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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, Muhittin
This 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.
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, Muhittin
In 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.
2-Morpholinoethyl-substituted N-heterocyclic carbene (NHC) precursors and their silver(I)NHC complexes: synthesis, crystal structure and in vitro anticancer properties
(Springer, 2018) Aktas, Aydin; Kelestemur, Unzile; Gok, Yetkin; Balcioglu, Sevgi; Ates, Burhan; Aygun, Muhittin
In this study, a series of unsymmetrically 2-morpholinoethyl-substituted benzimidazolium salts and their Ag(I)NHC complexes were synthesized. The 1,3-dialkylbenzimidazolium salts (1a-d) were synthesized in dimethylformamide at 80 A degrees C temperature from the N-(2-morpholinoethyl)benzimidazole and alkyl halides. The Ag(I)NHC complexes (2a-d) were synthesized in dichloromethane at room temperature from the benzimidazolium salts and Ag2O. All compounds were characterized by spectroscopic techniques (NMR and FT-IR) and elemental analyses. Also, the salt 1c and complex 2c were characterized by single-crystal X-ray crystallography. Anticancer activities of 2-morpholinoethyl-substituted benzimidazolium salts and Ag(I)NHC complexes were investigated against the MCF-7 breast cancer cell line, and the IC30 and IC50 values of these compounds were found to be in the range of 241-490 and 6-14 A mu M, respectively.
5(6)-Benzoyl-Substituted Benzimidazoles and Their Benzimidazolium Salts: Design, Synthesis, Characterization, Crystal Structure, and Some Metabolic Enzymes Inhibition Properties
(Wiley-V C H Verlag Gmbh, 2025) Aktas, Aydin; Ozden, Eda Mehtap; Celepci, Duygu Barut; Taskin-Tok, Tugba; Ekti, Funda Sultan; Gulcin, Ilhami; Aygun, Muhittin
Herein, the synthesis of 1-alkyl-5(6)-benzoyl-substituted benzimidazoles and their 1,3-bisalkylbenzimidazolium halide salts are presented and evaluated for some metabolic enzyme inhibition. All compounds were characterized using various spectroscopic techniques. Single-crystal XRD analysis was performed to determine the molecular structure of two compounds. The newly synthesized compounds exhibited significant inhibitory effects against acetylcholinesterase (AChE) and human carbonic anhydrase isoforms I and II (hCA I and hCA II) enzymes. These compounds demonstrated promising inhibition profiles, with Ki values ranging from 12.4 +/- 5.4 to 109.4 +/- 49.9 nM for hCA I, 23.1 +/- 11.2 to 115.0 +/- 17.9 nM for hCA II, and 0.7 +/- 0.3 to 4.4 +/- 1.0 nM for AChE. In comparison, the reference compound acetazolamide showed Ki values of 30.5 +/- 6.7 nM and 37.4 +/- 7.8 nM against hCA I and hCA II isoenzymes, respectively. Additionally, tacrine, a known AChE inhibitor, exhibited a Ki value of 5.1 +/- 2.7 nM. The dual inhibition of CA and AChE represents a valuable pharmacological approach with a wide range of therapeutic applications. The explanation and evaluation of the enzyme inhibition data obtained in line with the interactions of the synthesized compounds with hCA I, hCA II, and AChE enzymes were carried out by molecular docking studies. In particular, we focused on the three compounds (4e, 4f, and 4j for hCA I; 3g, 4f, and 4k for hCA II; and 4e, 4f, 4j, and 4l for AChE) with the highest potential activity with each enzyme. The physicochemical, ADME, drug-likeness, medicinal chemistry, and toxicity properties of the potential ligands were then predicted so that their drug candidate suitability for further studies is revealed.
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, Muhittin
The 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.
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, Muhittin
This 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.
