Synthesis and α-Glucosidase Inhibitory Activity of Coumarin-3-Carboxylates
α-Glucosidase Inhibitory Activity of Coumarin-3-Carboxylates
Keywords:
α-Glucosidase inhibitory activity, Coumarin-3-carboxylates, Coumarin-3-carboxylic acid, EsterificationAbstract
α-Glucosidase inhibitors represent an important role in the treatment of diabetes. Although many synthetic inhibitors have been reported, novel and more efficient compounds are still necessary to exhibit this activity. Coumarins are aromatic substances composed of fused benzene and α-pyrone rings and display a wide variety of biological activities, especially α-glucosidase inhibitory activity. This research aimed to study the structural modification of coumarin-3-carboxylic acid into coumarin-3-carboxylates to enhance their α-glucosidase inhibitory activity. Eight coumarin-3-carboxylates were successfully synthesized by esterification using coumarin-3-carboxylic acid and alcohols as starting materials. The desired products were obtained in 17−65% yields. All synthesized compounds were examined for their α-glucosidase inhibitory activity. The results found that (-)-menthyl coumarin-3-carboxylate was the most potent inhibitor against α-glucosidase with an IC50 of 7.16±1.87 μM, followed by 2-phenylethyl coumarin-3-carboxylate with an IC50 of 11.70±2.66 μM. Both compounds were first reported to exhibit 30-49 folds activity more efficiently than acarbose and could be further developed into a new potential antidiabetic drug.
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