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

Monika Moreń; Ana Laura Pereira Lourenço; Marta Cerdà-Cuéllar; Karl Kochanowski; Kåre B. Jørgensen; Magne O. Sydnes; Óscar López; Emil Lindbäck

doi:10.1055/s-0043-1773494

Synthesis, Table of Contents

Synthesis 2025; 57(03): 684-694
DOI: 10.1055/s-0043-1773494

paper

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

Monika Moreń

^aDepartment of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway

,

Ana Laura Pereira Lourenço

^bUnitat 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

^cIRTA, 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

^bUnitat 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

^cIRTA, 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

^bUnitat 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

^cIRTA, 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

^aDepartment of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway

,

Magne O. Sydnes

^aDepartment of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway

^dDepartment of Chemistry, Faculty of Science and Technology, University of Bergen, Bergen, Norway

,

Óscar López∗

^eDepartment of Organic Chemistry, Faculty of Chemistry, University of Seville, Seville, Spain

,

Emil Lindbäck∗

^aDepartment of Chemistry, Bioscience and Environmental Engineering, Faculty of Science and Technology, University of Stavanger, Stavanger, Norway

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Abstract

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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

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References

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