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

• Published in: CHEMISTRYSELECT
• Main Authors: Shah, Tanzeela Ahmad; Alam, Aftab; Zainab; Assad, Mohammad; Parveen, Zahida; Rafiq, Huma; Ayaz, Muhammad; Shah, Syed Adnan Ali; Latif, Abdul; Ali, Mumtaz; Ahmad, Manzoor
• Format: Article
• Language: English
• Published: WILEY-V C H VERLAG GMBH 2024
• Subjects: Chemistry
• Online Access: https://www-webofscience-com.uitm.idm.oclc.org/wos/woscc/full-recordWOS:001368734100001

In this study, new Schiff base derivatives of alpha-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 alpha-amylase and alpha-glucosidase inhibitory activities. In the series, 8 compounds (2j, 2f, 2e, 2m, 2a, 2b, 2l, and 2c) exhibited promising alpha-amylase inhibition with IC50 values from 5.38 +/- 0.36 to 14.59 +/- 0.64 mu g/mL. Similarly, in the case of alpha-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 mu g/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.