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<p>In this study, 4,6-dimethoxy-2-phenylbenzofurans and 4,6-dimethyl-2-phenylbenzofurans were synthesized through the reactions of 3,5-dimethoxyphenol and 3,5-dimethylphenol with <i>α</i>-bromoacetophenone derivatives, respectively. The resulting benzofuran derivatives were then subjected to the Vilsmeier–Haack reaction to generate the corresponding benzofuran carbaldehydes. The aldehyde formation occurred at the C7 position in dimethoxybenzofuran compounds, while in dimethylbenzofuran compounds it took place at the C3 position. In the final step of the synthesis, the benzofuran carbaldehydes were reacted with commercially available diamines to produce the target benzofuranyl-benzimidazoles. The inhibitory effects of the synthesized compounds, investigated for their anti-diabetic potential, were evaluated against α-amylase and α-glucosidase enzymes. The compounds exhibited superior inhibitory potency compared to the analogs. Structure–activity relationship analysis revealed that substitution at the C3 position of the benzofuran ring and the presence of electron-donating or electron-withdrawing groups significantly influenced enzyme inhibition. Molecular docking studies indicated that hydrogen bonding and hydrophobic interactions contribute to enzyme binding. These findings suggest that methyl-substituted benzofuran–benzimidazole scaffolds offer promising leads for the development of new α-amylase and α-glucosidase inhibitors with optimized pharmacokinetic profiles.</p> Graphical abstract <p></p>

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Synthesis, in vitro, and in silico studies of novel benzofuran–benzimidazole hybrids as potential α-amylase and α-glucosidase inhibitor

  • 期刊论文

  • 发表日期：

    2026年6月28日

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  • İcal Ocak,
  • Tuğçe Nur Uslu Uçar,
  • Samet İzgi,
  • Murat Bingul,
  • Hasan Sahin,
  • Alev Arslantürk Bingül,
  • Hakan Kandemir,
  • Ibrahim F. Sengul

摘要

In this study, 4,6-dimethoxy-2-phenylbenzofurans and 4,6-dimethyl-2-phenylbenzofurans were synthesized through the reactions of 3,5-dimethoxyphenol and 3,5-dimethylphenol with α-bromoacetophenone derivatives, respectively. The resulting benzofuran derivatives were then subjected to the Vilsmeier–Haack reaction to generate the corresponding benzofuran carbaldehydes. The aldehyde formation occurred at the C7 position in dimethoxybenzofuran compounds, while in dimethylbenzofuran compounds it took place at the C3 position. In the final step of the synthesis, the benzofuran carbaldehydes were reacted with commercially available diamines to produce the target benzofuranyl-benzimidazoles. The inhibitory effects of the synthesized compounds, investigated for their anti-diabetic potential, were evaluated against α-amylase and α-glucosidase enzymes. The compounds exhibited superior inhibitory potency compared to the analogs. Structure–activity relationship analysis revealed that substitution at the C3 position of the benzofuran ring and the presence of electron-donating or electron-withdrawing groups significantly influenced enzyme inhibition. Molecular docking studies indicated that hydrogen bonding and hydrophobic interactions contribute to enzyme binding. These findings suggest that methyl-substituted benzofuran–benzimidazole scaffolds offer promising leads for the development of new α-amylase and α-glucosidase inhibitors with optimized pharmacokinetic profiles.

Graphical abstract