Synthesis, antidiabetic activity and molecular docking study of rhodanine-substitued spirooxindole pyrrolidine derivatives as novel α-amylase inhibitors

Nineteen novel rhodanine-fused spiro[pyrrolidine-2,3'-oxindoles] were synthesized with α-amylase inhibitory activity showing IC values between 1.49 ± 0.10 and 3.06 ± 0.17 µM.

• Compounds displayed good α-amylase inhibition compared to the control drug acarbose, which has an IC value of 1.56 µM.
• The synthesis involved a one-pot three-component cycloaddition process that created structurally diverse compounds with four contiguous stereocenters.
• The stereochemistry of the synthesized compounds was confirmed through NMR and X-ray diffraction analysis.
• In vivo testing on alloxan-induced diabetic rats indicated that certain spiropyrrolidine derivatives reduced blood glucose levels.
• Molecular docking studies were conducted to model the binding interactions of the most active derivatives.

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