, characterization, crystal structure and catalytic activity in direct C-H arylation of (Hetero)arenes with aryl bromides(Elsevier, 2020) Turker, Ferhat; Bereket, Imran; Celepci, Duygu Barut; Aktas, Aydin; Gok, YetkinThe prestige of the PEPPSI (Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation) complexes in organometallic chemistry is increasing day by day. Herein, the well-defined seven meta-cyanobenzyl-substituted N-heterocyclic carbene (NHC)-Pd(II)-pyridine (Pd-PEPPSI) complexes were synthesized using palladium acetate, which unlike general procedure is a more economical method than palladium chloride. The new Pd-PEPPSI complexes were obtained from the reaction of the cyanobenzyl substituted NHC precursors and palladium acetate in pyridine. The new complexes have been fully characterized by H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. Also, the X-ray diffraction method was used to determine the single-crystal structure of a complex. The Pd-PEPPSI complexes have been examined as catalysts in the direct arylation reactions of 2-n-butylfuran and 2-n-butylthiophene with aryl bromide. All complexes have demonstrated excellent activity in these reactions. The Molecular and crystal structure of one of the cyanobenzyl substituted Pd-PEPPSI complexes was determined by the single-crystal X-ray diffraction method. X-ray diffraction studies show that the molecular structure adopts a slightly distorted square-planar geometry with the palladium (II) center. (c) 2019 Elsevier B.V. All rights reserved.Öğe Novel 2-aminopyridine liganded Pd(II) N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure and bioactivity properties(Academic Press Inc Elsevier Science, 2019) Erdemir, Pato; Celepci, Duygu Barut; Aktas, Aydin; Gok, Yetkin; Kaya, Ruya; Taslimi, Parham; Demir, YelizIn this work, the synthesis, crystal structure, characterization, and enzyme inhibition effects of the novel a series of 2-aminopyridine liganded Pd(II) N-heterocyclic carbene (NHC) complexes were examined. These complexes of the Pd-based were synthesized from PEPPSI complexes and 2-aminopyridine. The novel complexes were characterized by using C-13 NMR, H-1 NMR, elemental analysis, and FTIR spectroscopy techniques. Also, crystal structures of the two compounds were recorded by using single-crystal X-ray diffraction assay. Also, these complexes were tested toward some metabolic enzymes like a-glycosidase, aldose reductase, butyrylcholinesterase, acetylcholinesterase enzymes, and carbonic anhydrase I, and II isoforms. The novel 2-aminopyridine liganded (NHC) PdI2(2-aminopyridine) complexes (1a-i) showed Ki values of in range of 5.78 +/- 0.33-22.51 +/- 8.59 nM against hCA I, 13.77 +/- 2.21-30.81 +/- 4.87 nM against hCA II, 0.44 +/- 0.08-1.87 +/- 0.11 nM against AChE and 3.25 +/- 0.34-12.89 +/- 4.77 nM against BChE. Additionally, we studied the inhibition effect of these derivatives on aldose reductase and alpha-glycosidase enzymes. For these compounds, compound 1d showed maximum inhibition effect against AR with a Ki value of 360.37 +/- 55.82 nM. Finally, all compounds were tested for the inhibition of alpha-glycosidase enzyme, which recorded efficient inhibition profiles with Ki values in the range of 4.44 +/- 0.65-12.67 +/- 2.50 nM against aglycosidase.Öğe Novel 2-hydroxyethyl substituted N-coordinate-Pd(II)(NHC) and bis(NHC)Pd(II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction(Indian Acad Sciences, 2019) Aktas, Aydin; Celepci, Duygu Barut; Gok, YetkinThe direct arylation reaction has attracted attention in recent years especially because of its environment-friendly properties. In this study, we researched the synthesis of 2-hydroxyethyl substituted bis(NHC)Pd(II) complexes and also the synthesis of N-coordinate-Pd(II)(NHC) complexes containing N-bound benzimidazolium from palladium acetate ([Pd(CH3COO)(2)]) with 1,3-disubstituted benzimidazolium halides in DMSO. All the complexes have been characterized by using H-1 NMR, C-13 NMR, FTIR spectroscopy and elemental analysis techniques. The molecular and crystal structure of one of the complexes is confirmed by using single-crystal X-ray diffraction. These complexes have been examined as the catalyst in the direct arylation reaction with 2-n-butylfuran and 2-n-butylthiophene and have demonstrated excellent activity in this reaction.