Coumarin-based compounds containing a chalcone moiety exhibit antimicrobial activity. These substances are potential drugs and it is important to determine their pKa values. However, they are almost insoluble in water. The dissociation constant was experimentally determined by potentiometric titration for 3-[3-(2-nitrophenyl)prop-2-enoyl]-2H-1-benzopyran-2-one because this compound shows good activity and solubility. A number of different computer programs for the calculation of the dissociation constant of chemical compounds have been developed. The pKa value of the target compound was calculated using three different computer programs, i.e., the ACD/pKa, CSpKaPredictor and ADME/ToxWEB programs, which are based on different theoretical approaches. The analysis demonstrated good agreement between the experimentally observed pKa value of 3-[3-(2-nitrophenyl)prop-2-enoyl]-2H-1-benzopyran- 2-one and the value calculated using the computer program CSpKa.
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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