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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-01-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/2/1167 |
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| author | Emily K. Paulin Euphemia Leung Lisa I. Pilkington David Barker |
| author_facet | Emily K. Paulin Euphemia Leung Lisa I. Pilkington David Barker |
| author_sort | Emily K. Paulin |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-03-09T12:24:37Z |
| format | Article |
| id | doaj.art-3796e2cb4a674f3faa1e5abca65cdd8b |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T12:24:37Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-3796e2cb4a674f3faa1e5abca65cdd8b2023-11-30T22:36:23ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-01-01242116710.3390/ijms24021167Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ DerivatisationEmily K. Paulin0Euphemia Leung1Lisa I. Pilkington2David Barker3School of Chemical Sciences, University of Auckland, Auckland 1010, New ZealandAuckland Cancer Society Research Centre, University of Auckland, Auckland 1023, New ZealandSchool of Chemical Sciences, University of Auckland, Auckland 1010, New ZealandSchool of Chemical Sciences, University of Auckland, Auckland 1010, New ZealandDibenzylbutyrolactone 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.https://www.mdpi.com/1422-0067/24/2/1167lignansdibenzylbutyrolactonearctigeninprodrugsanti-proliferative |
| spellingShingle | Emily K. Paulin Euphemia Leung Lisa I. Pilkington David Barker Synthesis and Anti-Proliferative Evaluation of Arctigenin Analogues with C-9′ Derivatisation International Journal of Molecular Sciences lignans dibenzylbutyrolactone arctigenin prodrugs anti-proliferative |
| 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 | lignans dibenzylbutyrolactone arctigenin prodrugs anti-proliferative |
| url | https://www.mdpi.com/1422-0067/24/2/1167 |
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