Determination of the lipophilicity of some new thiosemicarbaside derivatives by reversed-phase thin-layer chromatography

Abstract

Summary. In this study, the chromatographic behavior of a newly synthesized series of 1,4-disubstituted thiosemicarbazide derivatives and products of their dehydrocyclization is presented. These compounds have been subjected to this study because they exhibit antimicrobial activity. The compounds have been chromatographed on RP-18 and on cyano-bonded silica chromatographic phases with eluents containing water and an organic modifier (methanol, dioxane, acetone, acetonitrile or tetrahydrofuran) of various concentrations. Statistically proved linear relationships between the retention parameter (R M ) and the concentration of organic modifier in the mobile phase allow the extrapolation procedure to obtain R ) were compared with the log P values calculated by use of four different software packages. The values of the correlation coefficients of these relationships are higher for the cyanopropyl phase than for RP-18. Moreover, in this work the influences of different mobile phase modifiers and adsorbent layers on experimentally obtained lipophilicity parameters were analyzed and compared. Generally, the best correlations were obtained for systems with the cyanopropyl-bonded stationary phase in comparison with RP-18.

Thin-Layer Chromatography on Reversed Phase in the Characterization of Retention Behaviour, Lipophilicity, and Pharmacokinetics of Cyanoacetamide Derivatives

“…31,32 Also, for getting information about lipophilicity and bioproperties of molecules in Quantitative Structure-Retention Relationship (QSRR) model, the values of chromatographic retention parameter, RM 0 , obtained by RP-TLC are widely used. [33][34][35][36][37] Thin layer chromatography on reversed phase has proved to be a suitable method between various chromatographic methods, thanks to its simplicity, price, using small amounts of the substance, accuracy, repeatability and efficiency, as well as the possibility of differentiating of lipophilicity between structurally similar molecules. 38 The evaluation of a molecule as a potential therapeutic agent may be further improved by introducing the Lipinski's rule of five.…”

Quantitative structure-retention relationship study of oxothiazolidines using multivariate analysis

“…Cijano-modifikovani silika-gel se pokazao kao veoma dobar sorbent kod određivanja parametara lipofilnosti [40][41][42][43][44] . Mogućnost korišćenja CN-stacionarne faze pri određivanju parametra lipofilnosti može se pripisati sličnošću sa fosfolipidnom ćelijskom membranom.…”