| Summary: | In this study, new Schiff base derivatives of α-naphthalene acetic acid containing alkyl phenyl ether fragment have been effectively synthesized through multistep reaction process, characterized by 1H-NMR and 13C-NMR spectroscopy. These derivatives have been tested for their in vitro α-amylase and α-glucosidase inhibitory activities. In the series, 8 compounds (2j, 2f, 2e, 2m, 2a, 2b, 2l, and 2c) exhibited promising α-amylase inhibition with IC50 values from 5.38 ± 0.36 to 14.59 ± 0.64 µg/mL. Similarly, in the case of α-glucosidase inhibitory activity, 10 derivatives (2e, 2f, 2j, 2m, 2b, 2c, 2i, 2d, 2a, and 2l) exhibited excellent activity having IC50 values from 6.96 ± 0.39 to 16.27 ± 0.31 µg/mL, wheras the remaining derivatives exhibited good-to-least antidiabetic potential. The ADME properties were calculated for all Schiff base derivatives using Swiss-ADME web tool. Furthermore, the docking studies identified the binding modes of the compounds. © 2024 Wiley-VCH GmbH.
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