Heterocyclic Communications (Apr 2023)

Synthesis and conformational analysis of N-BOC-protected-3,5-bis(arylidene)-4-piperidone EF-24 analogs as anti-cancer agents

  • Smith Robert B.,
  • Roberts William,
  • Upenieks Mary,
  • Gibson Maya Z.,
  • Wentzel Michael T.,
  • Grice Kyle A.,
  • Zingales Sarah K.

DOI
https://doi.org/10.1515/hc-2022-0162
Journal volume & issue
Vol. 29, no. 1
pp. 3376 – 803

Abstract

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Natural products and their analogs have been explored to stop the progression of cancer cells without unwanted side effects. Chalcones, compounds synthesized naturally in plants, have demonstrated potential as anti-cancer treatments. A library of bis-chalcones that are similar in structure to EF-24, a bis-chalcone molecule known to have anti-cancer properties, has been synthesized in order to examine their medicinal properties. This report highlights the synthesis of ten novel analogs, their anti-cancer activities, and conformational analysis via cryo-NMR and corroboration by density functional theory calculations of the lead compound 1b, tert-butyl 3,5-bis((E)-4-methylbenzylidene)-4-oxopiperidine-1-carboxylate.

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