Cycloadditions of Sugar-Derived Nitrones Targeting Polyhydroxylated Indolizidines

Year: 2016

Authors: Martella D., D’Adamio G., Parmeggiani C., Cardona F., Moreno-Clavijo E., Robina I., Goti A.

Autors Affiliation: Univ Florence, Dept Chem Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, Italy; CNR INO UOS Sesto Fiorentino, Via N Carrara 1, I-50019 Sesto Fiorentino, FI, Italy; LENS, Via N Carrara 1, I-50019 Sesto Fiorentino, FI, Italy; Univ Seville, Fac Quim, Dept Quim Organ, C Prof Garcia Gonzalez 1, E-41012 Seville, Spain.

Abstract: The 1,3 dipolar cycloaddition reactions of three pentose-derived pyrroline N-oxides with mono-and disubstituted alkenes are reported. A strong dependence of the diastereoselectivity of the cycloadditions on the relative configuration of the nitrone stereocentres was observed. Further transformation of the reaction products allowed the synthesis of four new tetrahydroxylated indolizidines. Their activity as glycosidase inhibitors was evaluated against a panel of commercially available glycosidases. The specificity of inhibitory activity against amyloglucosidase and alpha-mannosidases depends on the configuration at C-2 of the indolizidine moiety.

Journal/Review: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Volume: 2016 (8)      Pages from: 1588  to: 1598

More Information: The authors thank the Ministero dell’Universita e della Ricerca (MIUR), Italy (PRIN 2010-2011, 2010L9SH3K 006), the Ministero della Salute, Regione Toscana (Ricerca Finalizzata, RF-2011-02347694), and the Ente Cassa di Risparmio di Firenze for financial support. The Ministerio de Economia y Competitividad (MEC), Spain (CTQ 2012-31247) is also acknowledged for financial support. Prof. A. Morrone and Dr. S. Catarzi (Meyer’s Children Hospital in Florence) are thanked for biological data on human lysosomal mannosidase.
KeyWords: Cycloaddition; Diastereoselectivity; Carbohydrates; Nitrogen heterocycles; Nitrones; Inhibitors
DOI: 10.1002/ejoc.201501427

Citations: 23
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