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

Date

2014-11-01

Author

Aydin, Gokay
Ally, Khamis
Aktas, Fatih
ŞAHİN, Ertan
BARAN, ARİF
Balcı, Metin

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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.

Subject Keywords

Physical and Theoretical Chemistry, Organic Chemistry

URI

https://hdl.handle.net/11511/56968

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1002/ejoc.201402762

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

G. Aydin, K. Ally, F. Aktas, E. ŞAHİN, A. BARAN, and M. Balcı, “Synthesis and alpha-Glucosidase and alpha-Amylase Inhibitory Activity Evaluation of Azido-and Aminocyclitols,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 6903–6917, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56968.