Oxidative stress is directly related to several diseases and symptoms, where antioxidant compounds, such as xanthenes, may become important in prevention and/or treatmant. Ten biologically active 9-aryl substituted 2, 6, 7-trihydroxyxanthen-3-one derivatives were synthesized using reliable one-pot synthesis and their structures were confirmed by IR, 1H and 13C NMR spectroscopy and mass spectrometry. Some of the synthesized compounds were scanned for their antioxidant potency using electrochemical method cyclic voltammetry of immobilized microparticles. Substitution of hydrogen at the phenyl ring of 2, 6, 7-trihydroxy-9-phenylxanthen-3-one with an electron-donating group affected the reducing power of the compounds by lowering the biological oxidation potential. These results signify the importance of xanthen-3-one derivatives as antioxidant agents and their further biological evaluation.
For some synthesized coumarin derivatives, 1H and 13C NMR isotropic chemical shifts and some other molecular properties were calculated using density functional theory. The calculations yield reliable results, that are in good correlation with experimental data. This is a good basis for the collaboration between experimentalists and quantum chemists.
Ten biologically active derivatives of 2,6,7-trihydroxyxanthen-3-one, previously synthesized and characterised, were investi - gated for their in vitro antimicrobial and antiproliferative activity. Compounds were tested on three bacteria, Staphylococcus aureus , Bacillus subtilis and Escherichia coli , and two fungi strains, Candida albicans , and Saccharomyces cerevisiae . The best activity against E. coli showed non-substituted compound 1 . The most potent against fungi strains was compound 7 with ortho methoxy substituent. Compound 4 exerted the most potent antiproliferative activity in the micromolar range (0.1–10 µM) on tested tumour cell lines except on SW620. Additional Western blot analyses showed increased cyclin B1 levels in HeLa cells treated with compound 4 , which is a major mitotic catastrophe’s marker and decreased levels of Wee1 and Erk ½ kinases involved in regulation of the mitotic process. The most potent compounds after in vitro tests were subjected to molecular docking simulations to evaluate enzyme binding affinity, and provide further evidence for experimentally observed biological effects in vitro .
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