Novel NHC Precursors: Synthesis, Characterization, and Carbonic Anhydrase and Acetylcholinesterase Inhibitory Properties

Abstract

Three series of imidazolidinium ligands (NHC precursors) substituted with 4-vinylbenzyl, 2-methyl-1,4-benzodioxane, and N-propylphthalimide were synthesized. N-Heterocyclic carbene (NHC) precursors were prepared from N-alkylimidazoline and alkyl halides. The novel NHC precursors were characterized by H NMR, C NMR, FTIR spectroscopy, and elemental analysis techniques. The enzymes inhibition activities of the NHC precursors were investigated against the cytosolic human carbonic anhydrase I and II isoenzymes (hCA I and II) and the acetylcholinesterase (AChE) enzyme. The inhibition parameters (IC and K values) were calculated by spectrophotometric method. The inhibition constants (K ) were found to be in the range of 166.65-635.38 nM for hCA I, 78.79-246.17 nM for hCA II, and 23.42-62.04 nM for AChE. Also, the inhibitory effects of the novel synthesized NHCs were compared to acetazolamide as a clinical CA isoenzymes inhibitor and tacrine as a clinical cholinergic enzymes inhibitor.

The impact of some natural phenolic compounds on carbonic anhydrase, acetylcholinesterase, butyrylcholinesterase, and α‐glycosidase enzymes: An antidiabetic, anticholinergic, and antiepileptic study

“…In this part, 5,5′‐dithio‐bis(2‐nitro‐benzoic)acid (DTNB) was used for the estimation of the BChE/AChE activities. Briefly, 100 μL of buffer solution (pH 8.0, Tris/HCl, 1.0 M) and diverse concentration of sample solutions (50–200 μL) dissolved in deionized water were added to 50 μL of BChE/AChE solutions (5.32 × 10 −3 EU) . Then the mixture was incubated for 10 min at 20°C.…”

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

“…[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.…”

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

“…[25][26][27][28][29] In this study, we have performed the synthesis of well-defined novel amide of 1,1-bis-(carboxymethylthio)-1-arylethanes derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11). [25][26][27][28][29] In this study, we have performed the synthesis of well-defined novel amide of 1,1-bis-(carboxymethylthio)-1-arylethanes derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11).…”