Benzaldehyde derivatives with functional propargyl groups as α-glucosidase inhibitors

Abstract

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. α-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 α-glucosidase inhibition activity. Molecular docking studies were performed to investigate the binding interactions and interaction energies of the (1–6) compounds with the α-glucosidase inhibitor.