28th Congress of SCTM

Synthesis and cholinesterase inhibitory evaluation of novel aryl derivatives of 2-(1H-imidazol-1-yl)acetic acid

Not scheduled

10m

Metropol Lake Resort

E-poster Organic chemistry, biochemistry and pharmaceutical chemistry

Speaker

Martina Šrajer Gajdošik (Josip Juraj Strossmayer University of Osijek - Department of Chemistry)

Description

Nitrogen-containing heterocyclic compounds based on the imidazole scaffold are frequently utilized in crop protection and medicinal chemistry due to their exceptional capacity to interact with diverse biological targets.1 In the field of agrochemicals, compounds disrupting the cholinergic nervous system through the inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) serve as vital tools for pest management and toxicological assessment. Therefore, exploring both enzymes is crucial for determining the efficacy, selectivity, and environmental safety of potential new screening candidates.2 In this study, a new series of arylamide derivatives of 2-(1H-imidazol-1-yl)acetic acid was synthesized using a modified Steglich amidation procedure under mild reaction conditions. The synthetic approach involved the use of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC × HCl) as the coupling reagent and 4-dimethylaminopyridine (DMAP) as the catalyst. Structural variation was achieved through the incorporation of differently substituted aromatic amines bearing electron-donating and electron-withdrawing groups, with the aim of exploring preliminary structure–activity relationships. The obtained compounds were characterized by melting point determination, ¹H and ¹³C NMR spectroscopy, and mass spectrometry. In addition, the synthesized derivatives were evaluated for their inhibitory activity against AChE and BuChE to assess their potential as cholinesterase inhibitors.

Keywords: 2-(1H-imidazol-1-yl)acetic acid, Steglich amidation, acetylcholinesterase, butyrylcholinesterase, cholinesterase inhibition

References:
1. Yadav, G; Jain, R. An insight into Synthetic, Structural and Medicinal perspective of imidazole analogs: A review European Journal of Medicinal Chemistry 2025, 290, 117524. https://doi.org/10.1016/j.ejmech.2025.117524

1. Karnaš, M; Rastija, V; Šubarić, D; Molnar, M. Green Synthesis and Acetylcholinesterase Inhibition of Coumarin-1,2,4-Triazole Hybrids. Curr. Org. Chem. 2023, 27, 883–892. https://doi.org/10.2174/1385272827666230817145725