Spirocyclopropyl pyrrolidines as a new series of alpha-L-fucosidase inhibitors.
ABSTRACT 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 alpha-L-fucosidase from bovine kidney (Ki=1.6 microM, competitive).
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ABSTRACT: The transformation can be achieved by heating substrates (I) in DMSO without the need for any catalyst or additional reagent.Synlett. 03/2013; 24(07):827-830.
- Synthesis. 08/2011; 2011(18):3015-3019.
- Tetrahedron 01/2010; 66:15. · 2.82 Impact Factor