Design, synthesis, characterization, crystal structure, in silico studies, and inhibitory properties of the PEPPSI type Pd(II)NHC complexes bearing chloro/fluorobenzyl group
(Academic Press Inc Elsevier Science, 2023) Gok, Yetkin; Taslimi, Parham; Sen, Betul; Bal, Selma; Aktas, Aydin; Aygun, Muhittin; Sadeghi, Morteza
This work contains synthesis, characterization, crystal structure, and biological activity of a new series of the PEPPSI type Pd(II)NHC complexes [(NHC)Pd(II)(3-Cl-py)]. NMR, FTIR, and elemental analysis techniques were used to characterize all (NHC)Pd(II)(3-Cl-py) complexes. Also, molecular and crystal structures of complex 1c were established by single-crystal X-ray diffraction. Regarding the X-ray studies, the palladium(II) atom has a slightly distorted square-planar coordination environment. Additionally, the enzyme inhibitory effect of new (NHC)Pd(II)(3-Cl-py) complexes (1a-1g) was studied. They exhibited highly potent inhibition effect on acetyl -cholinesterase (AChE), butyrylcholinesterase (BChE) and carbonic anhydrases (hCAs) (Ki values are in the range of 0.08 +/- 0.01 to 0.65 +/- 0.06 mu M, 10.43 +/- 0.98 to 22.48 +/- 2.01 mu M, 6.58 +/- 0.30 to 10.88 +/- 1.01 mu M and 6.34 +/- 0.37 to 9.02 +/- 0.72 mu M for AChE, BChE, hCA I, and hCA II, respectively). Based on the molecular docking, among the seven synthesized complexes, 1c, 1b, 1e, and 1a significantly inhibited AChE, BChE, hCA I, and hCA II enzymes, respectively. The findings highpoint that (NHC)Pd(II)(3-Cl-py) complexes can be considered as possible inhibitors via metabolic enzyme inhibition.
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]
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, Ilhami
meta-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.
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, Muhittin
A 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.
New morpholine or triphenylphosphine-liganded palladium(II) N-heterocyclic carbene complexes: Synthesis, characterization, crystal structure, and anticancer activity
(Elsevier Science Sa, 2026) Gok, Yetkin; Ozkan, Gul; Kurucay, Ali; Ates, Burhan; Aktas, Aydin; Demirci, Ozlem; Aygun, Muhittin
A series of morpholine(Morp.)-liganded palladium(II) complexes (1a-c) and triphenylphosphine(PPh3)-liganded palladium(II) complexes (2a-c) bearing 4-fluorobenzyl substituted N-heterocyclic carbene (NHC) were synthesized from NHC-Pd(II)-pyridine and Morp./PPh3 by ligand exchange method. The new complexes were fully characterized using 1H NMR, 13C NMR, 19F NMR, 31P NMR, FTIR spectroscopy and elemental analysis techniques. Furthermore, single crystal X-ray diffraction was used to elucidate the structures of complexes 1a and 2b. The anticancer activities of the new complexes against MCF-7 (Human Breast Cancer) cell line were investigated. With an IC50 value of 37.54 for complex 1a, it can be said that it is more cytotoxic to MCF-7 cells compared to other complexes, while the least cytotoxicity was observed in complex 1b.
New palladium complexes with N-heterocyclic carbene and morpholine ligands: Synthesis, characterization, crystal structure, molecular docking, and biological activities
(Wiley, 2024) Behcet, Ayten; Taslimi, Parham; Sen, Betul; Taskin-Tok, Tugba; Aktas, Aydin; Gok, Yetkin; Aygun, Muhittin
This work includes the synthesis of a new series of palladium-based complexes containing both morpholine and N-heterocyclic carbene (NHC) ligands. The new complexes were characterized using NMR (1H and 13C), FTIR spectroscopic, and elemental analysis techniques. The crystal structure of complex 1b was obtained by utilizing the single-crystal X-ray diffraction method. X-ray studies show that the coordination environment of palladium atom is completed by the carbene carbon atom of the NHC ligand, the nitrogen atom of the morpholine ring, and a pair of bromide ligand, resulting in the formation of slightly distorted square planar geometry. All complexes were determined for some metabolic enzyme activities. Results indicated that all the synthetic complexes exhibited powerful inhibitory actions against all aims as compared to the control molecules. Ki values of new morpholine-liganded complexes bearing 4-hydroxyphenylethyl group 1a-e for hCA I, hCA II, AChE, BChE, and alpha-glycosidase enzymes were obtained in the ranges 0.93-2.14, 1.01-2.03, 4.58-10.27, 7.02-13.75, and 73.86-102.65 mu M, respectively. Designing of reported complexes is impacted by molecular docking study, and interaction with the current enzymes also proclaimed that compounds 1e (-12.25 kcal/mol for AChE and -11.63 kcal/mol for BChE), 1c (-10.77 kcal/mol and -9.26 kcal/mol for alpha-Gly and hCA II, respectively), and 1a (-8.31 kcal/mol for hCA I) are showing binding affinity and interaction from the synthesized five novel complexes.
