N-2 Alkylated analogues of aza-galactofagomine as potential inhibitors of β-glucosidase

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Published: Jun 17, 2024
DOI: https://doi.org/10.2298/JSC240315062D
Keywords:
iminosugars glycosidase inhibitor Gaucher’s disease

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Filip Đurković
University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia
https://orcid.org/0000-0003-1507-1277
Mario Zlatović
University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia
https://orcid.org/0000-0003-4311-1731
Dušan Sladić
University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia
https://orcid.org/0000-0002-1000-9813
Irena Novaković
University of Belgrade – Institute of Chemistry, Technology and Metallurgy, Njegoševa 12, Belgrade, Serbia
https://orcid.org/0000-0001-9881-1204
Filip Bihelović
University of Belgrade - Faculty of Chemistry, Studenstki trg 12-16, Belgrade, Serbia
https://orcid.org/0000-0002-7654-3189
Zorana Ferjančić
Faculty of Chemistry, Departmet of Organic Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrad, Serbia
https://orcid.org/0000-0001-5932-629X

Abstract

The synthesis of four N-2-alkylated aza-galactofagomine (AGF) analogues was achieved by intermolecular reductive hydrazination or alkylation of suitably protected AGF. The synthesized compounds were evaluated as potential β-glucosidase inhibitors. The preliminary screening of inhibitor activity, conducted with sweet almond β-glucosidase immobilized in agar, as well as the standard inhibition assay with the same enzyme, showed inhibitory potency of the synthesized analogues. In addition, these results are in a good agreement with docking analysis of the human acid β-glucosidase, the enzyme implicated in Gaucher's disease.

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[1]
F. . Đurković, M. Zlatović, D. . Sladić, I. Novaković, F. . Bihelović, and Z. Ferjančić, “N-2 Alkylated analogues of aza-galactofagomine as potential inhibitors of β-glucosidase”, J. Serb. Chem. Soc., Jun. 2024.
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Organic Chemistry
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