No public access
master's thesis
Development of synthetic procedure for guanylation employing bis(trimethylsilyl)carbodiimide

Vanda Lovreković (2016)
University of Rijeka
Department of Biotechnology
Metadata
TitleRazvoj sintetskog postupka gvanilacije upotrebom bis(trimetilsilil)karbodiimida
AuthorVanda Lovreković
Mentor(s)Davor Margetić (thesis advisor)
Abstract
Pokušan je razvoj nove sintetske metode za pripravu monosupstituiranih gvanidina reakcijom amina sa bis-TMS karbodiimidom. Metoda nije uspjela radi slabe reaktivnosti korištenog karbodiimida. Primjenom literaturno opisanog reagensa za gvanilaciju, efikasno je pripravljen gvanidin/klorin-e6 131-diaminoetilkarboksamid konjugat i potpuno karakteriziran 1H NMR spektroskopijom. Osim alifatskih amina, za pripravu gvanidin/porfirin konjugata sintetiziran je tetrafenil porfirin, koji je selektivno nitriran, te zatim reduciran u odgovarajući amin. Mala količina dostupnog aminoporfirina dozvolila je samo inicijalno testiranje slijedećeg reakcijskog koraka, priprave 4-benzoiltioureje-TPP konjugata.
KeywordsPorphyrins methyl pheophorbide a photodynamic therapy
Parallel title (English)Development of synthetic procedure for guanylation employing bis(trimethylsilyl)carbodiimide
Committee MembersDavor Margetić (committee chairperson)
Sandra Kraljević Pavelić (committee member)
Karlo Wittine (committee member)
GranterUniversity of Rijeka
Lower level organizational unitsDepartment of Biotechnology
PlaceRijeka
StateCroatia
Scientific field, discipline, subdisciplineBIOTECHNICAL SCIENCES
Biotechnology
Study programme typeuniversity
Study levelgraduate
Study programmeMedicinal chemistry
Academic title abbreviationmag. med. chem.
Genremaster's thesis
Language Croatian
Defense date2016-10-06
Parallel abstract (English)
Development of new synthetic methods for preparing mono-substituted guanidines by reaction of amines with bis-TMS carbodiimide was attempted. The method failed due to poor reactivity of used carbodiimide. Using the literature described guanylation reagent, guanidine/chlorin e6-131-conjugate diaminoethylcarboxamide was prepared effectively and fully characterized by 1H NMR spectroscopy. In addition to aliphatic amines, for the preparation of guanidine/porphyrin conjugates tetraphenyl porphyrin was synthesized, which was selectively nitrated and then reduced to the corresponding amine. A small amount of available aminoporphyrin allowed only initial testing of the next reaction step in preparation of 4-benzoylthiourea-TPP conjugate.
Parallel keywords (Croatian)Porfirini metil feoforbid a fotodinamička terapija
Resource typetext
Access conditionNo public access
URN:NBNhttps://urn.nsk.hr/urn:nbn:hr:193:230209
CommitterIvana Dorotić