Benzaldehyde derivatives with functional propargyl groups as ?-glucosidase inhibitors

The benzaldehyde derivatives (1-6) containing one and/or two propargyl arm(s) attached to the phenolic hydroxyl oxygen atom on the ortho-, meta- or para-positions of the aromatic ring were synthesized and characterized by spectral and microanalytical methods. The molecular structures were of 1, 4-6 determined by the single crystal X-ray crystallography. The benzaldehyde derivatives containing free phenolic groups involved intra- and inter-molecular hydrogen bonding interactions. The electrochemical properties of the compounds were investigated at the different scan rates and it was found that the compounds show different electrochemical behaviors. alpha-Glucosidase inhibitor properties of the carbonyl compounds were investigated and it has been determined that some of them show high activity. Compounds with a free phenolic group (-OH) exhibit better inhibition activity than compounds with no free phenolic group. It was also found that the position of propargyl group played an important role in the alpha-glucosidase inhibition activity. Molecular docking studies were performed to investigate the binding interactions and interaction energies of the (1-6) compounds with the alpha-glucosidase inhibitor. (C) 2020 Elsevier B.V. All rights reserved.