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Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation
Dibenzylbutyrolactone lignans (DBLs) are a class of natural products with a wide variety of biological activities. Due to their potential for the development of human therapeutic agents, DBLs have been subjected to various SAR studies in order to optimise activity. Previous reports have mainly consi...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9866048/ https://www.ncbi.nlm.nih.gov/pubmed/36674683 http://dx.doi.org/10.3390/ijms24021167 |
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author | Paulin, Emily K. Leung, Euphemia Pilkington, Lisa I. Barker, David |
author_facet | Paulin, Emily K. Leung, Euphemia Pilkington, Lisa I. Barker, David |
author_sort | Paulin, Emily K. |
collection | PubMed |
description | Dibenzylbutyrolactone lignans (DBLs) are a class of natural products with a wide variety of biological activities. Due to their potential for the development of human therapeutic agents, DBLs have been subjected to various SAR studies in order to optimise activity. Previous reports have mainly considered changes on the aromatic rings and at the benzylic carbons of the compounds, whilst the effects of substituents in the lactone, at the C-9′ position, have been relatively unexplored. This position has an unexploited potential for the development of novel dibenzyl butyrolactone derivatives, with previous preliminary findings revealing C-9′-hydroxymethyl analogues inducing programmed cell cycle death. Using the core structure of the bioactive natural product arctigenin, C-9′ derivatives were synthesised using various synthetic pathways and with prepared derivatives providing more potent anti-proliferative activity than the C-9′-hydroxymethyl lead compound. |
format | Online Article Text |
id | pubmed-9866048 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-98660482023-01-22 Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation Paulin, Emily K. Leung, Euphemia Pilkington, Lisa I. Barker, David Int J Mol Sci Article Dibenzylbutyrolactone lignans (DBLs) are a class of natural products with a wide variety of biological activities. Due to their potential for the development of human therapeutic agents, DBLs have been subjected to various SAR studies in order to optimise activity. Previous reports have mainly considered changes on the aromatic rings and at the benzylic carbons of the compounds, whilst the effects of substituents in the lactone, at the C-9′ position, have been relatively unexplored. This position has an unexploited potential for the development of novel dibenzyl butyrolactone derivatives, with previous preliminary findings revealing C-9′-hydroxymethyl analogues inducing programmed cell cycle death. Using the core structure of the bioactive natural product arctigenin, C-9′ derivatives were synthesised using various synthetic pathways and with prepared derivatives providing more potent anti-proliferative activity than the C-9′-hydroxymethyl lead compound. MDPI 2023-01-06 /pmc/articles/PMC9866048/ /pubmed/36674683 http://dx.doi.org/10.3390/ijms24021167 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Paulin, Emily K. Leung, Euphemia Pilkington, Lisa I. Barker, David Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation |
title | Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation |
title_full | Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation |
title_fullStr | Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation |
title_full_unstemmed | Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation |
title_short | Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation |
title_sort | synthesis and anti-proliferative evaluation of arctigenin analogues with c-9′ derivatisation |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9866048/ https://www.ncbi.nlm.nih.gov/pubmed/36674683 http://dx.doi.org/10.3390/ijms24021167 |
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