Sinteza fluoroforov s 4-fenilazo-anilinskim skeletom

Gabrovšek, Marko (avtor), Košmrlj, Janez (mentor)

Na podlagi molekulskih sond, ki so kazale ugodne optične lastnosti za uporabo v fluorescenčni mikroskopiji in vezavne lastnosti na odlage proteina tau, je bila zasnovana spojina 4-(4-((4-(etil(2-fluoroetil)amino)fenil)diazenil)fenil)-6-metil-2-okso-2H-piran-3-karbonitril. Na podlagi literaturnih podatkov tvorb gradnikov molekule je bila začrtana sintezna pot. Ta je vključevala reakcije Claisenove kondenzacije, diazotiranja, spajanja v azo spojino, fluoriranja in Knoevelagel-ove kondenzacije. V tem delu so predstavljene sinteze spojin, ki bi lahko služile kot intermediate na poti do željene spojine. Sinteza končne spojine pod izbranimi pogoji ni bila uspešna.

• Jezik: Slovenski jezik
• Ključne besede: fluorofori, azo spojine, Claisenova kondenzacija, sinteza
• Vrsta gradiva: Diplomsko delo/naloga
• Tipologija: 2.11 - Diplomsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2019
• PID: 20.500.12556/RUL-110547
• COBISS.SI-ID: 1538434755
• Datum objave v RUL: 16.09.2019

Sekundarni jezik

• Jezik: Angleški jezik

Izvleček

Based on molecular probes, that have favourable optical properties for use in fluorescence microscopy and favourable binding affinity towards protein tau aggregates 4-(4-((4-(ethyl(2-fluoroethyl)amino)phenyl)diazenyl)phenyl)-6-methyl-2-oxo-2H-pyran-3-carbonitrile was designed. Synthesis plan was chosen in accordance with literature data on the synthesis of building blocks present in the designed molecule. It included reactions of Cleisen condensation, diazotation, azo coupling, fluorination and Knoevelagel condensation. In this work, syntheses of intermediary compounds used for to obtain the final molecule are presented. The synthesis of the final compound was unsuccessful under the chosen conditions.

• Ključne besede: fluorophores, azo compounds, Cleisen condensation, synthesis