ABSTRACT
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 ß-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).
Subject(s)
Antineoplastic Agents , Breast Neoplasms , Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Cell Line, Tumor , Cell Proliferation , Drug Screening Assays, Antitumor , Female , Humans , MCF-7 Cells , Palladium/chemistry , Palladium/pharmacology , Structure-Activity Relationship , Tamoxifen/pharmacologyABSTRACT
Several Magnolia species have exhibited potent biological activities such as anti-inflammatory, anti-angiogenesis, anticonvulsant, anti-obesity, and antiviral activities. However, the Magnolia candollii from Malaysia has not been investigated yet. Hence, this study aims to investigate the chemical composition and bioactivities of the essential oil of Magnolia candollii H.Keng from Malaysia. The hydrodistillation process was used to produce the essential oil, and gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) were used to analyse it. In total, 44 chemical components were identified in the bark oil, accounting for 98.4%. The major components of the essential oil were α-pinene (29.7%), elemol (10.2%), ß-pinene (8.5%), ß-caryophyllene (7.2%), α-terpineol (7.0%), guaiol (5.4%), and bulnesol (4.9%). Acetylcholinesterase and anti-inflammatory activities were also evaluated using the Ellman method and lipoxygenase enzyme, respectively, in which the essential oil showed moderate inhibitory activity against acetylcholinesterase (I%: 70.2%) and lipoxygenase (I%: 72.5%). Thus, the findings may be helpful for identifying the medicinal and therapeutic uses of the essential oil from the Magnolia genus.
