TY  - JOUR
TI  - Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies
AB  - 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.
AU  - Barut, Burak
AU  - Sahin, Huseyin
AU  - Tatar Yılmaz, Gizem
AU  - ÇELİK, Gonca
AU  - YAYLI, Nurettin
DO  - 10.55730/1300-0527.3527
PY  - 2023
JO  - Turkish Journal of Chemistry
VL  - 47
IS  - 1
SN  - 1300-0527
SP  - 171
EP  - 184
DB  - TRDizin
UR  - http://search/yayin/detay/1158713
ER  -