Amine-linked diquercitols as new α-glucosidase inhibitors

Wisuttaya Worawalai; Sumrit Wacharasindhu; Preecha Phuwapraisirisan

doi:10.1016/j.bmcl.2014.09.064

Amine-linked diquercitols as new α-glucosidase inhibitors

Bioorg Med Chem Lett. 2014 Dec 1;24(23):5530-3. doi: 10.1016/j.bmcl.2014.09.064. Epub 2014 Oct 6.

Authors

Wisuttaya Worawalai¹, Sumrit Wacharasindhu¹, Preecha Phuwapraisirisan²

Affiliations

¹ Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand.
² Natural Products Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand. Electronic address: preecha.p@chula.ac.th.

PMID: 25451999
DOI: 10.1016/j.bmcl.2014.09.064

Abstract

Two new diastereomeric amine-linked diquercitols 7 and 8 were synthesized by reductive amination of ketoquercitol 4 and epimeric aminoquercitols 3 and 6. The ketone and amines were successfully prepared, without the formation of byproducts, from naturally available (+)-proto-quercitol (1). The amine-linked diquercitols showed inhibitory effect against α-glucosidases with more pronounced potency than their original aminoquercitol monomers.

Keywords: Aminocyclitol; Diabetes; Glucosidase; Quercitol; Reductive amination.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Drug Resistance
Enzyme Inhibitors / pharmacology*
Molecular Structure
Structure-Activity Relationship
alpha-Glucosidases / metabolism*

Substances

Enzyme Inhibitors
alpha-Glucosidases