| Autor: |
Tan AS; School of Chemical Sciences, Universiti Sains Malaysia, Gelugor 11800, Penang, Malaysia., Singh J; School of Chemical Sciences, Universiti Sains Malaysia, Gelugor 11800, Penang, Malaysia., Rezali NS; Chemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, Gelugor 11800, Penang, Malaysia., Muhamad M; Integrative Medicine Cluster, Advanced Medical and Dental Institute, Universiti Sains Malaysia, Kepala Batas 13200, Penang, Malaysia., Nik Mohamed Kamal NNS; Integrative Medicine Cluster, Advanced Medical and Dental Institute, Universiti Sains Malaysia, Kepala Batas 13200, Penang, Malaysia., Six Y; Laboratoire de Synthèse Organique (LSO), École Polytechnique, CNRS, Institut Polytechnique de Paris, CEDEX, 91128 Palaiseau, France., Azmi MN; School of Chemical Sciences, Universiti Sains Malaysia, Gelugor 11800, Penang, Malaysia. |
| Abstrakt: |
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 (E) 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 7d exhibited weak cytotoxic activity towards MCF-7 cell lines with IC50 values of 47.92 µM in comparison with tamoxifen and was considered to have general toxicity (SI value < 2). |
