Spirocyclopropyl pyrrolidines as a new series of α-l-fucosidase inhibitors
| Autor: | Philippe Bertus, Pierre Vogel, Christophe R. Laroche, Catherine Schütz, Jean-Bernard Behr, Richard Plantier-Royon, Jan Szymoniak |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
Pyrrolidines
Stereochemistry Clinical Biochemistry Molecular Conformation Pharmaceutical Science Kidney Biochemistry Chemical synthesis Structure-Activity Relationship chemistry.chemical_compound Drug Discovery Animals Spiro Compounds Fucosidase Enzyme Inhibitors Molecular Biology alpha-L-Fucosidase chemistry.chemical_classification Heptane Bicyclic molecule biology Organic Chemistry Stereoisomerism In vitro Enzyme chemistry Enzyme inhibitor biology.protein Molecular Medicine Cattle Selectivity |
| Zdroj: | Bioorganic & Medicinal Chemistry. 14:4047-4054 |
| ISSN: | 0968-0896 |
| Popis: | Polyhydroxy 4-azaspiro[2.4]heptane derivatives (spirocyclopropyl iminosugars) were prepared in four to six steps from readily available protected aldoses. The key step of the reaction sequence involves a titanium-mediated aminocyclopropanation of glycononitriles with subsequent cyclization. Five new polyhydroxypyrrolidines so-obtained have been evaluated for their ability to inhibit 16 glycosidases. One of them exhibits selective inhibition of α- l -fucosidase from bovine kidney ( K i = 1.6 μM, competitive). |
| Databáze: | OpenAIRE |
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