Synthesis 2019; 51(21): 4066-4077
DOI: 10.1055/s-0039-1690019
paper
© Georg Thieme Verlag Stuttgart · New York

Bicyclic 1-Azafagomine Derivatives: Synthesis and Glycosidase Inhibitory Testing

Tereza C. Santos Evangelista
a  Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway   Email: emil.lindback@uis.no
b  Department of Organic Chemistry, Chemistry Institute, Federal University of Rio de Janeiro, UFRJ, 21949-900 Rio de Janeiro, RJ, Brazil
,
Óscar Lopéz
c  Departamento 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
a  Department 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
c  Departamento 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
b  Department of Organic Chemistry, Chemistry Institute, Federal University of Rio de Janeiro, UFRJ, 21949-900 Rio de Janeiro, RJ, Brazil
,
Emil Lindbäck
a  Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, 4036 Stavanger, Norway   Email: emil.lindback@uis.no
› Author Affiliations
Spanish MICINN (CTQ2016-78703-P), the Junta de Andalucía (FQM134), the European Regional Development Fund (FEDER) (501100008530), and the University of Stavanger.
Further Information

Publication History

Received: 02 June 2019

Accepted after revision: 12 July 2019

Publication Date:
14 August 2019 (online)

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.

Supporting Information

 
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