Synthesis, antioxidant, antidiabetic, molecular docking and ADMET evaluation of indenoquinoxalines-carbazides compounds

Abstract

In this study, we report the synthesis of indenoquinoxalines heterocycles linked to carbazides moiety, including thiosemicarbazides, semicarbazides, and aminoguanidines. The structure of the compounds was confirmed using various spectroscopic techniques, such as ¹H NMR, ¹³C NMR, FT-IR spectroscopy, and mass spectrometry. The synthesized compounds were then evaluated for their antioxidant activities using the DPPH and CUPRIC methods. The results demonstrated that our compounds exhibited satisfactory antioxidant potential, with compound 5c surpassing ascorbic acid in reducing power as evaluated by the CUPRAC with A_0.50 = 0.070 ± 0.018 mg/mL. Furthermore, the in vitro antidiabetic activity measured by determining the glucose uptake using the yeast cells has shown promising results with absorption percentages ranging from 12 to 84 % using different concentrations of glucose, suggesting an interesting potential for blood glucose control. Molecular docking study demonstrated the potential of these molecules as potential α-glucosidase inhibitors. By showing a superior stability of all the enzyme-ligand complexes formed compared to the reference molecule, acarbose. Additionally, drug-likeness parameters, along with ADMET properties, were evaluated, suggesting a favorable pharmacokinetic profile for our compounds.