Abstract
Lipophilicity of twelve synthesized chalcones, whose ring B is a ortho, meta or para monosubstituted with alkyl, oxyalkyl groups or halogens was determined by reverse phase liquid chromatography, using octadecyl-functionalized (RP-18) silica gel as a stationary phase and two-component mixture of methanol/water as a mobile phase. Linear dependence of logk? values of the volume fraction of methanol in the mobile phase was determined for all analyzed compounds, with high coefficient of correlation (r > 0.99). Extrapolation of the line to 0% methanol concentration resulted in the capacity factor of chromatographic system where water is the mobile phase (logkw). For five standard substances, chemically similar to chalcones, logkw values were determined under experimental conditions and they were correlated with logP values of those compounds available in the literature. logPEXP values of synthesized chalcones were calculated on the basis of the created standard curve. In order to estimate the relevance of the experimentally obtained logP values for chalcones, correlation of logPEXP values with the logP values obtained through various computational procedures was performed using linear regression analysis. Statistical parameters of dependence showed that the best matching of the results had been achieved with ChemOffice program, suggesting that this program is suitable for calculating logP values of newly-synthesized chalcones, as well as of compounds structurally similar to chalcones.
Highlights
para monosubstituted with alkyl
halogens was determined by reverse phase liquid chromatography
values of the volume fraction of methanol in the mobile phase was determined for all analyzed compounds
Summary
Halkoni su prirodni proizvodi biljnog porekla, rasprostranjeni u voću, povrću, začinima i čajevima, a nastaju kao intermedijeri u sintezi flavonoida i flavanona koju katalizuje enzim halkon sintaza. Halkoni predstavljaju seco flavonoidne strukture kod kojih su dva aromatična prstena povezana preko α,β-nezasićenog ketonskog mosta. Halkoni imaju širok spektar bioloških aktivnosti: antiinflamatornu [1,2,3], antibakterijsku [1,2,4,5], fungicidnu [1,2], antiproliferativnu [1,2,6,7], tuberkulostatsku [1,8] i druge, ali i nisku selektivnost koja ograničava kliničku primenu ovih jedinjenja [1]. Mutagenog i antikancerogenog delovanja je poznat i ogleda se u vezivanju za nukleinske kiseline slično alkilirajućim agensima [1]
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
