RP-HPLC determination of lipophilicity in series of quinoline derivatives

Abstract

Abstract:In the present paper we describe results on the synthesis and lipophilicity determination of a series of biologically active compounds based on their heterocyclic structure. For synthesis of styrylquinoline-based compounds we applied microwave irradiation and solid phase techniques. The correlation between RP-HPLC retention parameter log k (the logarithm of retention factor k) and log P data calculated in various ways is discussed, as well as, the relationships between the lipophilicity and the chemical structure of the studied compounds.© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

Ring-substituted 8-hydroxyquinoline-2-carboxanilides as potential antimycobacterial agents

“…[9][10][11]35,36,43 This is probably caused by the fact that between the hydroxyl moiety in C (8) of the quinoline nucleus and nitrogen of quinoline intramolecular H-bond affecting lipophilicity, solubility and basicity/acidity is formed. 44 Based on the presented results, it can be stated that log k values specify lipophilicity within individual series of the studied compounds better than log P values.…”

Preparation and Hydro-Lipophilic Properties of Selected Novel Chlorinated and Brominated N-Arylcinnamamides

“…Regarding these observations, it should be noted that the programs cannot always exactly calculate the lipophilicity contribution of substituents in ortho positions, e.g., in this case due to spatially close carboxamide linker [10,12,16,[18][19][20] (see compounds 7/2 or 4/6 when evaluated 2-Br-4-Cl (7) was less lipophilic than 2,4-Cl (2) and, to the contrary, disubstituted 3-Cl-4-Br (6) was more lipophilic than trisubstituted 2,4,5-Cl (4)). These facts are caused by intramolecular interactions that can be observed just for ortho substituents/substitutions [10,12,16,[18][19][20]21].…”

“…Therefore, reversed-phase high performance liquid chromatography (RP-HPLC) methods have become popular and widely used for lipophilicity measurement. A general procedure is the measurement of directly accessible retention time under isocratic conditions with varying amounts of an organic modifier in the mobile phase using end-capped non-polar C18 stationary RP columns and calculating the capacity factor k [4][5][6][7][8][9]. Log k, calculated from the capacity factor k, is used as the lipophilicity index converted to log P scale [4].…”

Chromatographic and Computational Study of Hydro-lipophilic Properties of <em>N</em>-Alkoxyphenylhydroxy-naphthalenecarboxamides

“…Since it was found that the lipophilicity of these significantly biologically effective agents determined their activity, in this study hydrolipophilic properties of all three series are investigated. Thus this contribution is a follow-up work to the previous papers [5][6][7][8][15][16][17][18][19][20][21][22][23][24][25] aimed at the physicochemical properties of new biologically active agents.…”

“…Therefore, reversed-phase high performance liquid chromatography (RP-HPLC) methods have become popular and widely used for lipophilicity measurement. A general procedure is the measurement of directly accessible retention time under isocratic conditions with varying amounts of an organic modifier in the mobile phase using end-capped non-polar C 18 stationary RP columns and calculating the capacity factor k [4][5][6][7][8]. Log k, calculated from the capacity factor k, is used as the lipophilicity index converted to log P scale [4].…”