Synthesis and alpha-Glucosidase and alpha-Amylase Inhibitory Activity Evaluation of Azido-and Aminocyclitols


Aydin G., Ally K., Aktas F., ŞAHİN E., BARAN A., BALCI M.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.31, pp.6903-6917, 2014 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2014
  • Doi Number: 10.1002/ejoc.201402762
  • Title of Journal : EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Page Numbers: pp.6903-6917
  • Keywords: Synthetic methods, Carbocycles, Cyclitols, Carbasugars, Amines, Biological activity, COST-EFFECTIVE CATALYST, SULFAMIC ACID, VALIOLAMINE, BISHOMOINOSITOLS, CONSTRUCTION, DERIVATIVES, EPOXIDATION, ACETOLYSIS, CHEMISTRY, ANALOGS

Abstract

For the synthesis of some azido-and aminocyclitols, (3aRS, 7aSR)-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 alpha-glucosidase and alpha-amylase were tested. The results indicated that some of these compounds seem to have good inhibitory activity against alpha-glucosidase, and low inhibitory activity against alpha-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.