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Synthesis and glycosidase inhibitory activity of new penta-substituted C8-glycomimetics |
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| Authors: | Olivia Andriuzzi Pierre Vogel |
| Affiliation: | a Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, Université René Descartes, UMR 8601 CNRS, 45 rue des Saints-Pères, 75270 Paris Cedex 06, France b Institut des Sciences et Ingéniérie Chimiques, Ecole Polytechnique Fédérale de Lausanne, BCH, CH-1015 Lausanne, Switzerland |
| Abstract: | 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. |
| Keywords: | Carbasugars Aminocyclitols Glycomimetics Ring closing metathesis Reductive amination Glycosidases |
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