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Article Dans Une Revue Tetrahedron Année : 2005

Short synthesis of new salacinol analogues and their evaluation as glycosidase inhibitors

M. Benazza
G. Demailly
  • Fonction : Auteur

Résumé

Versatile synthesis of some analogues of the naturally-occurring α-glucosidase inhibitor salacinol (1), involving thioanhydro alditol moieties with erythro, d,l-threo, xylo, ribo, d-arabino and d-manno configurations is described. Nucleophilic attack at the least-hindered carbon atom of an l- or d-protected erythritol cyclic sulfate by the thioanhydro alditol sulfur atom yielded the desired zwitterionic compounds. In addition, the preparation of the cyclic sulfates of 2,4-O-benzylidene-d-erythritol and 2,4-O-isopropylidene-l-erythritol was improved. Enzyme inhibition tests showed that most of the new compounds were weak but specific inhibitors, while good inhibitory activity was found for a six-membered ring analogue (β-glucosidase: Ki=16 μM)
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Dates et versions

hal-00125713 , version 1 (02-03-2007)

Identifiants

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Estelle Gallienne, M. Benazza, G. Demailly, Jean Bolte, Marielle Lemaire. Short synthesis of new salacinol analogues and their evaluation as glycosidase inhibitors. Tetrahedron, 2005, pp.4557-4568. ⟨10.1016/j.tet.2005.03.015⟩. ⟨hal-00125713⟩
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