Literature

Abstract

Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2 microM, green coffee beans).

DOI： 10.1016/j.bmcl.2004.07.091

Synthesis of 5a-carba-hexopyranoses and hexopyranosylamines, as well as 5a,5a′-dicarbadisaccharides, from 3,8-dioxatricyclo[4.2.1.02,4]nonan-9-ol: glycosidase inhibitory activity of N-substituted 5a-carba-β-gluco- and β-galactopyranosylamines, and derivatives thereof

Bioorganic & Medicinal Chemistry Letters 2004.0

Synthesis of diethyl 4-substituted-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates as a new series of inhibitors against yeast α-glucosidase

European Journal of Medicinal Chemistry 2015.0

Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-d-glucopyranosides

Bioorganic & Medicinal Chemistry 2013.0

The synthesis and biological evaluation of 1-C-alkyl-l-arabinoiminofuranoses, a novel class of α-glucosidase inhibitors

Bioorganic & Medicinal Chemistry Letters 2011.0

Potent glycosidase inhibitors, N-phenyl cyclic isourea derivatives of 5-amino- and 5-amino-1-C-(hydroxymethyl)-cyclopentane-1,2,3,4-tetraols

Bioorganic & Medicinal Chemistry Letters 1994.0

Synthesis of andrographolide derivatives: A new family of α-glucosidase inhibitors