Sinteza možnih metabolnih produktov analoga FDDNP

Brodnik, Ana (avtor), Košmrlj, Janez (mentor)

2-(1-(4-((4-(Etil(2-(fluoro)etil)amino)fenil)etinil)fenil)etiliden)malononitril je zaradi ugodnih optičnih in vezavnih lastnosti ter možnosti radiofluoriranja obetavna molekulska sonda za diagnosticiranje tauopatij. Predviden je bil njen metabolizem in zasnovana sintezna pot za sintezo matične molekulske sonde in treh njenih predvidenih metabolnih produktov. V laboratoriju sta bila izvedena dva koraka sinteze 2-(1-(4-((4-((2-(fluoro)etil)amino)fenil)etinil)fenil)etiliden)malononitrila: jodiranje komercialno dostopnega anilinskega derivata in spajanje po Sonogashiri z mebinolom. Preostala sintezna pot je bila začrtana teoretično. Vključuje tvorbo terminanega acetilena, ki se ga lahko s ponovno reakcijo po Sonogashiri spoji z bromoacetofenonom. Po fluoriranju z DAST in Knoevenagelovi kondenzaciji z malononitrilom lahko sintetiziramo končna produkta 2-(1-(4-((4-((2-(fluoro)etil)amino)fenil)etinil)fenil)etiliden)malononitril in 2-(1-(4-((4-(etil(2-(fluoro)etil)amino)fenil)etinil)fenil)etiliden)malononitril.

• Jezik: Slovenski jezik
• Ključne besede: molekulska sonda, metaboliti, sinteza, spajanje po Sonogashiri
• Vrsta gradiva: Diplomsko delo/naloga
• Tipologija: 2.11 - Diplomsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2020
• PID: 20.500.12556/RUL-119652
• COBISS.SI-ID: 30485507
• Datum objave v RUL: 10.09.2020

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Synthesis of possible metabolic products of an FDDNP analogue

Izvleček

2-(1-(4-((4-(Ethyl(2-(fluoro)ethyl)amino)phenyl)ethynyl)phenyl)ethylidene)-malononitrile was found to be a promising molecular probe in diagnosticizing tauopathies due to its favorable optical and binding properties, as well as radiofluorinating possibility. Its metabolism was predicted and a synthetic pathway of the parent molecular probe and its three predicted metabolites was proposed. Started by iodination of a commercially available aniline derivative and followed by Sonogashira coupling to mebynol, the first two steps of the syntheis of 2-(1-(4-((4-((2-(fluoro)ethyl)amino)phenyl)ethynyl)phenyl)ethylidene)-malononitrile were performed. The rest of the synthesis was designed theoretically, including the formation of terminal acetylene, Sonogashira coupling to bromoacetophenone, DAST fluorination and Knoevenagel condensation, introducing the final malononitrile.

• Ključne besede: molecular probe, metabolites, synthesis, Sonogashira coupling