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Bioorg Med Chem. 2006 Sep 15;14(18):6255-82. Epub 2006 Jun 22.

Search for alpha-glucosidase inhibitors: new N-substituted valienamine and conduramine F-1 derivatives.

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  • 1Laboratoire de glycochimie et de synthèse asymétrique, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC, BCH, CH-1015 Lausanne-Dorigny, Switzerland.

Abstract

A solid-phase synthesis of new N-substituted valienamines has been developed and new synthesis of (+/-)-conduramine F-1, (-)-conduramine F-1, and (+)-ent-conduramine F-1 is presented, together with the preparation of N-benzylated conduramines F-1. N-Benzylation of both valienamine and (+)-ent-conduramine F-1 improves their inhibitory activity toward alpha-glucosidases significantly. The additional hydroxymethyl group makes valienamine derivatives more active than their (+)-ent-conduramine F-1 analogues.

PMID:
16797996
[PubMed - indexed for MEDLINE]
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