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<p>In this work, a new series of tetra-substituted imidazole derivatives (5a–5j) was synthesized via a condensation reaction of benzil, various aromatic aldehydes, primary aromatic amine, and ammonium acetate, using eco-friendly CrFe<sub>2</sub>O<sub>4</sub> nanoparticles as a catalyst. Both conventional and ultrasound-assisted methods provided cost-effectiveness, simplicity, and high yields (79–96%). Comprehensive characterization of the catalyst was performed using FT-IR to examine chemical bonds, XRD to determine crystal structure, SEM for surface morphology, and EDX for elemental composition. The synthesized compounds (5a–j) were characterized by FT-IR, <sup>1</sup>H and <sup>13</sup>C NMR, and C.H.N analysis. This study aimed to design and synthesize new tetrasubstituted imidazole derivatives with enhanced antidiabetic activity. The approach utilized their structural flexibility to inhibit key carbohydrate-digesting enzymes, α-amylase and α-glucosidase, effectively. This research offers potential compounds for future drug development. All derivatives were evaluated for their in vitro and in silico inhibitory effects against α-amylase and α-glucosidase using acarbose as a reference drug. Among them, compounds 5i, 5c, 5f, 5&#xa0;h, and 5j exhibited the highest activity against α-amylase with an IC₅₀ of 43 ± 0.09, 53 ± 0.04, 54 ± 0.01, 75 ± 0.342 and 28 ± 1.74 µM, respectively, which is significantly lower than that of acarbose 148 ± 0. 06 µM. In contrast, against α-glucosidase, the compounds showed moderate inhibition with IC₅₀ values ​​ranging from 187 ± 1.54 to 398 ± 7.78 µM, compared to acarbose (114 ± 3.68 µM). These findings indicate that the synthesized derivatives, especially compound 5j, exhibit promising α-amylase inhibition and moderate α-glucosidase inhibition. Overall, this work presents a sustainable synthetic protocol and introduces new imidazole derivatives with promising antidiabetic potential, making them valuable candidates for future drug discovery and development.</p>

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Design, Synthesis, Bioactivity Evaluation, and Molecular Docking of New 1,2,4,5-Tetrarylimidazole Derivatives as Antidiabetic Agents

  • 期刊论文

  • 发表日期：

    2025年12月20日

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  • Sawsan K. Abbas,
  • Mohammed Thamer Jaafar,
  • Hayder Raheem Ali,
  • Luma M. Ahmed

摘要

In this work, a new series of tetra-substituted imidazole derivatives (5a–5j) was synthesized via a condensation reaction of benzil, various aromatic aldehydes, primary aromatic amine, and ammonium acetate, using eco-friendly CrFe2O4 nanoparticles as a catalyst. Both conventional and ultrasound-assisted methods provided cost-effectiveness, simplicity, and high yields (79–96%). Comprehensive characterization of the catalyst was performed using FT-IR to examine chemical bonds, XRD to determine crystal structure, SEM for surface morphology, and EDX for elemental composition. The synthesized compounds (5a–j) were characterized by FT-IR, 1H and 13C NMR, and C.H.N analysis. This study aimed to design and synthesize new tetrasubstituted imidazole derivatives with enhanced antidiabetic activity. The approach utilized their structural flexibility to inhibit key carbohydrate-digesting enzymes, α-amylase and α-glucosidase, effectively. This research offers potential compounds for future drug development. All derivatives were evaluated for their in vitro and in silico inhibitory effects against α-amylase and α-glucosidase using acarbose as a reference drug. Among them, compounds 5i, 5c, 5f, 5 h, and 5j exhibited the highest activity against α-amylase with an IC₅₀ of 43 ± 0.09, 53 ± 0.04, 54 ± 0.01, 75 ± 0.342 and 28 ± 1.74 µM, respectively, which is significantly lower than that of acarbose 148 ± 0. 06 µM. In contrast, against α-glucosidase, the compounds showed moderate inhibition with IC₅₀ values ​​ranging from 187 ± 1.54 to 398 ± 7.78 µM, compared to acarbose (114 ± 3.68 µM). These findings indicate that the synthesized derivatives, especially compound 5j, exhibit promising α-amylase inhibition and moderate α-glucosidase inhibition. Overall, this work presents a sustainable synthetic protocol and introduces new imidazole derivatives with promising antidiabetic potential, making them valuable candidates for future drug discovery and development.