Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-ß-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, characterized. The derivatives synthesized with good yields by base-catalyzed Claisen-Schmidt condensation in EtOH solution. Then these chalcones reacted TAGBr (2,3,4,6-tetra-O-acetyl-μ-D-glucopyranosylbromide) dry acetone under the anhydrous condition at 0-5 °C. Deacylated was carried out Zemplen's method NaOCH3 methanol results substituted chalcone-O-glycosides (mono- analogs). chemical structures of all compounds elucidated based on IR, NMR spectral data, mass spectrometry. Further, (7a-c, 8a-c, 12a-c, 16a-c, 17a-c) tested for their enzyme inhibition activity against μ-glycosidase, tyrosinase, AChE vitro silico analysis. Amongst them, 17a-c displayed moderate or less μ-glycosidase while other 7a-c 8a-c) not active. Remarkably interesting effects, IC$_{50}$ values below 30.59 ± 0.30 μM recorded 7c (IC$_{50}$=11.07 0.55 μM) tyrosinase.