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From the same journal

Synthesis of cytotoxic spirocyclic imides from a biomass-derived oxanorbornene

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  • Stefan B. Lawrenson
  • Amanda K. Pearce
  • Sam Hart
  • Adrian C. Whitwood
  • Rachel K. O'Reilly
  • Michael North


Publication details

DateAccepted/In press - 6 Nov 2020
DateE-pub ahead of print - 12 Nov 2020
DatePublished (current) - 1 Jan 2021
Number of pages12
Early online date12/11/20
Original languageEnglish


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 < RMM < 350 Da, −1 < AlogP < 3), with the spirocyclic imides preferred due to their lack of reactive functionalities. Biological analysis of the spirocyclic imides revealed that the compounds displayed antiproliferative activity against a range of human cancer cells (A549, HCT 116, OVCAR-3, MDA-MB-231, MCF7 and PC-3) with the N-octyl derivative displaying the greatest potential as a potent broad-spectrum anticancer drug. Dose-response curves for the N-octyl spirocyclic imide found EC50 values of 56–95 μM dependent on the cell line, with highest activity against human colorectal carcinoma cells (HCT 116).

Bibliographical note

© 2020 Elsevier Ltd. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

    Research areas

  • Active surfactants, Cantharidin, Cytotoxicity, Drug design, Spirocyclic

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