20.500.12556/RUL-119652 Sinteza možnih metabolnih produktov analoga FDDNP Synthesis of possible metabolic products of an FDDNP analogue 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. 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. molekulska sonda metaboliti sinteza spajanje po Sonogashiri molecular probe metabolites synthesis Sonogashira coupling true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2020-09-10 09:35:00 2020-09-10 09:35:03 2022-08-31 03:54:07 0000-00-00 00:00:00 2020 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 11001 30485507 Brodnik_Ana_-_Sinteza_moznih_metabolnih_produktov_analoga_FDDNP.pdf Brodnik_Ana_-_Sinteza_moznih_metabolnih_produktov_analoga_FDDNP.pdf 1 CC52AC4BAFE213ED1506E1F131F4AF44 6bf1e72750ee04ca9003faaaf657c0b2d50651da163067698cb01a3f594298ca e29cecf0-a1b9-11eb-a523-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=134377 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0