Novel <i>N</i>‐propylphthalimide‐ and 4‐vinylbenzyl‐substituted benzimidazole salts: Synthesis, characterization, and determination of their metal chelating effects and inhibition profiles against acetylcholinesterase and carbonic anhydrase enzymes

Sarı, Yakup; Aktaş, Aydın; Taslimi, Parham; Gök, Yetkın; Gülçın, İlhami

doi:10.1002/jbt.22009

Cited by 66 publications

(35 citation statements)

References 96 publications

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“…[55] In addition, hCA II is the most TA B L E 1 The enzyme inhibition results of novel amides of 1,1-bis-(carboxymethylthio)-1-arylethanes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11) extensively studied and characterized of the hCA isoforms. [58][59][60] [56] Acetylcholinesterase inhibitors (AChEIs) from natural plant, such as galantamine and TAC, are commonly used in pharmacotherapeutic therapies of alzheimer's disease (AD), whereas no butyrylcholinesterase inhibitors (BChEIs) have been recorded in natural plants.…”

Section: Discussionmentioning

confidence: 99%

Novel amides of 1,1‐bis‐(carboxymethylthio)‐1‐arylethanes: Synthesis, characterization, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase inhibitory properties

Taslimi

Osmanova

Çağlayan

et al. 2018

J Biochem & Molecular Tox

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The thiolation reaction was carried out in a benzene solution at 80°C and p-substituted ketones and mercaptoacetic acid in a molar ratio (1:4) of in the presence of a catalytic amount of toluene sulfonic acids. The enzyme inhibition activities of the novel amides of 1,1-bis-(carboxymethylthio)-1-arylethanes derivatives were investigated. These novel amides of 1,1-bis-(carboxymethylthio)-1-arylethanes derivatives showed good inhibitory action against acetylcholinesterase (AChE) butyrylcholinesterase (BChE), and human carbonic anhydrase I and II isoforms (hCA I and II). AChE inhibitors, interacting with the enzyme as their primary target, are applied as relevant drugs and toxins. Many clinically established drugs are carbonic anhydrase inhibitors, and it is highly anticipated that many more will eventually find their way into the market. The novel synthesized compounds inhibited AChE and BChE with K values in the range of 0.64-1.47 nM and 9.11-48.12 nM, respectively. On the other hand, hCA I and II were effectively inhibited by these compounds, with K values between 63.27-132.34 and of 29.63-127.31 nM, respectively.

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Section: Discussionmentioning

confidence: 99%

Novel amides of 1,1‐bis‐(carboxymethylthio)‐1‐arylethanes: Synthesis, characterization, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase inhibitory properties

Taslimi

Osmanova

Çağlayan

et al. 2018

J Biochem & Molecular Tox

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“…[1][2][3][4][5] These ligands have structural and unique electronic features such as strong σ-electron-donating character, weak π-accepting character, steric adjustability, and oxidation stability. [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. [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.…”

Section: Introductionmentioning

confidence: 99%

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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“…In the CA isoenzyme section, changes in absorbance were measured for 3 minutes at 348 nm. p ‐Nitrophenylacetate (PNA) was utilized as a substrate that was converted by both isoenzymes to the p ‐nitrophenolate according to the Verpoorte method, as described previously …”

Section: Methodsmentioning

confidence: 99%

Inhibition profiles of Voriconazole against acetylcholinesterase, α‐glycosidase, and human carbonic anhydrase I and II isoenzymes

Topal

2019

J Biochem & Molecular Tox

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In this work, the inhibitory activity of Voriconazole was measured against some metabolic enzymes, including human carbonic anhydrase (hCA) I and II isoenzymes, acetylcholinesterase (AChE), and α‐glycosidase; the results were compared with standard compounds including acetazolamide, tacrine, and acarbose. Half maximal inhibition concentration (IC50) values were obtained from the enzyme activity (%)‐[Voriconazole] graphs, whereas Ki values were calculated from the Lineweaver‐Burk graphs. According to the results, the IC50 value of Voriconazole was 40.77 nM for α‐glycosidase, while the mean inhibition constant (Ki) value was 17.47 ± 1.51 nM for α‐glycosidase. The results make an important contribution to drug design and have pharmacological applications. In addition, the Voriconazole compound demonstrated excellent inhibitory effects against AChE and hCA isoforms I and II. Voriconazole had Ki values of 29.13 ± 3.57 nM against hCA I, 15.92 ± 1.90 nM against hCA II, and 10.50 ± 2.46 nM against AChE.

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Novel N‐propylphthalimide‐ and 4‐vinylbenzyl‐substituted benzimidazole salts: Synthesis, characterization, and determination of their metal chelating effects and inhibition profiles against acetylcholinesterase and carbonic anhydrase enzymes

Abstract: The novel N-propylphthalimide-substituted and 4-vinylbenzyl-substituted N-heterocyclic carbene (NHC) precursors were synthesized by N-substituted benzimidazolium with aryl halides. The

Cited by 66 publications

References 96 publications

Novel amides of 1,1‐bis‐(carboxymethylthio)‐1‐arylethanes: Synthesis, characterization, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase inhibitory properties

Novel amides of 1,1‐bis‐(carboxymethylthio)‐1‐arylethanes: Synthesis, characterization, acetylcholinesterase, butyrylcholinesterase, and carbonic anhydrase inhibitory properties

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

Inhibition profiles of Voriconazole against acetylcholinesterase, α‐glycosidase, and human carbonic anhydrase I and II isoenzymes

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