TY - JOUR
T1 - Synthesis of Bio-Inspired 1,3-Diarylpropene Derivatives via Heck Cross-Coupling and Cytotoxic Evaluation on Breast Cancer Cells
AU - Tan, Aik Sian
AU - Singh, Jaymeer
AU - Rezali, Nurul Syafiqah
AU - Muhamad, Musthahimah
AU - Nik Mohamed Kamal, Nik Nur Syazni
AU - Six, Yvan
AU - Azmi, Mohamad Nurul
N1 - Publisher Copyright:
© 2022 by the authors.
PY - 2022/9/1
Y1 - 2022/9/1
N2 - 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).
AB - 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).
KW - 1,3-diarylpropene
KW - Heck cross-coupling
KW - breast cancer cells
KW - cytotoxic effects
KW - β-hydride elimination
U2 - 10.3390/molecules27175373
DO - 10.3390/molecules27175373
M3 - Article
C2 - 36080141
AN - SCOPUS:85137601832
SN - 1420-3049
VL - 27
JO - Molecules
JF - Molecules
IS - 17
M1 - 5373
ER -
