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U ovom radu provedena je sinteza novih biološki aktivnih 1,4-disupstituiranih 1,2,3-triazolnih derivata harmina i cimetne kiseline. Kako bi se pripravili različito supstituirani propargilirani derivati prvotno se provelo prevođenje metoksi skupine harmina u hidroksilnu skupinu (1). Slijedi reakcija s propargil bromidom u suvišku cezijeva karbonata, pri čemu su izolirani 7-propargilirani (2) i 7,9-dipropargilirani harmin (3). Propargiliranje u položaju 9 (4) provedeno je izravno iz harmina uz natrijev hidrid. 7-propargilirani (2) i 7,9-dipropargilirani harmin (3) dalje podliježu bakrom(I) kataliziranoj reakciji Huisgenove 1,3-dipolarne cikloadicije s različito supstituiranim azidima cimetne kiseline i njezinim derivatima (9a-9h, 10), čime su sintetizirani 1,2,3-triazolni hibridi harmina i derivata cimetne kiseline (5, 6a-6h, 7). Strukture svih priređenih spojeva karakterizirane su 1H i 13C NMR spektroskopijom. Ispitivanje antimalarijske aktivnosti na novosintetiziranim triazolnim derivatima harmina je u tijeku. The purpose of this diploma work was to synthesize novel biologically active 1,4-disubstituted 1,2,3-triazole derivatives of harmine and cinnamic acid. In order to prepare variety of propargyl derivatives, methoxy group of the harmine has been converted into the hydroxyl group (1). The reaction of 1 with propargyl bromide is followed by the excess of cesium carbonate, whereby 7-propargyl (2) and 7,9-dipropargyl harmine (3) derivatives were isolated. The propargylation at position 9 (4) was performed directly from the harmine in the presence of sodium hydride. 7-Propargyl (2) and 7,9-dipropargyl harmine are subjected to copper(I) catalysed Huisgen's 1,3-dipolar cycloaddition reaction with differently substituted azides of cinnamic acid and their derivatives (9a-9h, 10) to synthesize 1,2,3-triazole hybrid of harmine and cinnamic acid derivatives (5, 6a-6h, 7). The structures of all prepared compounds were characterized by the 1H and 13C NMR spectroscopy. Evaluation of antimalarial activity on the novel synthesized triazole derivatives of harmine is ongoing. |
