Synthesis and α-Glucosidase and α-Amylase Inhibitory Activity Evaluation of Azido- and Aminocyclitols.

For the synthesis of some azido- and aminocyclitols, (3a RS,7a SR)-1,3,3a,7a-tetrahydroisobenzofuran was used as the starting material. For further functionalization of the diene unit, the diene was subjected to epoxidation reactions to give mono- and bisepoxides depending on the amount of m-chloroperbenzoic acid used. The ring-opening of the epoxide functionality with NaN3 resulted in the formation of mono- and bisazido cyclitols. The tetrahydrofuran ring was opened in an acid-catalysed reaction with sulfamic acid. The reduction of azide groups to give amines provided various amino- and bisaminocyclitol derivatives. The inhibitory effects of 20 compounds against α-glucosidase and α-amylase were tested. The results indicated that some of these compounds seem to have good inhibitory activity against α-glucosidase, and low inhibitory activity against α-amylase. Furthermore, it was demonstrated that the number and position of azides, amines, and hydroxy groups appeared to play an important role in determining the inhibitory potency of these compounds. [ABSTRACT FROM AUTHOR]