Öğe Novel Benzylic Substituted Imidazolinium, Tetrahydropyrimidinium and Tetrahydrodiazepinium Salts: Potent Carbonic Anhydrase and Acetylcholinesterase Inhibitors(Wiley-V C H Verlag Gmbh, 2018) Yigit, Beyhan; Yigit, Murat; Celepci, Duygu Barut; Gok, Yetkin; Aktas, Aydin; Aygun, Muhittin; Taslimi, ParhamThe new imidazolinium, tetrahydropyrimidinium and tetrahydrodiazepinium salts were synthesized in good yield by the reaction of the corresponding N,N'-dialkylalkanediamine with triethyl orthoformate in the presence of ammonium chloride. All of the compounds were obtained, and spectroscopically characterized. The crystal structure for the 1,3-bis(4-benzyloxy-3-methoxybenzyl)-3,4,5,6-tetrahydropyrimidinium chloride (5g) was determined by single-crystal X-ray diffraction. The biological properties of all novel compounds were tested and the influence of ring size and benzylic N-substituents on the biological activities were examined. Also, they were found as effective inhibitors against cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) enzyme. Among these compounds, 1,3-bis(4-(1-piperidinyl)benzyl)-3,4,5,6-tetrahydropyrimidinium chloride (5f) demonstrated the the best inhibition effects against hCA I, 1,3-bis(4-benzyloxy-3-methoxybenzyl)-3,4,5,6-tetrahydropyrimidinium chloride (5g) demonstrated the the best inhibition effects against cytosolic hCA II isoenzyme. On the other hand, 1,3-Bis(4-methylthiobenzyl)-3,4,5,6-tetrahydropyrimidinium chloride, (5e) demonstrated the the best inhibition effects against AChE enzyme.Öğe Novel morpholine liganded Pd-based N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, antidiabetic and anticholinergic properties(Pergamon-Elsevier Science Ltd, 2019) Aktas, Aydin; Celepci, Duygu Barut; Kaya, Ruya; Taslimi, Parham; Gok, Yetkin; Aygun, Muhittin; Gulcin, IlhamiThis study involves the synthesis of novel N-heterocyclic carbene (NHC)PdX2(morpholine) complexes (1a-i). These Pd-based complexes are synthesized from pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) complexes and morpholine. The new complexes were characterized by spectroscopy (IR, H-1 and C-13 NMR) techniques. Also, the crystal structures of lb and if were obtained by utilizing the single-crystal X-ray diffraction method. The synthesized compounds in this study were investigated for their inhibition action against equin serum butyrylcholinesterase (BChE) and Electrophorus electricus acetylcholinesterase (AChE) as the capability drug aims for Alzheimer's disease (AD). These novel morpholine liganded Pd-based N-heterocyclic complexes were good inhibitors of BChE, alpha-glycosidase, cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and AChE, with K-i values in the range of 10.77 +/- 1.01-45.86 +/- 5.65 mu M for hCA I, 25.42 +/- 5.18-57.82 +/- 3.01 mu M for hCA II, 12.26 +/- 3.32-50.36 +/- 6.19 mu M for a-glycosidase, 9.97 +/- 1.26-60.75 +/- 15.98 M for BChE, and 10.28 1.55-30.12 3.22 M for AChE. The inhibition of the alpha-glycosidase enzyme, an important carbohydrate hydrolyzing catalyst, could be used as one of the efficient methodologies in both treating and preventing diabetes by controlling the suppressing postprandial hyperglycemia and postprandial glucose amounts. (C) 2018 Elsevier Ltd. All rights reserved.Öğe Novel PEPPSI-type N-heterocyclic carbene palladium(II) complexes: Synthesis, characterization, in silico studies and enzyme inhibitory properties against some metabolic enzymes(Elsevier Science Sa, 2023) Yigit, Beyhan; Taslimi, Parham; Celepci, Duygu Barut; Taskin-Tok, Tugba; Yigit, Murat; Aygun, Muhittin; Ozdemir, IsmailIn this study, a series of PEPPSI-type N-heterocyclic carbene palladium(II) complexes 3a-e were synthesized using amine functionalized benzimidazolium salts 2a-e as N-heterocyclic carbene precursors. These complexes were characterized by FT-IR, 1H NMR and 13C NMR spectroscopy, elemental analysis and mass spectrometry. Also, the molecular and crystal structure of 3b has been determined by the single-crystal X-ray diffraction method. According to the structural analysis, the geometry of the palladium center of the complex adopts a slightly distorted square planar environment. The benzimidazolium salts 2a-e and their palladium(II) complexes 3a-e were screened for human carbonic anhydrase I, II (hCAs I and II), and alpha-glycosidase inhibitory activities. Results indicated that all the synthetic compounds exhibited potent inhibitory activities against all targets as compared to the standard inhibitors, revealed by IC50 values. Ki values of 2a-e and 3a-e for hCA I, hCA II, and alpha-glycosidase enzymes were obtained in the ranges 1.17 +/- 0.11-65.50 +/- 8.20 mu M, 1.02 +/- 0.08-57.60 +/- 6.41 mu M, and 118.86 +/- 11.92-509.21 +/- 26.61 nM, respectively. Besides these, molecular docking calculations of potent compounds 2b, 2d, 2e, 3a, 3b, 3c and 3e towards human carbonic anhydrase I (hCA I), human carbonic anhydrase II (hCA II), and alpha-glycosidase (alpha-Gly) were presented using AutoDock 4. Among the compounds discussed, compounds 3c, 3a, 2e and 2b have the best binding affinity for alpha-Gly (-9.87,-9.77,-9.04 and-8.63 kcal/mol); compounds 3e, 3b, 2d and 2e turn out to have the second-best binding affinity (-8.80,-8.74,-8.39 and-7.57 kcal/mol) against hCA II. Lastly, compounds showing the lowest binding affinity for hCA I enzyme are 3e, 3b, 2d and 2e, respectively. These findings show that especially NHC-palladium(II) complexes 3a-e are more active for all three enzyme structures than their N-heterocyclic carbene precursors 2a-e and may be potential candidates for the discovery and development of effective inhibitors for the related enzymes in the future.
