Synthesis and Molecular Docking Study of Hydrazone Schiff Bases of α‐Naphthalene‐Containing Alkyl Phenyl Ether Fragment as Potent α‐Amylase and α‐Glucosidase Inhibitors
Tanzeela Ahmad Shah, Aftab Alam, Zainab Zainab, Mohammad Assad, Zahida Parveen, Huma Rafiq, Muhammad Ayaz, Syed Adnan Alı Shah, Abdul Latif, Mumtaz Ali, Manzoor Ahmad
Abstract
Abstract 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 1 H‐NMR and 13 C‐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 IC 50 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 IC 50 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.