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

Kaszás, Tímea and Szakács, Bence and Bertalan, Márta and Blága, Tekla and Hameed, Faria and Lengyel, Ákos and Saifi, Samreen and Juhászné Tóth, Éva and Fodor-Varga, Luca Anna and Docsa, Tibor and Sipos, Adrienn and Bay, Péter and Kónya-Ábrahám, Anita and Kiss, Attila and Kun, Sándor and Kiss, György Attila and József, János and Juhász, László and Vágvölgyiné Tóth, Marietta (2025) 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. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 26 (17). No.-8167. ISSN 1661-6596

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Abstract

Anhydro-aldose oximes were employed to generate in situ nitrile oxides via a halogenation/base-induced elimination sequence in the presence of NCS and Et3N, 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.

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