title: Synthesis and RP HPLC studies of biologically active semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones.
abstract: The retention behaviour of semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones, has been investigated by RP-8, RP-18 and IAM HPLC. The structures of new derivatives were proved by elemental analyses, IR,1H NMR and13C NMR spectroscopy. The compounds showed regular retention behaviour in three chromatographic systems; their logkvalues decreased linearly with the increasing concentration of an organic modifier in the mobile phase. The ratio of the intercept (logkw) to the slope of compounds is constant and the same for both groups of compounds on C18 and IAM stationary phases. Differences between logkwvalues from the octadecyl stationary phase of corresponding cyclic and linear derivatives are constant, and they are related to the mechanism of synthesis of 1,2,4-triazol-3-ones from linear substrate semicarbazides, which was confirmed by modelling studies. Good correlations between logkwparameters obtained by RP-8 or RP-18 and determined by the computational approach logPwere found.
authors.affiliation: Department of Organic Chemistry, Medical University of Lublin, Lublin, Poland.
authors.forename: Monika
authors.initials: M
authors.lastname: Pitucha
authors.affiliation: Department of Chemistry, University of Life Sciences in Lublin, Lublin, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Matysiak
authors.affiliation: Department of Chemistry, University of Life Sciences in Lublin, Lublin, Poland.
authors.forename: Bogdan
authors.initials: B
authors.lastname: Senczyna
keywords: 1,2,4-Triazol-3-one; IAM chromatography; Lipophilicity; RP HPLC; Semicarbazide