Regioselective Synthesis of 5-Substituted 3-(β-d-Glycopyranosyl)isoxazoles and -isoxazolines by 1,3-Dipolar Cycloaddition as Potential Anticancer Agents and Glycogen Phosphorylase Inhibitors
Anhydro-aldose oximes were employed to generate in situ nitrile oxides via a halogenation/base-induced elimination sequence in the presence of NCS and Et<sub>3</sub>N, which were then used in 1,3-dipolar cycloadditions with alkenes and alkynes to afford 5-substituted 3-(β-d-glycopyranosyl)isoxazole and -isoxazoline derivatives exclusively. These newly synthesized glycomimetics were evaluated for their potential to act as antagonists of A2780 ovarian cancer cells and as inhibitors of glycogen phosphorylase; however, they exhibited no significant activity.
Authors
- Bence Szakács (ORCID: https://orcid.org/0000-0002-9157-3028)
- Marietta Tóth (ORCID: https://orcid.org/0000-0002-4624-038X)
- Adél Lengyel
- Sándor Kun (ORCID: https://orcid.org/0000-0002-0111-390X)
- János József
- Éva Juhász‐Tóth (ORCID: https://orcid.org/0000-0001-7936-8358)
- Attila Kiss‐Szikszai (ORCID: https://orcid.org/0000-0003-3601-5143)
- Tímea Kaszás
- Tekla Blága
- Péter Bai (ORCID: https://orcid.org/0000-0002-6191-6616)
- László Juhász (ORCID: https://orcid.org/0000-0002-7462-7944)
- Anita Ábrahám
- G. Kiss (ORCID: https://orcid.org/0000-0002-6872-916X)
- Adrienn Sipos
- Luca Varga
- Tibor Docsa
- Márta Bertalan
- Faria Hameed
- Samreen Saifi
Institutions
- University of Debrecen (HU)
Publication Details
- Journal
- International Journal of Molecular Sciences
- Published
- 2025-08-22
- DOI
- https://doi.org/10.3390/ijms26178167
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Nemzeti Kutatási Fejlesztési és Innovációs Hivatal