Development of synthetic procedure for guanylation employing bis(trimethylsilyl)carbodiimide

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.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