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

What is it about?

This study contains synthesis of three series of imidazolidinium ligands (NHC precursors) that 4-vinylbenzyl, 2-methyl-1,4-benzodioxane and N-propylphthalimide substituted. The NHC precursors have been prepared from N-alkylimidazoline and alkyl halides. The novel NHC precursors have been characterized by using 1H NMR, 13C NMR, FTIR spectroscopy and elemental analysis techniques. 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 acetylcholinesterase (AChE) and their inhibition parameters (IC50 and Ki) were calculated by spectrophotometric method. The inhibition constants (Ki) were found in the range of 166.65-635.38 pM for hCA I, 78.79-246.17 pM for hCA II, and 23.42-62.04 pM for AChE. Also, the inhibitory effects of the novel synthesized NHCs were compared to acetazolamide (AZA) as a clinical CA isoenzymes inhibitor and tacrine (TAC) as a clinical AChE enzyme inhibitor.

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Why is it important?

As discussed above, NHC precursors can be good candidate drugs for the treatment of some diseases like glaucoma, epilepsy, mountain sickness, gastric and duodenal ulcers, neurological disorders, or osteoporosis as carbonic anhydrase inhibitors and for the treatment of AD and PD as ACHE inhibitors.

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