Sinteza fluoroforov s 4-feniletinil-fenilaminskim skeletom

Žnideršič, Nika (author), Gazvoda, Martin (mentor)

Cilj diplomske naloge je bila sinteza novih fluoroforov s 4-feniletinil-fenilaminskim skeletom, ki bi bili na podlagi svojih optičnih in vezavnih lastnosti primerni za detekcijo proteina tau in vitro kot tudi in vivo. Sinteza 4-(4-((4-(etil(2-fluoroetil)amino)fenil)etinil)fenil)-6-metil-2-okso-2H-piran-3-karbonitril je vključevala reakcijo Claisenove kondenzacije, pripajanje po Sonagashiri in fluoriranje. Uspešno je bil sintetiziran diketon 1-(4-((4-(etil(2-hidroksietil)amino)fenil)etinil)fenil)butan-1,3-dion, ki lahko služi kot izhodna spojina za pripravo želene končne spojine.

• Language: Slovenian
• Keywords: molekulska sonda, organska sinteza, reakcija pripajanja, fluoriranje
• 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-109940
• COBISS.SI-ID: 1538425283
• Publication date in RUL: 10.09.2019

Secondary language

• Language: English
• Title: Synthesis of fluorofores with 4-phenylethynyl-phenylamine skeleton

Abstract

The goal of this thesis was to synthesize new fluorophores with 4-phenylethynyl-phenylamine scaffold that would be suitable for detection of tau protein in vitro as well as in vivo, based on their optical and binding properties. Synthesis of 4-(4-((4-(ethyl(2-fluoroethyl)amino)fenyl)ethynyl)fenyl)-6-methyl-2-oxo-2H-pyran-3-carbonitrile included Claisen condensation, Sonagashira coupling and fluorination reaction. Diketone 1-(4-((4(ethyl(2-hydroxyethyl)amino)¬phenyl)ethynyl)¬phenyl)¬butane-1,3-dione was successfully synthesized and can serve as a starting compound for the synthesis of the desired compound.

• Keywords: molecular probe, organic synthesis, coupling reaction, fluorination reaction