Spirocyclopropyl pyrrolidines as a new series of α- l-fucosidase inhibitors
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...
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Published in | Bioorganic & medicinal chemistry Vol. 14; no. 12; pp. 4047 - 4054 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Elsevier Ltd
15.06.2006
Elsevier Science |
Subjects | |
Online Access | Get full text |
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Summary: | 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). |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0968-0896 1464-3391 |
DOI: | 10.1016/j.bmc.2006.02.005 |