Synthesis and evaluation of d-gluco-pyranocyclopropyl amines as potential glucosidase inhibitors

Bioorganic & Medicinal Chemistry Letters
2009.0

Abstract

In the recent past sugar-derived cyclopropylamines were proposed as structurally new glycosidase inhibitors. In this Letter we report our efforts in the synthesis of a set of alpha-glucose configured oxabicyclo[4.1.0] heptanes, based on this hypothesis, bearing an amine substituent on the propyl ring and reveal that their inhibitory potential towards a range of mammalian glucosidases is modest.

Knowledge Graph

Similar Paper

Synthesis and evaluation of d-gluco-pyranocyclopropyl amines as potential glucosidase inhibitors
Bioorganic & Medicinal Chemistry Letters 2009.0
Synthesis and α-glucosidase inhibitory activity evaluation of N-substituted aminomethyl-β-d-glucopyranosides
Bioorganic & Medicinal Chemistry 2013.0
Synthesis of new N-substituted aminoquercitols from naturally available (+)-proto-quercitol and their α-glucosidase inhibitory activity
MedChemComm 2012.0
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
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 and biological evaluation of novel 8-aminomethylated oroxylin A analogues as α-glucosidase inhibitors
Bioorganic & Medicinal Chemistry Letters 2008.0
Synthesis and evaluation of amino-threoses in d- and l-series: Are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?
Bioorganic & Medicinal Chemistry 2007.0
Synthesis and .alpha.-D-glucosidase inhibitory activity of N-substituted valiolamine derivatives as potential oral antidiabetic agents
Journal of Medicinal Chemistry 1986.0
Amine-linked diquercitols as new α-glucosidase inhibitors
Bioorganic & Medicinal Chemistry Letters 2014.0
Synthesis, computational study and glycosidase inhibitory activity of polyhydroxylated conidine alkaloids—a bicyclic iminosugar
Organic & Biomolecular Chemistry 2010.0