Synthesis, characterization, crystal structure, and antimicrobial studies of 2-morpholinoethyl-substituted benzimidazolium salts and their silver(I)-N-heterocyclic carbene complexes

Yildirim, İşıl; Aktaş, Aydın; Celepci, Duygu Barut; Kırbağ, Sevda; Kutlu, Türkan; Gök, Yetkın; Aygün, Muhıttın

doi:10.1007/s11164-017-2995-3

Cited by 29 publications

(18 citation statements)

References 26 publications

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“…In this study, two new 2-hydroxyethyl substituted NHC precursors 1 and 2 were synthesized, characterized using FT-IR, 1 H, 13 C NMR, and UV-Vis spectroscopy. Crystal and molecular structures of the compounds were determined using the single-crystal X-ray diffraction method.…”

Section: Discussionmentioning

confidence: 99%

“…; 4.56 (t, 2H, J: 6 MHz, -NCH 2 CH 2 OH); 5.18 (s, 1H, -NCH 2 CH 2 OH); 7.69-8.32 (m, 4H, -N(C 6 H 4 )N-Ar-H); and 9.69 (s, 1H, 2-CH). 13…”

Section: Synthesis Of 1-(2-hydroxyethyl)-3-methylbenzimidazolium Chmentioning

confidence: 99%

“…[6][7][8] Recently, studies on strong enzyme inhibition effects of NHC precursors have been published. [12][13][14][15][16][17] The studies on the structural and electronic properties of NHC precursors have just been published recently. [12][13][14][15][16][17] The studies on the structural and electronic properties of NHC precursors have just been published recently.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11] NHC-metal complexes that have been synthesized from NHC ligands and transition metals exhibited very good biological activity as well as a strong catalytic effect. [12][13][14][15][16][17] The studies on the structural and electronic properties of NHC precursors have just been published recently. [18,19] In this study, we have investigated the structural and electronic properties of two new benzimidazolium salts (NHC precursors) using the single-crystal X-ray diffraction method and spectroscopic techniques.…”

Section: Introductionmentioning

confidence: 99%

“…4H, -N(C 6 H 4 )N-Ar-H); and 9.02 (s, 1H, 2-CH) 13. C NMR (100 MHz, DMSO-d 6 ); δ 16.9-17.2-17.5 (-NCH 2 (C 6 (CH 3 ) 5 ); 46.8 (-NCH 2 CH 2 OH); 49.8 (-NCH 2 (C 6 (CH 3 ) 5 ); 59.1 (-NCH 2 CH 2 OH); 114.3-114.6-126.0-127.0-127.1-131.9-132.2-133.4-134.4-136.7 (Ar-C); 141.8 (2-CH).…”

mentioning

confidence: 99%

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Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

Aktaş

Celepci

Gök

2019

J Chinese Chemical Soc

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This study discusses the synthesis of two new 2‐hydroxyethyl substituted N‐heterocyclic carbene (NHC) precursors. The NHC precursors were prepared from 1‐(alkyl/aryl)benzimidazole and alkyl halides. They were characterized using 1H NMR, 13C NMR, FT‐IR, UV–Vis spectroscopy, and elemental analysis techniques. Molecular and crystal structures of 1 and 2 were determined using the single‐crystal X‐ray diffraction method. Crystal structure of the compounds features NHC precursors and chloride anions. Additionally in 2, the asymmetric unit has a water molecule, which forms a tetrameric chloride‐hydrate assembly with the chloride anion. The chloride anions play an important role in the stabilization of crystal structures to form a two‐dimensional supramolecular architecture. The 3D Hirshfeld surface and the associated 2D fingerprint plots were also drawn to gain insights into the behavior of the interactions in the compounds.

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Section: Discussionmentioning

confidence: 99%

“…; 4.56 (t, 2H, J: 6 MHz, -NCH 2 CH 2 OH); 5.18 (s, 1H, -NCH 2 CH 2 OH); 7.69-8.32 (m, 4H, -N(C 6 H 4 )N-Ar-H); and 9.69 (s, 1H, 2-CH). 13…”

Section: Synthesis Of 1-(2-hydroxyethyl)-3-methylbenzimidazolium Chmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

Aktaş

Celepci

Gök

2019

J Chinese Chemical Soc

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Silver N‐heterocyclic carbene complexes bearing fluorinated benzyl group: Synthesis, characterization, crystal structure, computational studies, and inhibitory properties against some metabolic enzymes

Bal

Demirci

Şen

et al. 2021

Applied Organom Chemis

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A series of the silver N‐heterocyclic carbene (NHC) complexes have been synthesized from the reactions between benzimidazolium salts bearing fluorinated benzyl group and Ag2O via the deprotonation method. All Ag(I)NHC complexes were characterized by known spectroscopic techniques (1H nuclear magnetic resonance [NMR], 13C NMR, and Fourier transform infrared [FT‐IR]) and elemental analysis. The molecular structures of the two complexes were unambiguously elucidated through single‐crystal X‐ray diffraction analysis. Namely, X‐ray studies show that the coordination geometry around the Ag(I) atom in the case of complex 2c is revealed to be almost linear with C–Ag–Cl angle, whereas in complex 2e, it appears as a nonlinear structure. The inhibitory profiles of these new complexes are investigated on some metabolic enzymes. Representatively, the most potent complex against human carbonic anhydrase isoenzymes I and II (hCAs I and II), 2d, was 1.8 times more potent than standard inhibitor acetazolamide against hCAs I and II. On the other hand, complexes 2c and 2b as most potent compounds against both cholinesterase enzymes was around 5 and 1.6 times more potent than tacrine against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively. The most active α‐glucosidase inhibitor 2d had similar activity to acarbose as a standard inhibitor. Furthermore, it confirms its in vitro studies as a result of molecular docking studies for each enzyme with (i) binding energy and inhibition constant values and (ii) the definition of the best conformation and nonbonding interactions of the related complexes (2b, 2c, and 2d) against the different target proteins.

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meta‐Cyanobenzyl substituted benzimidazolium salts: Synthesis, characterization, crystal structure and carbonic anhydrase, α‐glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties

Türker

Celepci

Aktaş

et al. 2018

Archiv der Pharmazie

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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 NMR, C 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 α-glycosidase (AG), the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), butyrylcholinesterase (BChE), and acetylcholinesterase (AChE) with K values in the range of 1.01-2.12 nM for AG, 189.56-402.44 nM for hCA I, 112.50-277.37 nM for hCA II, 95.45-352.58 nM for AChE, and 132.91-571.18 nM 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.

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Synthesis, characterization, crystal structure, and antimicrobial studies of 2-morpholinoethyl-substituted benzimidazolium salts and their silver(I)-N-heterocyclic carbene complexes

Cited by 29 publications

References 26 publications

Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

Synthesis, crystal structures, spectral FT‐IR, NMR and UV–Vis investigations and Hirshfeld surface analysis of two new 2‐hydroxyethyl‐substituted N‐heterocyclic carbene precursors

Silver N‐heterocyclic carbene complexes bearing fluorinated benzyl group: Synthesis, characterization, crystal structure, computational studies, and inhibitory properties against some metabolic enzymes

meta‐Cyanobenzyl substituted benzimidazolium salts: Synthesis, characterization, crystal structure and carbonic anhydrase, α‐glycosidase, butyrylcholinesterase, and acetylcholinesterase inhibitory properties

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