The synthesis of three tetrahydroxyindolizidines and one tetrahydroxypyrrolizidine related to natural hyacinthacines B and their biological evaluation as glycosidase inhibitors is reported. The target molecules were obtained through highly stereoselective cycloadditions between sugriched allylic and homoallylic alcohols. This allowed the installation of a methyl group at C5 – a common feature of many natural hyacinthacines – with high control over the stereoselectivity. The new compounds inhibit amyloglucosidase from Aspergillus niger and β-glucosidase from almonds. Compound 1 is a competitive inhibitor of amyloglucosidase and shows a fair selectivity towards this enzyme. The presence of C5-Me substitution in indolizidines 2 and 3 slightly diminishes the inhibitory activity towards amyloglucosidase whereas it improves the inhibitory properties towards β-glucosidase.

Synthesis and Glycosidase Inhibition Studies of 5-Methyl-Substituted Tetrahydroxyindolizidines and -pyrrolizidines Related to Natural Hyacinthacines B / Daniele Martella; Francesca Cardona; Camilla Parmeggiani; Francisco Franco; Juan A. Tamayo; Inmaculada Robina; Elena Moreno-Clavijo; Antonio J. Moreno-Vargas; Andrea Goti. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - (2013), pp. 4047-4056. [10.1002/ejoc.201300103]

Synthesis and Glycosidase Inhibition Studies of 5-Methyl-Substituted Tetrahydroxyindolizidines and -pyrrolizidines Related to Natural Hyacinthacines B

MARTELLA, DANIELE;CARDONA, FRANCESCA;PARMEGGIANI, CAMILLA;GOTI, ANDREA
2013

Abstract

The synthesis of three tetrahydroxyindolizidines and one tetrahydroxypyrrolizidine related to natural hyacinthacines B and their biological evaluation as glycosidase inhibitors is reported. The target molecules were obtained through highly stereoselective cycloadditions between sugriched allylic and homoallylic alcohols. This allowed the installation of a methyl group at C5 – a common feature of many natural hyacinthacines – with high control over the stereoselectivity. The new compounds inhibit amyloglucosidase from Aspergillus niger and β-glucosidase from almonds. Compound 1 is a competitive inhibitor of amyloglucosidase and shows a fair selectivity towards this enzyme. The presence of C5-Me substitution in indolizidines 2 and 3 slightly diminishes the inhibitory activity towards amyloglucosidase whereas it improves the inhibitory properties towards β-glucosidase.
2013
4047
4056
Daniele Martella; Francesca Cardona; Camilla Parmeggiani; Francisco Franco; Juan A. Tamayo; Inmaculada Robina; Elena Moreno-Clavijo; Antonio J. Moreno-Vargas; Andrea Goti
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/822912
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