Bioorganic & Medicinal Chemistry 2010-04-01

Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors

Wojciech Schönemann, Estelle Gallienne, Philippe Compain, Kyoko Ikeda, Naoki Asano, Olivier R. Martin

Index: Bioorg. Med. Chem. 18(7) , 2645-50, (2010)

Full Text: HTML

Abstract

A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-l-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the d-gluco and d-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity.Copyright 2010 Elsevier Ltd. All rights reserved.