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, Parham
The 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.
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, Ilhami
This 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.
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, Ismail
In 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.
The palladium-based complexes bearing 1,3-dibenzylbenzimidazolium with morpholine, triphenylphosphine, and pyridine derivate ligands: synthesis, characterization, structure and enzyme inhibitions
(Cell Press, 2022) Aktas, Aydin; Yakali, Gul; Demir, Yeliz; Gulcin, Ilhami; Aygun, Muhittin; Gok, Yetkin
The palladium-based complexes bearing N-heterocyclic carbene (NHC) ligand have long attracted attention as active catalysts for many catalytic reactions. Recently, the biological activities of these complexes, which are stable to air and moisture, have also been wondered. With the aim, we report the synthesis of a series of (NHC) Pd(Br2)(L) complexes (NHC: 1,3-dibenzylbenzimidazolium, L: morpholine, triphenylphosphine, pyridine, 3-chloropyridine, and 2-aminopyridine). All complexes were characterized by NMR (1H and 13C), FTIR spectroscopic and elemental analysis techniques. In addition, the single crystal structures of the complex 3, 4, and 6 were determined through single crystal x-ray crystallographic method. Furthermore, the carbonic anhydrase I and II isoenzymes (hCAs) and acetylcholinesterase (AChE) inhibition effects of these palladium-based complexes bearing NHC ligand were investigated. They showed highly potent inhibition effect with Ki values are between 10.06 +/- 1.49-68.56 +/- 11.53 nM for hCA I isoenzyme, 7.74 +/- 0.66 to 49.39 +/- 6.50 nM for hCA II isoenzyme and 22.83 +/- 3.21 to 64.09 +/- 9.05 nM for AChE enzyme.
PEPPSI type Pd(II)NHC complexes bearing chloro-/fluorobenzyl group: Synthesis, characterization, crystal structures, ?-glycosidase and acetylcholinesterase inhibitory properties
(Pergamon-Elsevier Science Ltd, 2021) Bal, Selma; Demirci, Ozlem; Sen, Betul; Taslimi, Parham; Aktas, Aydin; Gok, Yetkin; Aygun, Muhittin
This work reported the synthesis of a new PEPPSI (Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation) type Pd(II)N-heterocyclic carbene (NHC) complexes bearing halo-benzyl (4-florobenzyl and 2-chloro-4-florobenzyl) group. These new complexes were synthesized from the florobenzyl / chlorofluorobenzyl substituted benzimidazolium salts, PdCl2 and pyridine. Characterizations of all the synthesized complexes were done using elemental analysis, H-1 NMR, C-13 NMR and FT-IR spectroscopy techniques. The molecular and crystal structures of the new PEPPSI type Pd(II)NHC complexes were determined by single-crystal X-ray diffraction method. X-ray studies show that molecular structures of three complexes comprise a palladium(II) atom with a slightly distorted square-planar coordination environment. These synthesized salts were found to be effective inhibitors for the alpha-glycosidase, and acetylcholinesterase (AChE) enzyme with K-i values in the range of 27.36 +/- 5.06-124.88 +/- 18.05 mu M for alpha-glycosidase, and 0.78 +/- 0.11-4.34 +/- 1.02 mu M for AChE, respectively. The significant group of drugs currently utilized for the therapy of Alzheimer's disease (AD) is acetylcholinesterase/cholinesterase inhibitor compounds. The first cholinesterase inhibitor licensed for symptomatic therapy of AD was tacrine. Inhibition acts of alpha-glycosidase enzyme by inhibitors tend to slow the breakdown and release of sugar molecules into the bloodstream and can be utilized as therapeutic factors in the therapy of obesity and diabetes. (C) 2021 Elsevier Ltd. All rights reserved.
