Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues.

Basic Information

ID: ALA1147832

Journal: Bioorg Med Chem Lett

Title: Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues.

Authors: Pearson MS, Saad RO, Dintinger T, Amri H, Mathé-Allainmat M, Lebreton J.

Abstract: Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient glycosidase inhibitory effects. The syntheses and biological evaluation of two new series of 5-deoxyadenophorine analogues in their racemic form are reported. The compounds 12e and 13d bearing a C11 and C7 alkyl chain, respectively, were found to be potent inhibitors of the beta-glucosidase from almond with Ki near to 60 microM. The compounds 13a,d which possess a 3,4-cis stereochemistry were efficient on glucosidases but also on the beta-galactosidase, what was not observed with the 3,4-trans series 12.

CiteXplore: 16603357

DOI: 10.1016/j.bmcl.2006.03.035

Patent ID: