Lipophilicity is one of the important properties of bioactive molecules, according to which the nature of a potential drug is assessed. Evaluation of the lipophilicity of selected cinnamic acid derivatives was performed by high-performance liquid chromatography (HPLC) using reversed (RP) stationary phase C18 and under isocratic conditions. In the case of determining the capacity factor k, methanol and water were applied to the system as the mobile phase. The distribution coefficient D was determined using a mobile phase composed of methanol and acetate buffer (pH 7.4 or pH 6.5) to ensure a constant pH. This contribution aims to compare the influence of various factors on the lipophilicity of selected trifluoromethyl substituted cinnamanilides, including pH and the position and nature of specific substituents in the anilide portions of the molecules. The results of this study will then be used to evaluate structure-lipophilicity relationships, druglikeness, and structure-activity relationships.

Acknowledgement: This study was supported by a grant project of the Comenius University in Bratislava, Slovakia (UK/228/2021) and by the Slovak Research and Development Agency (APVV-17-0373).