PEPPSI-type N-heterocyclic carbene palladium(II) complexes as catalysts in the direct C5 arylation of furan and thiophene
(Elsevier Science Sa, 2025) Atakol, Arda; Yigit, Beyhan; Akdan, Hasan; Evren, Enes; Celepci, Duygu Barut; Yigit, Murat; Aygun, Muhittin
In this study, a series of amine-functionalized benzimidazolium salts and their PEPPSI-type N-heterocyclic carbene (NHC) palladium(II) complexes 3a-e were synthesized and characterized by FT-IR, 1H NMR and 13C NMR spectroscopy, elemental analysis, and mass spectrometry. The molecular and crystal structure of 3c and 3d was confirmed by the single-crystal X-ray diffraction (SC-XRD) method. Structural analysis reveals that the geometries of the PdII centers of the complexes adopt slightly distorted square planar environment. The new palladium complexes were tested as catalysts in the direct C5 arylation of 2-acetylfuran and 2-acetylthiophene with aryl bromides at 120 degrees C in N,N-dimethylacetamide. The arylation reactions proceeded selectively at the C5 position of the heteroaromatic compounds, and the corresponding coupling products were obtained in moderate to good yields by using 1 mol% of the palladium complex. Also, solid computational validation of the experimental results was achieved by geometric optimizations, frontier molecular orbital and molecular electrostatic potential studies, as well as natural bonding orbital analysis utilizing density functional theory.
Phthalimide-tethered imidazolium salts: Synthesis, characterization, enzyme inhibitory properties, and in silico studies
(Wiley-V C H Verlag Gmbh, 2022) Yigit, Murat; Demir, Yeliz; Celepci, Duygu Barut; Taskin-Tok, Tugba; Arinc, Ali; Yigit, Beyhan; Aygun, Muhittin
A series of new imidazolium salts were prepared in good yield by the reaction between 1-alkylimidazole and a variety of alkyl halides. The structures of the compounds were identified by FT-IR, H-1 NMR, and C-13 NMR spectroscopy, elemental analysis, and mass spectrometry. The crystal structure of 1b was determined by the single-crystal X-ray diffraction method. The phthalimide-tethered imidazolium salts exhibited inhibition abilities toward acetylcholinesterase (AChE) and human carbonic anhydrases (hCAs) I and II, with K-i values in the range of 24.63 +/- 3.45 to 305.51 +/- 35.98 nM for AChE, 33.56 +/- 3.71 to 218.01 +/- 25.21 nM for hCA I and 17.75 +/- 0.96 to 308.67 +/- 13.73 nM for hCA II. The results showed that the new imidazolium salts can play a key role in the treatment of Alzheimer's disease, epilepsy, glaucoma, and leukemia, which is related to their inhibition abilities of hCA I, hCA II, and AChE. Molecular docking and in silico absorption, distribution, metabolism, excretion and toxicity studies were used to look into how the imidazolium salts interacted with the specific protein targets. To better visualize and understand the binding positions and the influence of the imidazolium salts on hCA I, hCA II, and AChE conformations, each one was subjected to molecular docking simulations.
Platinum (II) N-heterocyclic carbene complexes: Synthesis, characterization and cytotoxic properties
(Wiley, 2019) Karaca, Emine Ozge; Ciftci, Osman; Ozdemir, Ilknur; Yakali, Gul; Aygun, Muhittin; Gurbuz, Nevin; Ozdemir, Ismail
Platinum (II) complexes bearing N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry, but there are very few reports of biological properties of this type of complexes. A series of [PtCl2(NHC)(PEt3)] complexes were synthesized. The structures of all compounds were characterized by H-1-NMR, C-13-NMR, IR and elemental analysis techniques, which supported the proposed structures. The single crystal structures of complexes 1a and 1e were determined. The title complexes show slightly distorted square-planar coordination around the platinum (II) metal center. The cytotoxic properties of the platinum (II)-NHC complexes have been assessed in various human cancer lines, including cisplatin-sensitive and resistant cells. IC50 values of these four complexes were determined by the MTS-based assay on three human cell lines-brain (SHSY5Y), colon (HTC116) and liver (HEP3B). These complexes have been highlighted cancer therapeutic agent with unique structures and functions.

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