Synthesis of 1,2,3-triazole glycoconjugates as inhibitors of α-glucosidases

Ten new 1,2,3-triazole glycoconjugates were synthesized from d-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme α-glucosidase. Most of the compounds had low activity or were inactive when compared with acarbose. However, the derivative 1,2-O-isopropylidene-3-phenyl-5-(4-phenyl-1H-1,2,3-triazole-1-yl)-α-d-ribofuranose (19i) possessed activity comparable with the standard drug. The influence of the phenyl group on carbon 3 of the carbohydrate framework is discussed.

Graphical abstractTen new 1,2,3-triazole glycoconjugates were synthesized from d-glucose and evaluated in in vitro assays for their ability to inhibit the enzyme α-glucosidase.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► We synthesize 10 new 1,2,3-triazole glycoconjugates (19a–j) from d-glucose. ► They were evaluated for their ability to inhibit the enzyme α-glucosidase. ► The IC50 revealed that 19i (119.5 ± 0.1 μM) had a similar potency to acarbose.