Synthesis of a salacinol analogue and its α-glucosidase inhibitory activity

AimTo investigate more efficient synthetic method of the nitrogen analogue 4 of salacinol (1) for searching new antidiabetic agents. MethodsThe synthesis of the key intermediate 2,4-o-isopropylidene-l-erythritol 1,3-cyclic sulfate (2a) was accomplished by modification of reports from d-glucose via seven steps in much more less expensive. Using this method, an efficient synthesis of 4 was carried out. The glycosidase inhibitory activity of 4 was tested for the intestinal α-glucosidase In vitro and compared with that of salacinol. ResultsA nitrogen analogue 4 of salacinol (1) was synthesized by the coupling reaction between the cyclic sulfate 2a and an azasugar 3b. ConclusionSubstitution of the sulfur atom in 1 with a nitrogen reduced the activity considerably.