Synthesis, characterization, and biocomputational assessment of the novel 3-hydroxy-4-(phenyl(pyridin-2-ylamino) methyl)-2-naphthoic acid derivatives as potential dual inhibitors of α-glucosidase and α-amylase enzymes

One-pot synthesis of 3-hydroxy-4-(phenyl(pyridin-2-ylamino) methyl)-2-naphthoic acid derivatives were synthesized by using 3-hydroxy-2-naphthoic acid, aromatic aldehyde, and pyridin-2-amine by refluxing at 140 degrees C and these derivatives were screened for biological activity as well as computational studies, in that majority of the compounds showed positive results. All synthesized molecules were characterized by analytical technics like H-1 NMR and FT-IR. As compared to the control, acarbose (IC50: 0.30 +/- 0.08 mg/mL for alpha-amylase and 0.10 +/- 0.06 for alpha-glucosidase), the compound DMBA (7,12-Dimethylbenz[a]anthracene) nearly inhibited alpha-glucosidase (IC50: 0.35 +/- 0.34 mg/mL) and alpha-amylase (0.11 +/- 0.17 mg/ml) during in vitro inhibition. The DMBA molecule exhibits a good binding affinity (-9.8 kcal/mol for alpha-glucosidase and -6.6 kcal/mol for alpha-amylase) compared to that of acarbose (-8.6 kcal/mol and -7.8 kcal/mol, respectively), according to molecular docking studies. The stability of the DMBA molecule was demonstrated by molecular dynamics simulations and estimations of the binding free energy over the course of the simulation session (100 ns). In this context, we report DMBA as a potential dual inhibitor of both alpha-glucosidase and alpha-amylase enzymes.