Lipophilicity as a Central Component of Drug-Like Properties of Chalchones and Flavonoid Derivatives

Abstract

Lipophilcity is an important physico-chemical parameter that influences membrane transport and binding ability to action. Migration distance following complete elution of compounds was used to calculate different lipophilicity-related parameters. The aim of this study is to show that lipophilicity is a central component of thiazole chalcones and flavonoid derivatives regarding their drug-like properties. Experimental and computational methods were used. This study considers 44 previously synthesized compounds (thiazole chalcones, flavanones, flavones, 3-hydroxyflavones, and their acetylated derivatives). The concerned compounds have shown antitumoral hallmarks and antibacterial activity in vitro. The experimental method used to determine compounds’ lipophilicity was the reverse-phase thin layer chromatography (RP-TLC). Lipophilicity related parameters—isocratic retention factor (RM), relative lipophily (RM0), slope (b), chromatographic hydrophobic index (φ0), scores of principal components (PC1/RM)—were determined based on reverse-phase chromatography results.

Comparison of the Utility of RP-TLC Technique and Different Computational Methods to Assess the Lipophilicity of Selected Antiparasitic, Antihypertensive, and Anti-inflammatory Drugs

“…The main reason for this fact can be, for example, the different adsorbing properties of applied stationary phases or eluents such as their elution strength or surface tension, which show an influence on the results of the R M parameter. As was confirmed in previous studies, the pH value of distilled water used as a mobile phase component also has a large impact on the value of both the chromatographic lipophilicity parameters and the experimental partition coefficients [8,11,18,31].…”

“…Many various lipophilicity descriptors and methods have been well described and proposed for the evaluation of the lipophilic properties of different compounds in review articles from recent years [7,8,9]. Currently, the chromatographic approach is used the most [10,11,12,13,14,15,16,17,18].…”

In silicoinvestigation of spice molecules as potent inhibitor of SARS-CoV-2

“…Lipophilicity or fat friendliness of a molecule defines the dissolving capability in fat, oil or any non-polar solvent (Lindsley, 2010 ). The water n -octanol partition coefficient (log Po/w) is used as the measure of lipophilicity (Constantinescu et al., 2019 ). Various computational methods are developed for the estimation of log Po/w for diverse performance upon different chemical sets.…”

Synthesis of Degraded Limonoid Analogs as New Antibacterial Scaffolds against Staphylococcus aureus

“…Some authors suggest that lipophilicity is one of the most important molecular properties to be considered on decision-making in medicinal chemistry [ 19 ], and certain studies pointed out that high hydrophilicity decreases the biological activity of certain natural products and, as a consequence, higher lipophilicity, a higher activity [ 12 ]. Lipophilicity is represented by the descriptors partition coefficient (log P)—which is often used in the analysis of structure-activity relationships (SAR and QSAR) [ 49 , 50 , 51 , 52 ]—and distribution coefficient (log D) that is considered as the most impactful parameter by some authors, rather than log P [ 52 ].…”