Sinteza derivata harmina s potencijalnim antimalarijskim djelovanjem

master's thesis

• Title (english): Synthesis of harmine derivatives with potential antimalarial activity
• Author: Arben Beriša
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Committee member: Tatjana Gazivoda Kraljević (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-09-24, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

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.

Abstract (english)

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.

• Keywords: harmin; azidni derivati cimetne kiseline; 1 2 3-triazoli; antimalarijska aktivnost
• Keywords (english): harmine; azide derivatives of cinnamic acid azide; 1 2 3-triazoles; antimalarial activity
• Language: croatian
• URN:NBN: urn:nbn:hr:149:522657
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-07-23 09:14:38