Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies

In this study, some novel mono- and di- O -β-D-glycopyranosyl chalcone analogs were designed, synthesized, and characterized. The chalcone derivatives were synthesized with good yields by base-catalyzed Claisen-Schmidt condensation in EtOH solution. Then these chalcones were reacted with TAGBr (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide) in dry acetone under the anhydrous condition at 0–5 °C. Deacylated was carried out by the Zemplen’s method with NaOCH 3 in dry methanol results in substituted chalcone- O -glycosides (mono- and di- O -β-D-glycopyranosyl chalcone analogs). The chemical structures of all synthesized compounds were elucidated based on IR, NMR spectral data, and mass spectrometry. Further, the compounds ( 7a–c, 8a–c, 12a–c, 16a–c, and 17a–c ) were tested for their enzyme inhibition activity against α-glycosidase, tyrosinase, and AChE with in vitro and in silico analysis. Amongst them, compounds 12a–c, 16a–c, and 17a–c displayed moderate or less enzyme inhibition activity against α-glycosidase while other compounds 7a–c and 8a–c ) were not active. Remarkably interesting enzyme inhibition effects, with IC 50 values below 30.59 ± 0.30 μM were recorded with 7c (IC 50 =11.07 ± 0.55 μM) against tyrosinase.