University of Zagreb. Faculty of Chemical Engineering and Technology.
Abstract
Cilj ovog rada bila je regioselektivna sinteza 1,4-disupstituiranih-1,2,3-triazolnih derivata L-askorbinske kiseline (2–11) kao spojeva s potencijalnim antitumorskim djelovanjem. 1,2,3-triazolni derivati (2–8) pripravljeni su reakcijom 1,3-dipolarne cikoladicije koja se temelji na konceptu “klik” kemije uz Cu(I) kao katalizator. Za sintezu spojeva 2–8 koristila se tandemska reakcija tosiliranog derivata L-askorbinske kiseline (1) i odgovarajućih terminalnih alkina bez izoliranja azidnog derivata L-askorbinske kiseline koji nastaje kao međuprodukt. Sinteze spojeva 2–8 su se provodile primjenom mikrovalova pri temperaturi od 80 °C i 300 W. Kako bi se ispitalo antioksidativno djelovanje 1,2,3-triazolnih derivata L-askorbinske kiseline, priređeni su derivati L-askorbinske kiseline 9−11 sa slobodnim hidroksilnim skupinama uklanjanjem benzilne zaštite. Strukture svih sintetiziranih spojeva (2–11) potvrđene su 1H- i 13C-NMR spektroskopijom.The aim of this work was the synthesis of 1,4-disubstituted 1,2,3-triazole derivatives of L-ascorbic acid (2–11) with potential antiproliferative activity using regioselective approach. 1,2,3-triazole derivatives (2–8) were prepared using 1,3-dipolar cycloaddition reaction based on the concept of "click" chemistry with Cu(I) as a catalyst. For the synthesis of compounds 2–8 tandem reaction of the tosylated L-ascorbic acid derivative (1) and corresponding alkynes was used without the isolation of the C-6 azide L-ascorbic acid derivative. The synthesis of compound 2–8 was conducted using microwave irradiation at 80 °C and 300 W. In order to explore the antioxidant properties of the 1,2,3-triazole L-ascorbic acid derivatives, compounds 9–11 with free hydroxyl groups were prepared by removal of the benzyl protection. The structures of all compounds (2–11) have been confirmed by 1H- and 13C-NMR spectroscopy
