témavezető: Kurtán Tibor
társ-témavezető: Mándi Attila
helyszín (magyar oldal): Department of Organic Chemistry, University of Debrecen, Debrecen, Hungary, Chemistry Building helyszín rövidítés: E424
A kutatási téma leírása:
Elucidation of the absolute stereochemistry (configuration and conformation) is the final step in the structural elucidation of chiral drug molecules and pharmacologically active derivatives. The absolute configuration (AC) of optically active non-racemic stereoisomers can be determined by means of chiroptical methods (e.g. electronic and vibrational circular dichroism i.e. ECD and VCD or optical rotation i.e. OR) based on the interaction of the left and right circularly polarized components of the linearly polarized light with the sample. Since a significant portion of pharmacologically active derivatives is chiral and thus exists in the form of at least two stereoisomers, and these stereoisomers can exploit markedly different pharmacodynamic or pharmacokinetic behavior, knowledge of the AC and/or dominant conformation has profound importance in the case of newly isolated or synthesized potentially bioactive derivatives.
Depending on the structure of the studied molecule, chiroptical data obtained by different methods are often complementary and thus their combined application can establish a more reliable configurational assignment. Chiroptical techniques can be applied to elucidate relative configuration in special cases, but DFT calculation of NMR shift values or combined application of chiroptical and NMR methods are more appropriate to solve this kind of problem.
Stereoselective Knoevenagel-1,5-hydride shift-cyclization, Knoevenagel-hetero-Diels-Alder cascade reactions and alternative domino cyclization sequences of substituted furan, thiophene and other derivatives are carried out in our laboratory. In silico studies and understanding the mechanism of these reactions can help both to refine the synthetic procedures and design novel potent heterocycles.
The enantiomeric excesses of the synthetic or natural heterocycles investigated in our laboratories are to be analyzed by chiral HPLC coupled with electronic circular dichroism polarimeter and aided with ECD calculations.
előírt nyelvtudás: english további elvárások: basic stereochemical, spectroscopic, chromatography, Linux and programming knowledge, accuracy
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