Sinteza fluoroforov s 4-fenilazo-anilinskim skeletom

Gabrovšek, Marko (author), 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.

• Language: Slovenian
• Keywords: fluorofori, azo spojine, Claisenova kondenzacija, sinteza
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2019
• PID: 20.500.12556/RUL-110547
• COBISS.SI-ID: 1538434755
• Publication date in RUL: 16.09.2019

Secondary language

• Language: English

Abstract

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.

• Keywords: fluorophores, azo compounds, Cleisen condensation, synthesis