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Synthesis of novel fluorinated tetrazines for selective cell labeling via metal-free "click" reactions
 Výbošťoková, Júlia ; Sedláček, Ondřej (advisor) ; Baszczyňski, Ondřej (referee)
This diploma thesis deals with the synthesis and characterization of novel phenyltetrazine fluorinated compounds that contain a fluorinated substituent in the ortho, meta or para position with respect to the tetrazine group. These compounds are used in bioorthogonal cell labeling through so-called "click" reactions. Change in the chemical shift of the fluorinated substituent signal in 19 F NMR after the "click" reaction will allow in vitro/in vivo monitoring of labeling using 19 F MRI. For this reason, the spatial proximity of the fluorinated substituent to the tetrazine part of the molecule is important in terms of real-time detection of the "click" reaction itself. In the beginning, commercially unavailable aromatic nitriles were synthesized. In the next step, tetrazine synthesis was performed from synthesized and commercially available starting nitriles by "Pinner-like" reaction. This involved a reaction with acetonitrile or (3,3,3)-trifluoropropionitrile and hydrazine monohydrate in the presence of Lewis acid Zn(OTf)2. Reactions with ortho-substituted phenyltetrazines did not yield any positive results. Conversely, the synthesis of meta and para-substituted phenyltetrazines was successful. All successfully synthesized tetrazines undergo IEDDA "click" reactions with trans-cyclooctenol. Keywords:...
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