Synthesis of new aminocyclitols by selective epoxidation of N-benzyl-N-methyl-2-cyclohepten-1-amine and tert-butyl 4-[benzyl(methyl)amino]-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate

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 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.

show abstract

Synthesis and α‐Glucosidase and α‐Amylase Inhibitory Activity Evaluation of Azido‐ and Aminocyclitols

Aydın

Ally

Aktaş

et al. 2014

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthesis of new aminocyclitols by selective epoxidation of N-benzyl-N-methyl-2-cyclohepten-1-amine and tert-butyl 4-[benzyl(methyl)amino]-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate

Cited by 1 publication

References 7 publications

Synthesis and α‐Glucosidase and α‐Amylase Inhibitory Activity Evaluation of Azido‐ and Aminocyclitols

Synthesis and α‐Glucosidase and α‐Amylase Inhibitory Activity Evaluation of Azido‐ and Aminocyclitols

Contact Info

Product

Resources

About