Synthesis of cytotoxic spirocyclic imides from a biomass-derived oxanorbornene

Synthesis of cytotoxic spirocyclic imides from a biomass-derived oxanorbornene

N-Substituted derivatives of cantharimide and norcantharimide represent a promising but underutilized motif for therapeutic applications. Herein, we report a divergent strategy for the preparation of secondary amides and norcantharimide-resembling spirocyclic imides from a biomass-derived oxanorborn...

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Veröffentlicht in:Tetrahedron 2021-01, Vol.77, p.131754, Article 131754
Hauptverfasser: Lawrenson, Stefan B., Pearce, Amanda K., Hart, Sam, Whitwood, Adrian C., O’Reilly, Rachel K., North, Michael
Format: Artikel
Sprache:eng
Schlagworte:
Active surfactants
Cantharidin
Cytotoxicity
Drug design
Spirocyclic
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Zusammenfassung:N-Substituted derivatives of cantharimide and norcantharimide represent a promising but underutilized motif for therapeutic applications. Herein, we report a divergent strategy for the preparation of secondary amides and norcantharimide-resembling spirocyclic imides from a biomass-derived oxanorbornene and assess their biological activity. Computational modelling suggests these compounds fall perfectly within lead-like chemical space (200 Da 
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131754