Chrysin, a naturally occurring flavonoid, exhibits a broad spectrum of biological activities, including showing anticancer properties. However, its clinical application is limited by poor bioavailability and low solubility. The introduction of an amine, amide, ester, or alkoxy group to a flavone skeleton influences the biological activity. This review also discusses hybrid compounds, such as the chrysin–porphyrin hybrid, which are characterized by higher biological activity and better bioavailability properties than single molecules. This review concentrates on the anticancer activity of chrysin and its derivatives against the most popular cancers, such as breast, lung, prostate, and gastrointestinal tumors.

Anticancer drug design has been reformed by the creation of heterocyclic hybrids. The introduction of a quinoline scaffold affects the activity, toxicity, and bioavailability of new compounds. The aim of this study was to synthesize and evaluate the biological activity of hybrids of 1,4-naphthoquinone with the 8-hydroxyquinoline moiety. The structure of the new compounds was characterized using spectroscopic methods, such as HR-MS, NMR, and IR. The analysis was supplemented by calculated NMR and IR spectra. The physicochemical properties and bioavailability of the compounds were examined using in silico methods. An analysis of reactivity descriptors showed that the compounds are good electron acceptors and exhibit high reactivity. Bioavailability properties confirm that hybrids could be good oral administration drugs. The biological potential of hybrids was examined by designation of the enzymatic conversion rate of the NQO1 protein and in vitro against cancer cell lines with overexpression of the gene encoding the NQO1 protein. The possibility of interaction between the tested ligand and the NQO1 protein was examined by molecular docking methods.

Head and neck cancer (HNC) therapy is limited; therefore, new solutions are increasingly being sought among flavonoids, which exhibit numerous biological properties, including potential anticancer activity. However, because they are mostly insoluble in water, are unstable and have low bioavailability, they are subjected to chemical modification to obtain new derivatives with better properties. This study aimed to synthesize and analyze new propargyloxy derivatives of galangin, kaempferol and fisetin, and to evaluate their anticancer activity against selected HNC cell lines. The obtained derivatives were assessed by spectroscopic analysis; next, their anticancer activity was evaluated using a flow cytometer and real-time cell analysis. The results showed that only the fisetin derivative was suitable for further analysis, due to the lack of crystal formation of the compound. The fisetin derivative statistically significantly increases the number of cells in the G2/M phase (p < 0.05) and increases cyclin B1 levels. A statistically significant increase in the number of apoptotic cells after being exposed to the tested compound was also observed (p < 0.05). The data indicate that the obtained fisetin derivative exhibits anticancer activity by affecting the cell cycle and increasing apoptosis in selected HNC lines, which suggests its potential use as a new medicinal agent in the future.

Ziołolecznictwo stanowi jedną z głównych gałęzi tradycyjnej medycyny chińskiej (traditional Chinese medicine – TCM). W pracy skupiono się na aktywności biologicznej wybranych flawonoidów, a także konkretnych przykładach wpływu tych substancji na różne układy organizmu. Flawonoidy to grupa związków chemicznych zawartych w surowcach roślinnych, miodzie, propolisie czy grzybach stosowanych w TCM. Chryzyna, galangina, kemferol i fisetyna to przykłady flawonoidów wykazujących m.in. właściwości przeciwutleniające, przeciwzapalne czy przeciwbakteryjne. Właściwości te są przedmiotem wielu badań naukowych, mających na celu zbadanie ich potencjalnego działania terapeutycznego.

Quinoline and isoquinoline moieties occur in many natural and synthetic compounds exhibiting high biological activity. The purpose of this study was to analyze the chemical structures of 5,8-quinolinedione and 5,8-isoquinoline derivatives using FT-IR spectroscopy supplemented with theoretical DFT calculations. Spectroscopic measurements were conducted using the attenuated total reflection (ATR) mode in the frequency range of 4000–400 cm⁻¹. An analysis of FT-IR spectra was carried out, assigning the characteristic vibration frequencies of various functional groups to individual peaks. It was found that the experimental and calculated FT-IR spectra showed a good correlation for all the compounds under study. The most significant difference in the spectra occurred in the region of carbonyl bands. For compounds with the 5,8-quinolinedione moiety, two separated C=O vibration peaks were observed, while for compounds with the 5,8-isoquinolinedione moiety, the carbonyl vibrations created only one peak. This difference makes it possible to distinguish between the 5,8-quinolinedione and 5,8-isoquinolinedione derivatives.

The molecular structure of 3-diethoxyphosphoryl-28-[1-(1-deoxy-β-D-glucopyranosyl)-1H-1,2,3-triazol-4-yl]carbonylbetulin was investigated through various experimental and theoretical methods. X-ray diffraction, Hirshfeld surface, experimental and calculated FT-IR spectra analysis, molecular electrostatic potential (MEP) and molecular orbital (HOMO and LUMO) were used for the analyses. It was found that the introduction of a triazole substituent affects the arrangement of molecules in the crystal structure and the formation of hydrogen bonds. The Hirshfeld surface analysis shows that the red regions are concentrated near groups, which create hydrogen bonds, which means that the hydrogen bonds are strong. The analysis of HOMO and LUMO orbitals and the chemical reactivity descriptors shows that the compound is kinetically and chemically stable. A molecular electrostatic potential map was used to analyze the electrophilic and nucleophilic area in the molecule.