This review focuses on the synthesis and biological activity of flavones and their related flavonoidic compounds, namely flavonols and aurones. Among the biological activities of natural and synthetic flavones and aurones, their anticancer, antioxidant, and antimicrobial properties are highlighted and detailed in this review. Starting from the structures of natural flavones acting on multiple anticancer targets (myricetin, genkwanin, and other structurally related compounds), new flavone analogs were recently designed and evaluated for their anticancer activity. The most representative compounds and their anticancer activity are summarized in this review. Natural flavones recognized for their antimicrobial properties (baicalein, luteolin, quercetol, apigenin, kaempferol, tricin) have been recently derivatized or structurally modulated by chemical synthetic methods in order to obtain new effective antimicrobial flavonoidic derivatives with improved biological properties. The most promising antimicrobial agents are systematically highlighted in this review. The most applied method for the synthesis of flavones and aurones is based on the oxidative cyclization of o-hydroxychalcones. Depending on the reaction conditions and the structure of the precursor, in some cases, several cyclization products result simultaneously: flavones, flavanones, flavonols, and aurones. Based on the literature data and the results obtained by our research group, our aim is to highlight the most promising methods for the synthesis of flavones, as well as the synthetic routes for the other structurally related cyclization products, such as hydroxyflavones and aurones, while considering that, in practice, it is difficult to predict which is the main or exclusive cyclization product of o-hydroxychalcones under certain reaction conditions.

This review focuses on the synthesis and biological activity of flavones and their related flavonoidic compounds: flavonols and aurones. Among the biological activities of flavones and aurones, the anticancer, antioxidant and antimicrobial properties are highlighted and detailed in this review. The most applied method for the synthesis of flavones and aurones is based on the oxidative cyclisation of o-hydroxychalcones. Depending on the reaction conditions and the structure of the precursor, in some cases several cyclization products result simultaneously: flavones, flavanones, flavonols and aurones. Based on the literature data and the results obtained in our research group, our aim is to highlight the most promising methods for the synthesis of flavones, as well as the synthetic routes for the other structurally related cyclization products, hydroxyflavones and aurones, considering that in practice it is difficult to predict which is the main or exclusive cyclisation product of o-hydroxychalcones under certain reaction conditions.

Lipophilicity, a significant physicochemical parameter of bioactive molecules, along with absorption, distribution, metabolism, excretion parameters and toxicity risk, was investigated for 32 thiazolo[3,2-b][1,2,4]triazole and imidazo[2,1-b][1,3,4]thiadiazole derivatives with anti-inflammatory potential. The experimental lipophilicity study was carried out by reversed-phase thin-layer chromatography in a binary isopropanol-water mobile phase, and the obtained results were compared with the theoretical lipophilicity parameters estimated by various computational methods. Strong correlations were found between the experimental retention factors and calculated partition coefficients. A modified Petra/Osiris/Molinspiration analysis was performed on the previously synthesized compounds, using SwissADME, Osiris and Molinspiration web tools. The predicted in silico parameters highlighted the most promising compounds as potential drug candidates. The compounds showed good gastrointestinal absorption, moderate activity according to the bioactivity score (values situated between −1.25 and −0.06), and a safe toxicity profile. The results obtained in this study will contribute to lipophilicity studies and other future studies focused on modulating new drug candidates starting from thiazolo[3,2-b][1,2,4]triazole and imidazo[2,1-b][1,3,4]thiadiazole derivatives, which are important heterocycles in medicinal chemistry.

The retention behavior for a series of new polyheterocyclic compounds containing azolic rings (1,3-thiazole, 1,2,4-triazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole) has been investigated using reversed-phase thin-layer chromatography. Different approaches and computational methods were employed to evaluate their lipophilicity indices derived from chromatographic parameters. The obtained experimental results were correlated with various lipophilicity indices estimated via different computer software and internet websites. A strong correlation between experimental and computed results was observed. Furthermore, the lipophilicity parameters obtained by applying principal component analysis divided the investigated compounds into four groups according to their structural similarities.