Preparation of polysubstituted imidazoles using AC-SO3H/[Urea]7[ZnCl2]2 as an efficient catalyst system: a novel method, and α-glucosidase inhibitor activity

Abstract

Deep eutectic solvents (DESs) act as both an organic solvent and a useful catalyst for organic synthesis reactions, especially the synthesis of heterocyclic compounds containing the element nitrogen. DESs exhibit many important properties namely large liquid fields, biodegradability, outstanding thermal stability, and moderate vapor pressure. Amorphous carbon-bearing sulfonic acid groups (AC-SO₃H) are one of the new-generation solid acids showing strong acid activity. Based on the simultaneous presence of acidic functional groups such as carboxylic acid, phenolic, and sulfonic acid groups, they exhibit many important activities namely strong Brønsted acid, high surface area, high stability, reusability, and recyclability. In this study, AC-SO₃H was made from rice husk via the carbonization and sulfonation processes, and the surface properties and structure were examined using contemporary methods such as FT-IR, P-XRD, TGA, SEM, and EDS. And, [Urea]₇[ZnCl₂]₂ was synthesized from urea and ZnCl₂ with a mole ratio of 7 : 2; the structure is defined using FT-IR and TGA. By combining AC-SO₃H and [Urea]₇[ZnCl₂]₂ we aim to form an effective catalyst/solvent system for the preparation of polysubstituted imidazole derivatives through the multi-component cyclization reaction from nitrobenzenes, benzil, aldehydes, and ammonium acetate. The major products are obtained with high isolation yields above 60%. To assess the catalyst system's activity, the recovery and reusability of the AC-SO₃H/[Urea]₇[ZnCl₂]₂ system were examined with hardly any performance modification. In an effort to create potential enzyme α-glucosidase inhibitors, several novel polysubstituted imidazoles were created. Five of these compounds showed good enzyme α-glucosidase inhibitor activity. The most effective substances were IMI-13, IMI-15, and IMI-20, with IC₅₀ values that were greater than the acarbose at 16.5, 15.8, and 11.6 μM, respectively – the acarbose (IC₅₀, 214.5 μM) as the positive control.