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Synthesis and RP HPLC studies of biologically active semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones.

Pitucha M, Matysiak J, Senczyna B - Monatsh. Chem. (2012)

Bottom Line: The compounds showed regular retention behaviour in three chromatographic systems; their log k values decreased linearly with the increasing concentration of an organic modifier in the mobile phase.Differences between log k w values 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 log k w parameters obtained by RP-8 or RP-18 and determined by the computational approach log P were found.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Lublin, Lublin, Poland.

ABSTRACT

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, (1)H NMR and (13)C NMR spectroscopy. The compounds showed regular retention behaviour in three chromatographic systems; their log k values decreased linearly with the increasing concentration of an organic modifier in the mobile phase. The ratio of the intercept (log k w) to the slope of compounds is constant and the same for both groups of compounds on C18 and IAM stationary phases. Differences between log k w values 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 log k w parameters obtained by RP-8 or RP-18 and determined by the computational approach log P were found.

No MeSH data available.


Chromatograms of compound 12a obtained by IAM chromatography for different water contents in water/ACN mobile phase
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Fig2: Chromatograms of compound 12a obtained by IAM chromatography for different water contents in water/ACN mobile phase

Mentions: The log k values of compounds were determined using C-8, C-18 and IAM stationary phases. The mobile phases consisted of buffer mixed with various amounts of methanol or acetonitrile to give pH 7.4. Linear relationships were obtained between the log k and φ in the mobile phase in the whole studied ranges for all stationary phases. Generally, for semicarbazide derivatives and IAM chromatography, a larger content of water in the mobile phase can be used (Tables 1, 2). For some compounds log kw values on IAM were determined experimentally. The chromatograms of compound 12a are shown in Fig. 2.Table 1


Synthesis and RP HPLC studies of biologically active semicarbazides and their cyclic analogues 1,2,4-triazol-3-ones.

Pitucha M, Matysiak J, Senczyna B - Monatsh. Chem. (2012)

Chromatograms of compound 12a obtained by IAM chromatography for different water contents in water/ACN mobile phase
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495053&req=5

Fig2: Chromatograms of compound 12a obtained by IAM chromatography for different water contents in water/ACN mobile phase
Mentions: The log k values of compounds were determined using C-8, C-18 and IAM stationary phases. The mobile phases consisted of buffer mixed with various amounts of methanol or acetonitrile to give pH 7.4. Linear relationships were obtained between the log k and φ in the mobile phase in the whole studied ranges for all stationary phases. Generally, for semicarbazide derivatives and IAM chromatography, a larger content of water in the mobile phase can be used (Tables 1, 2). For some compounds log kw values on IAM were determined experimentally. The chromatograms of compound 12a are shown in Fig. 2.Table 1

Bottom Line: The compounds showed regular retention behaviour in three chromatographic systems; their log k values decreased linearly with the increasing concentration of an organic modifier in the mobile phase.Differences between log k w values 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 log k w parameters obtained by RP-8 or RP-18 and determined by the computational approach log P were found.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Lublin, Lublin, Poland.

ABSTRACT

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, (1)H NMR and (13)C NMR spectroscopy. The compounds showed regular retention behaviour in three chromatographic systems; their log k values decreased linearly with the increasing concentration of an organic modifier in the mobile phase. The ratio of the intercept (log k w) to the slope of compounds is constant and the same for both groups of compounds on C18 and IAM stationary phases. Differences between log k w values 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 log k w parameters obtained by RP-8 or RP-18 and determined by the computational approach log P were found.

No MeSH data available.