Effect of electron acceptor groups on partition coefficient of phenothiazine derivatives at the water / 1,2-dichloroethane interface

L.M.A. MONZÓN; L.M. YUDI

JOURNAL OF ELECTROANALYTICAL CHEMISTRY

Elsevier

Lugar: Lausanne - Suiza; Año: 2006 vol. 591 p. 46 - 52

0022-0728

The transfer of phenothiazine derivatives (promazine, chlorpromazine, triflupromazine, methotrimeprazine, perphenazine and fluphenazine) across the waterj1,2-dichloroethane interface was studied using cyclic voltammetry. The partition coefficients of ionic species of phenothiazines, logPXH , were calculated from the transfer potentials measured at pH < pKa. These values were related with the Hammet parameter of substituents in order to find a dependence with the presence of electron acceptor substituents in the molecule. These electron acceptor groups affect the biological activity of these drugs. The results indicated that log PXHþ can be used in structure–activity correlations as it takes into account the effects of substituents on the main positions within the phenothiazine molecule. j1,2-dichloroethane interface was studied using cyclic voltammetry. The partition coefficients of ionic species of phenothiazines, logPXH , were calculated from the transfer potentials measured at pH < pKa. These values were related with the Hammet parameter of substituents in order to find a dependence with the presence of electron acceptor substituents in the molecule. These electron acceptor groups affect the biological activity of these drugs. The results indicated that log PXHþ can be used in structure–activity correlations as it takes into account the effects of substituents on the main positions within the phenothiazine molecule. Keywords: ITIES; Ion transfer; Lipophilicity; Phenothiazines; Drugs behavior