Determination of lipophilicity of α‐(4‐phenylpiperazine) derivatives of N‐benzylamides using chromatographic and computational methods

Abstract

This paper describes the evaluation of lipophilicity of alpha-(4-phenylpiperazine) derivatives of N-benzylamides. We employed reversed-phase thin-layer chromatography (RP-TLC) and reversed-phase high performance liquid chromatography (RP-HPLC) as experimental methods, using mixtures of acetonitrile and water as the mobile phases with addition of 0.1%TFA in the HPLC experiments. Retention parameters (R(M)) and capacity factors (log k) determined by applying these methods were linearly dependent on the acetonitrile concentration and enabled us to estimate the relative lipophilicity factors: R(M0) and log k(0). These factors were compared with the calculated partition coefficients C log P obtained using several software packages. The results indicate that both experimental methods (RP-TLC and RP-HPLC) yielded similar results, and these methods enable determining the lipophilicity of alpha-(4-phenylpiperazine) derivatives of N-benzylamides. Significant correlations were found between log P values calculated by Pallas, ALOGPS and C log P Chem3D programs and the experimental data.

Application of a Library of Artificial Receptors Formed by Self‐Organization of N‐Lipidated Peptides Immobilized on Cellulose for Preliminary Studies of Binding of N‐Phenylpiperazines

“…Parameters of relative lipophilicity of this set of compounds have been determined using chromatographic and computational methods [39]. The obtained results indicated significant correlations between chromatographic methods and log P calc values calculated by Pallas program.…”

Application of a Library of Artificial Receptors Formed by the Self-Organization of N-Lipidated Peptides Immobilized on Cellulose in Studying the Effects of the Incorporation of a Fluorine Atom

“…In the previous study, the parameters of the relative lipophilicity of this set of compounds were determined using chromatographic and computational methods . It was found that in all the cases the presence of a fluorine atom in the phenyl ring increased the lipophilicity of compounds 5 , 7 , and 9 in comparison to parent compounds 4 , 6 , and 8 ; however, the increase was relatively small.…”

Zastosowanie TLC w układzie faz odwróconych oraz metod obliczeniowych do wyznaczenia lipofilowości eplerenonu

“…posłużył do oceny lipofilowości, a następnie aktywności biologicznej wielu nowo zsyntezowanych związków organicznych [2][3][4][5][6]. W praktyce, w celu dokonania krytycznej oceny uzyskanych wyników, często dokonuje się porównania danych doświadczalnych otrzymanych różnymi technikami, w tym chromatograficznymi, z wartościami współczynnika podziału (logP) wyznaczonymi teoretycznie, tj.…”