Next Article in Journal
On the Mechanism of Action of Anti-Inflammatory Activity of Hypericin: An In Silico Study Pointing to the Relevance of Janus Kinases Inhibition
Next Article in Special Issue
Targeted Lignan Profiling and Anti-Inflammatory Properties of Schisandra rubriflora and Schisandra chinensis Extracts
Previous Article in Journal
Sodium Phenylbutyrate Ameliorates Inflammatory Response Induced by Staphylococcus aureus Lipoteichoic Acid via Suppressing TLR2/NF-κB/NLRP3 Pathways in MAC-T Cells
Previous Article in Special Issue
Concise Synthesis of (+)-β- and γ-Apopicropodophyllins, and Dehydrodesoxypodophyllotoxin
Article Menu
Issue 12 (December) cover image

Export Article

Open AccessArticle

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

1
School of Chemical Sciences, University of Auckland, Aucklamd 1010, New Zealand
2
School of Healthcare Science, Manchester Metropolitan University, Manchester M1 5GD, UK
3
The MacDiarmid Institute for Advanced Materials and Nanotechnology, Wellington 6140, New Zealand
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(12), 3057; https://doi.org/10.3390/molecules23123057
Received: 12 November 2018 / Revised: 20 November 2018 / Accepted: 21 November 2018 / Published: 22 November 2018
(This article belongs to the Special Issue Lignans)
  |  
PDF [1800 KB, uploaded 28 November 2018]
  |  

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. View Full-Text
Keywords: lignans; dibenzyl butyrolactones; anti-proliferative; acyl-Claisen; stereoselective synthesis lignans; dibenzyl butyrolactones; anti-proliferative; acyl-Claisen; stereoselective synthesis
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary material

SciFeed
Printed Edition Available!
A printed edition of this Special Issue is available here.

Share & Cite This Article

MDPI and ACS Style

Davidson, S.J.; Pilkington, L.I.; Dempsey-Hibbert, N.C.; El-Mohtadi, M.; Tang, S.; Wainwright, T.; Whitehead, K.A.; Barker, D. Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans. Molecules 2018, 23, 3057.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top