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The mangosteen peels contain biologically active compounds, with antioxidant and anticancer properties. Among these isolated phytochemicals, α-mangostin is one of the most powerful natural antioxidants and anticancer compounds. This study focused on synthesizing novel α-mangostin (α-MG) derivatives at positions of C-3 and C-6 from extracted α-MG of mangosteen peels and investigating antioxidant and anticancer activities. The structures of the synthesized compounds were determined by using MS, 1H-NMR, 13C-NMR, and HPLC. The analysis of the interaction between structure and bioactivity showed that phenol groups on C-3 and C-6 positions play a crucial role in antiproliferative activity to boost both anticancer efficacy and drug-like properties. The antioxidant activity of α-MG and its derivatives were investigated by the DPPH method. Among α-MG derivatives, 1-hydroxy-7-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-9-oxo-9H-xanthene-3,6-diyl bis(2-bromobenzoate) (compound 4) exhibited significant antioxidant property. The in vitro cytotoxicity against various cancer cell lines (HeLa, MCF-7, NCI–H460, and HepG2) was evaluated by the standard sulforhodamine B assay. The anticancer activities (HeLa, MCF-7, NCI–H460, and HepG2) of compound 4 are five to six times higher than those of α-MG and other derivatives. The acetylation at C-3 and C-6 of α-MG by halogen of benzoyl greatly improved cancer cell toxicity. Our results provide new opportunities for further explorations of α-MG derivatives for antioxidant property and promise as drugs in cancer therapy.

Propranolol is one of the first medications of the beta-blocker used for antihypertensive drugs. This study reports the facile route for the synthesis of propranolol and its novel derivatives. Herein, propranolol synthesis proceeded from 1-naphthol and isopropylamine under mild and less toxic conditions. Novel propranolol derivatives were designed by reactions of propranolol with benzoyl chloride, pyridinium chlorochromate, and n-butyl bromide through esterification, oxidation reduction, and alkylation, respectively. The isolation and purity of compounds were conducted using column chromatography and thin-layer chromatography. Mass spectrometry and 1H-NMR spectroscopy were applied to identify new compounds structure. Propranolol derivatives from 2-chlorobenzoyl chloride (compound 3), 2-fluorobenzoyl chloride (compound 5), and especially acetic anhydride (compound 6) manifested high yields and significantly increased water solubility. Six semisynthetic propranolol derivatives promise to improve antioxidative and biological activities.