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■ Synthesis of New Pyrrolidine Derivatives as Inhibitors of α-Mannosidase and of the Growth of Human Glioblastoma Cells

Sylvain Favre, Hélène Fiaux, Catherine Schütz, Pierre Vogel, Lucienne Juillerat-Jeanneret,* and Sandrine Gerber-Lemaire*

*Laboratory of Glycochemistry and Asymmetric Synthesis, Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime (BCH), CH-1015 Lausanne, Switzerland

Abstract

New 2-benzylamino-3,4-dihydroxypyrrolidines bearing aromatic and aliphatic amido side chains have been prepared. The influence of the amido substituents on the inhibitory activity of these diamines toward 24 commercially available glycosidases was determined. The most potent and selective α-mannosidase inhibitor (6d) (N-[(2R)-2-({[(2R,3R,4S)-3,4-dihydroxypyrrolidin -2-yl]methyl} amino)-2-phenylethyl]-3-bromobenzamide) of these series was also the most potent inhibitor of the growth of human glioblastoma cells.