In this thesis, we are describing a preparation of new smart molecular probes which could be used for an early detection of the Alzheimer’s disease. Compounds were designed based on the “push-pull” architecture – this is a π-system on one side end-capped with an electron-donating group and on the other side with the electron-accepting group (D–π–A). To allow for a fast and straight-forward diversification of the electron-donating part of the molecule, we were also working on developing optimized reaction conditions for a palladium catalysed late-stage C-N coupling. With methodical screening of the reaction conditions on a model reaction between 8 and pyrrolidine, we have shown that amination in the last step is possible despite presence of 4-methyl-2-oxo-2H-pyran-3-carbonitrile group and have also demonstrated this transformation using dimethylamine as an amine source. We have characterized synthesized compounds with a 1H and 13C NMR and IR spectroscopy, high-resolution mass spectrometry, recorded their melting point and determined their purity with HPLC analysis. For chosen compounds, we have also recorded their optical properties and determined their absorption, emission and excitation maximums. For those compounds we have also calculated their molar absorptivity and quantum yields. Partners on the project have also performed preliminary in vitro and ex vivo biological tests using selected compounds, which gave very promising results.
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