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Synthesis
DOI: 10.1055/s-0043-1773494
paper

N-Alkyl Isofagomine Lactams: Synthesis, Glycosidase Inhibition, and Antimicrobial Assessments

Monika Moreń
a   Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
,
Ana Laura Pereira Lourenço
b   Unitat mixta d’Investigació IRTA-UAB en Sanitat Animal, Centre de Recerca en Sanitat Animal (CReSA), Campus de la Universitat Autònoma de Barcelona (UAB), Bellaterra, 08193, Catalonia, Spain
c   IRTA, Programa de Sanitat Animal, Centre de Recerca en Sanitat Animal (CReSA), Campus de la Universitat Autònoma de Barcelona (UAB), Bellaterra, 08193, Catalonia, Spain
,
Marta Cerdà-Cuéllar
b   Unitat mixta d’Investigació IRTA-UAB en Sanitat Animal, Centre de Recerca en Sanitat Animal (CReSA), Campus de la Universitat Autònoma de Barcelona (UAB), Bellaterra, 08193, Catalonia, Spain
c   IRTA, Programa de Sanitat Animal, Centre de Recerca en Sanitat Animal (CReSA), Campus de la Universitat Autònoma de Barcelona (UAB), Bellaterra, 08193, Catalonia, Spain
,
Karl Kochanowski
b   Unitat mixta d’Investigació IRTA-UAB en Sanitat Animal, Centre de Recerca en Sanitat Animal (CReSA), Campus de la Universitat Autònoma de Barcelona (UAB), Bellaterra, 08193, Catalonia, Spain
c   IRTA, Programa de Sanitat Animal, Centre de Recerca en Sanitat Animal (CReSA), Campus de la Universitat Autònoma de Barcelona (UAB), Bellaterra, 08193, Catalonia, Spain
,
Kåre B. Jørgensen
a   Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
,
Magne O. Sydnes
a   Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
d   Department of Chemistry, Faculty of Science and Technology, University of Bergen, Bergen, Norway
,
Óscar López∗
e   Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Seville, Spain
,
Emil Lindbäck∗
a   Department of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway
› InstitutsangabenA.P. is supported by a European Union Horizon Europe MSCA DN-ID grant (101073263). K.K. is supported by the Spanish Ministry of Research and Innovation (RYC2021-033035-I). M.M., K.B.J., M.O.S, and E.L. are supported by the Universitetet i Stavanger (University of Stavanger). Ó.L. thanks Grant PID2020-116460RB-I00 funded by MCIN/AEI/10.13039/501100011033 for financial support.
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Abstract

A series of six N-alkyl isofagomine lactam derivatives is synthesized over ten steps from d-arabinose. The compounds are evaluated as glycosidase inhibitors. It was found that the N-alkyl groups have a detrimental effect on the glycosidase inhibition activities, as the prepared N-alkyl isofagomine lactam derivatives are much less potent glycosidase inhibitors than native isofagomine lactam.

Key words

azasugar - lactam - glycosidase inhibitor - antimicrobial - synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1773494.
  • Supporting Information


Publikationsverlauf

Eingereicht: 16. Juli 2024

Angenommen nach Revision: 07. Oktober 2024

Artikel online veröffentlicht:
22. Oktober 2024

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