Collect. Czech. Chem. Commun. 1992, 57, 1739-1746

Biologically Important Physicochemical Properties of Some Cephalosporins

Katarína Škvareninováa, Štefan Baláža, Ernest Šturdíka, Miroslav Veverkab, Jana Adamcováa and Jana Olexováa

a Department of Biochemical Technology, Slovak Technical University, 812 37 Bratislava
b Department of Inorganic Chemistry, Slovak Technical University, 812 37 Bratislava


In the series of cephalosporin derivatives, consisting of eight 7-(R1-CH2-CO-NH)cephalosporanic acids and of seven analogical compounds with 3-acetoxymethyl replaced by 3-CH3, physicochemical properties, which are expected to play a role in their antibacterial effects (the transport rate parameters and partition coefficients in the systems 1-octanol-water and 1-octanol-buffer, dissociation constants of the 4-carboxyl group, reactivity towards L-glutathione imitating the nucleophilic groups of the cell components and hydrolysis rate parameters), were determined. Linear dependences were observed between the partition coefficients and the π-constants of the varying substituents as well as between reactivity towards SH-groups of L-glutathione and OH-groups. The relationship between the transport rate parameters and partition coefficients, both measured in buffered as well as non-buffered system, was described by a common non-linear equation.