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Issue 4, 2015
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Synthesis of isoxazolidine-containing uridine derivatives as caprazamycin analogues

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Abstract

Simplification of caprazamycins, which are promising antibacterial nucleoside natural products, was conducted by scaffold-hopping of the structurally complex diazepanone moiety to the isoxazolidine scaffold. The designed isoxazolidine-containing uridine derivatives were synthesized by an intramolecular 1,3-dipolar cycloaddition of alkenyl nitrone as a key step. The lactone-fused isoxazolidine intermediate was easily converted to the target compounds by sequential introduction of key substituents upon ring-opening the lactone moiety by nucleophilic substitution and electrophilic capping of the resulting primary alcohol. Several analogues exhibited good activity against H. influenzae ATCC 10211 (MIC 0.25–0.5 μg mL−1) and moderate activity against vancomycin-resistant E. faecalis SR7914 (MIC 4–8 μg mL−1).

Graphical abstract: Synthesis of isoxazolidine-containing uridine derivatives as caprazamycin analogues

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Publication details

The article was received on 08 Oct 2014, accepted on 14 Nov 2014 and first published on 14 Nov 2014


Article type: Paper
DOI: 10.1039/C4OB02142H
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Org. Biomol. Chem., 2015,13, 1187-1197

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    Synthesis of isoxazolidine-containing uridine derivatives as caprazamycin analogues

    M. Yamaguchi, A. Matsuda and S. Ichikawa, Org. Biomol. Chem., 2015, 13, 1187
    DOI: 10.1039/C4OB02142H

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