Sinteza derivata 1,2-difeniletina s podaljšano konjugacijo

Klander, Daša (author), Košmrlj, Janez (mentor)

Za namen detekcije depozitov prekomerno fosforiliranih proteinov tau in posledično zgodnjo detekcijo Alzheimerjeve bolezni je bilo razvitih že mnogo molekulskih sond. Te molekulske sonde morajo imeti ugodne vezavne in optične lastnosti. V tej diplomski nalogi smo z uporabo Sonogashirove reakcije brez uporabe bakra in amina sintetizirali dve novi molekulski sondi, 4-((4-(dimetilamino)fenil)etinil)benzonitril in 4-((4-(etil(2-hidroksetil)amino)fenil)etinil)benzonitril. Ta dva derivata 1,2-difeniletina smo pripravili iz bromobenzonitrila in ustreznega acetilna v prisotnosti katalizatorja Pd-bis(Py-tzNHC). En produkt smo izolirali z avtomatsko kolonsko kromatografijo na PuriFlashu, drugega pa s preparativno kolonsko kromatografijo na SiO2. Produkta smo nato okarakterizirali s tehniko HRMS-ESI, posneli 1H NMR, 13C NMR, IR spektre, izmerili temperaturo tališča in s HPLC tehniko preverili čistost produktov.

• Language: Slovenian
• Keywords: Alzheimerjeva bolezen, molekulska sonda, sinteza, spajanje po Sonogashiri
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2021
• PID: 20.500.12556/RUL-129833
• COBISS.SI-ID: 80108291
• Publication date in RUL: 08.09.2021

Secondary language

• Language: English
• Title: The synthesis of 1,2-diphenylethyne derivate with an extended conjugation

Abstract

Several molecular probes have been designed with intention to detect hyperphosphorylated tau proteins deposits and with that earlier detection of Alzheimer disease. These molecular probes need to have good binding and optical properties. In this Bachelor's thesis, two new molecular probes have been synthesised, 4-((4-(dimethylamino)phenyl)ethynyl)benzonitrile and 4-((4-(ethyl(2-hydroxyethyl)amino)phenyl)ethynyl)benzonitrile, by using copper-free and amino-free Sonogashira coupling reaction. These two 1,2-diphenylethyne derivates have been prepared using bromobenzonitrile and the appropriate acetylene in the presence of a Pd-bis(Py-tzNHC) catalyst. One product was isolated by automatic column chromatography on PuriFlash and the other one by silica gel column chromatography. The products were then characterized by HRMS-ESI, 1H NMR, 13C NMR and IR spectroscopy, their melting points were measured and by using the HPLC their purity was determined.

• Keywords: Alzheimer disease, molecular probes, synthesis, Sonogashira coupling