Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing

Tereza C. Santos Evangelista; Óscar Lopéz; Magne O. Sydnes; José G. Fernández-Bolaños; Sabrina Baptista Ferreira; Emil Lindbäck

doi:10.1055/s-0039-1690019

Synthesis, Table of Contents

Synthesis 2019; 51(21): 4066-4077
DOI: 10.1055/s-0039-1690019

paper

Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing

Tereza C. Santos Evangelista

^aDepartment of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway Email: emil.lindback@uis.no

^bDepartment of Organic Chemistry, Chemistry Institute, Federal University of Rio de Janeiro, UFRJ, 21949-900 Rio de Janeiro, RJ, Brazil

,

Óscar Lopéz∗

^cDepartamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, c/Profesor García González 1, 41012 Seville, Spain Email: osc-lopez@us.es

,

Magne O. Sydnes

^aDepartment of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway Email: emil.lindback@uis.no

,

José G. Fernández-Bolaños

^cDepartamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, c/Profesor García González 1, 41012 Seville, Spain Email: osc-lopez@us.es

,

Sabrina Baptista Ferreira

^bDepartment of Organic Chemistry, Chemistry Institute, Federal University of Rio de Janeiro, UFRJ, 21949-900 Rio de Janeiro, RJ, Brazil

,

Emil Lindbäck∗

^aDepartment of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway Email: emil.lindback@uis.no

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Abstract

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Abstract

The synthesis of a series of 1-azafagomine derivatives that are tethered with five- and six-membered 1,2-annulated ring systems is described. These compounds were used in order to explore whether a hydrogen-bond acceptor group on the carbon atom corresponding to the glycosidic oxygen is able to interact with the catalytic acidic residue of β-glucosidase. The hydrogen-bond acceptor group was installed at various positions on the annulated ring system making it possible to study the effect of altering the position of this group.

Key words

iminosugars - glycosidases - glycosidase inhibitor - hydrogen bond - hydrogen bond acceptor - catalytic acidic residue

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References

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