Sinteza konjugata kinolina i harmina s potencijalnim antimalarijskim djelovanjem

undergraduate thesis

• Title (english): Synthesis of quinoline and harmine conjugates with potential antimalarial activity
• Author: Rebeka Štulić
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2018-09-17, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U okviru ovog rada provedena je sinteza novih potencijalno biološki aktivnih hibrida kinolina, kumarina i harmina regioselektivnom 1,3-dipolarnom cikloadicijom terminalnih alkina i organskih azida. Spojevi su priređeni konvencionalnom sintetskom metodom koja zadovoljava većinu uvjeta ,,klik“ kemije. Harmin 1 prevodi se u reakciji s propargil-bromidom u 9-(prop-2-inil)harmin 2 koji onda Huisgenovom cikloadicijom s kumarinskim 3 i kinolinskim azidom 4 kataliziranom bakrom(I) daje odgovarajuće 1,2,3-triazolne konjugate 5 i 6. Polazni alkini 8 i 11 za sintezu kumarinskih i kinolinskih 1,2,3-triazola 7-(prop-2-iniloksi)harmina 9, 10 i 9-(prop-2-inil)-7-(prop-2-iniloksi)harmina 12, 13 dobivaju se iz harmola 7. Priređenim spojevima 5, 6, 9, 10, 12 i 13 ispitat će se antimalarijska aktivnost.

Abstract (english)

The aim of this work was the synthesis of novel hybrids containing coumarine, quinoline and harmine moiety with potential biological activity, using regioselective 1,3-dipolar cycloaddition of terminal alkynes and organic azides. Novel compounds were prepared by conventional synthetic approach which fulfills most of ,,click“ chemistry requirements. Harmine 1 is converted with propargyl-bromide to 9-(prop-2-ynyl)harmine 2 which then in Huisgen copper(I) catalyzed cycloaddition with coumarine 3 and quinoline 4 azide gives corresponding 1,2,3-triazole conjugates 5 and 6. Alkynes 8 and 11 needed for the synthesis of coumarine and quinoline 1,2,3-triazoles 7-(prop-2-ynyloxy)harmines 9, 10 and 9-(prop-2-ynyl)-7-(prop-2-ynyloxy)harmines 12, 13 are synthesized starting from harmole 7. Antimalarial activity of prepared compounds 5, 6, 9, 10, 12 and 13 will be performed.

• Keywords: 1 2 3-triazoli; ''click'' kemija; derivati harmina; kinolini; kumarini
• Keywords (english): 1 2 3-triazoles; ''click'' chemistry; harmine derivatives; quinoline; coumarine
• Language: croatian
• URN:NBN: urn:nbn:hr:149:667034
• Project: Number: IP-2013-11-5596; Title: Sinteza i citostatska ispitivanja biblioteke novih dušikovih heterocikla; Title: Synthesis and cytostatic evaluations of novel nitrogen heterocycles library; Acronym: SCIENcENTRY; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Applied Chemistry - Undergraduate 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: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2022-05-10 11:37:47