Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans

Samuel Davidson, Lisa Pilkington, Nina Dempsey-Hibbert, MOHAMED EL MOHTADI, shiying Tang, Thomas Wainwright, Kathryn Whitehead, David Barker*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)
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Abstract

Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.
Original languageEnglish
Article number3057
JournalMolecules
Volume23
Issue number12
Early online date22 Nov 2018
DOIs
Publication statusPublished - 22 Nov 2018

Keywords

  • lignans
  • dibenzyl butyrolactones
  • anti-proliferative
  • acyl-Claisen
  • stereoselective synthesis

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