Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells
The Heck cross-coupling reaction is a well-established chemical tool for the synthesis of unsaturated compounds by formation of a new C-C bond. In this study, 1,3-diarylpropene derivatives, designed as structural analogues of stilbenoids and dihydrostilbenoids, were synthesised by the palladium-cata...
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2022-08-01
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| author | Aik Sian Tan Jaymeer Singh Nurul Syafiqah Rezali Musthahimah Muhamad Nik Nur Syazni Nik Mohamed Kamal Yvan Six Mohamad Nurul Azmi |
| author_facet | Aik Sian Tan Jaymeer Singh Nurul Syafiqah Rezali Musthahimah Muhamad Nik Nur Syazni Nik Mohamed Kamal Yvan Six Mohamad Nurul Azmi |
| author_sort | Aik Sian Tan |
| collection | DOAJ |
| description | The Heck cross-coupling reaction is a well-established chemical tool for the synthesis of unsaturated compounds by formation of a new C-C bond. In this study, 1,3-diarylpropene derivatives, designed as structural analogues of stilbenoids and dihydrostilbenoids, were synthesised by the palladium-catalysed reactions of 2-amidoiodobenzene derivatives with either estragole or eugenol. The products were obtained with high (<i>E</i>) stereoselectivity but as two regioisomers. The ratios of isomers were found to be dependent on the nature of the allylbenzene partner and were rationalised by electronic effects exercising a determining influence in the β-hydride elimination step. In addition, the cytotoxic effects of all the Heck reaction products were evaluated against MCF-7 and MDA-MB-231 human breast cancer cells, with unpromising results. Among all, compound <b>7d</b> exhibited weak cytotoxic activity towards MCF-7 cell lines with IC<sub>50</sub> values of 47.92 µM in comparison with tamoxifen and was considered to have general toxicity (SI value < 2). |
| first_indexed | 2024-03-10T01:31:41Z |
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| id | doaj.art-7562ba07541842b082e14892ac0bee8c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:31:41Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
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| spelling | doaj.art-7562ba07541842b082e14892ac0bee8c2023-11-23T13:40:52ZengMDPI AGMolecules1420-30492022-08-012717537310.3390/molecules27175373Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer CellsAik Sian Tan0Jaymeer Singh1Nurul Syafiqah Rezali2Musthahimah Muhamad3Nik Nur Syazni Nik Mohamed Kamal4Yvan Six5Mohamad Nurul Azmi6School of Chemical Sciences, Universiti Sains Malaysia, Gelugor 11800, Penang, MalaysiaSchool of Chemical Sciences, Universiti Sains Malaysia, Gelugor 11800, Penang, MalaysiaChemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, Gelugor 11800, Penang, MalaysiaIntegrative Medicine Cluster, Advanced Medical and Dental Institute, Universiti Sains Malaysia, Kepala Batas 13200, Penang, MalaysiaIntegrative Medicine Cluster, Advanced Medical and Dental Institute, Universiti Sains Malaysia, Kepala Batas 13200, Penang, MalaysiaLaboratoire de Synthèse Organique (LSO), École Polytechnique, CNRS, Institut Polytechnique de Paris, CEDEX, 91128 Palaiseau, FranceSchool of Chemical Sciences, Universiti Sains Malaysia, Gelugor 11800, Penang, MalaysiaThe Heck cross-coupling reaction is a well-established chemical tool for the synthesis of unsaturated compounds by formation of a new C-C bond. In this study, 1,3-diarylpropene derivatives, designed as structural analogues of stilbenoids and dihydrostilbenoids, were synthesised by the palladium-catalysed reactions of 2-amidoiodobenzene derivatives with either estragole or eugenol. The products were obtained with high (<i>E</i>) stereoselectivity but as two regioisomers. The ratios of isomers were found to be dependent on the nature of the allylbenzene partner and were rationalised by electronic effects exercising a determining influence in the β-hydride elimination step. In addition, the cytotoxic effects of all the Heck reaction products were evaluated against MCF-7 and MDA-MB-231 human breast cancer cells, with unpromising results. Among all, compound <b>7d</b> exhibited weak cytotoxic activity towards MCF-7 cell lines with IC<sub>50</sub> values of 47.92 µM in comparison with tamoxifen and was considered to have general toxicity (SI value < 2).https://www.mdpi.com/1420-3049/27/17/5373Heck cross-coupling1,3-diarylpropeneβ-hydride eliminationcytotoxic effectsbreast cancer cells |
| spellingShingle | Aik Sian Tan Jaymeer Singh Nurul Syafiqah Rezali Musthahimah Muhamad Nik Nur Syazni Nik Mohamed Kamal Yvan Six Mohamad Nurul Azmi Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells Molecules Heck cross-coupling 1,3-diarylpropene β-hydride elimination cytotoxic effects breast cancer cells |
| title | Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells |
| title_full | Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells |
| title_fullStr | Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells |
| title_full_unstemmed | Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells |
| title_short | Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells |
| title_sort | synthesis of bio inspired 1 3 diarylpropene derivatives via heck cross coupling and cytotoxic evaluation on breast cancer cells |
| topic | Heck cross-coupling 1,3-diarylpropene β-hydride elimination cytotoxic effects breast cancer cells |
| url | https://www.mdpi.com/1420-3049/27/17/5373 |
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