Synthesis and glycosidase inhibitory activity of new penta-substituted C8-glycomimetics
The syntheses of new C8-carbasugars and -aminocyclitols related to miglitol and voglibose are described. The key step involves the ring closing metathesis of 1,9-dienes derived from D-mannitol. Chemical transformations of the newly created double bond of the resulting cyclooctenes involved notably hydroboration and reductive amination. The inhibitory activity of the glycomimetics so-obtained has been evaluated towards 24 commercially available glycosidases. (c) 2005 Elsevier Ltd. All rights reserved.
Keywords: carbasuggars ; aminocyclitols ; glycomimetics ; ring closing metathesis ; reductive amination ; glycosidases ; Ring-closing metathesis ; treated niddm patients ; olefin metathesis ; enantiomerically pure ; endoplasmic-reticulum ; diabetes-mellitus ; d-mannitol ; glycosylation ; glucosidase ; acarbose ; Ring-closing metathesis
Univ Paris 05, CNRS, UMR 8601, Lab Chim & Biochim Pharmacol & Toxicol, F-75270 Paris, France. Ecole Polytech Fed Lausanne, Inst Sci & Ingn Chim, BCH, CH-1015 Lausanne, Switzerland.
Record created on 2005-11-09, modified on 2016-08-08