Syntheses and biological investigations of kirkamide and oseltamivir hybrid derivatives

The C7N-aminocyclitol kirkamide was recently isolated from the plant obligate symbiont Candidatus Burkholderia kirkii and was hypothesized to be beneficial to the plant host due to its cytotoxic activity against insects and arthropods. To study its mechanism of action and inspired by its structural...

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Bibliographic Details
Published in:Tetrahedron 2020-12, Vol.76 (51), p.131386, Article 131386
Main Authors: Sieber, Simon, Hsiao, Chien-Chi, Emmanouilidou, Despina, Debowski, Aleksandra W., Stubbs, Keith A., Gademann, Karl
Format: Article
Language:English
Subjects:
Antiviral agents
Glycosidase inhibitors
Natural products
Plant microbe symbiosis
Total synthesis
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Summary:The C7N-aminocyclitol kirkamide was recently isolated from the plant obligate symbiont Candidatus Burkholderia kirkii and was hypothesized to be beneficial to the plant host due to its cytotoxic activity against insects and arthropods. To study its mechanism of action and inspired by its structural similarity with N-acetylglucosamine (GlcNAc) and oseltamivir, kirkamide-oseltamivir hybrid derivatives were synthesized and investigated for their biological activity. Interestingly, kirkamide analogues were reasonably potent against a known bacterial neuraminidase. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131386