Novi triazolni derivati hidroksipiran-4-ona: priprava i biološka aktivnost

master's thesis

• Title (english): Novel triazole hydroxypyran-4-one derivatives: preparation and biological activity
• Author: Ines Žepić
• Mentor: Vesna Petrović Peroković (mentor)
• Committee member: Vesna Petrović Peroković (predsjednik povjerenstva)
• Committee member: Željka Soldin (član povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Ivana Biljan (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2019-12-20, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru ovog diplomskog rada pripravljeno je šest novih 1,2,3-triazolnih derivata odabranih hidroksipiran-4-ona, maltola i kojične kiseline. Triazolni prsten uveden je poznatom klik-reakcijom između terminalnog alkina i azida, bakrom kataliziranom alkin-azidnom cikloadicijom, gdje je kao katalizator korišten kompleksni spoj bakra(II), tetrakis-μ-(acetato)diakvadibakar(II). Terminalni alkini (1 i 2) za klik-reakciju priređeni su propargiliranjem maltola i kojične kiseline, a aromatski azidi 3 i 4 dobiveni su iz meta-trifluoranilina i anilina. Kao treći azidni prekursor korišten je prethodno pripravljen 1-azidoadamantan. Klik-reakcijama iz navedenih azidnih i alkinskih prekursora regioselektivno su dobiveni 1,4-disupstituirani 1,2,3-triazoli 5-10. Spojevima 6, 7 i 9 ispitana je antitumorska aktivnost in vitro, na pet tumorskih staničnih linija (HTC116, MCF-7, NCI-H460, PANC-1, THP-1).

Abstract (english)

In this Master thesis six novel 1,2,3-triazole derivatives of selected hydroxypyran-4-ones, maltol and kojic acid, were prepared. Triazole ring was introduced by famous click-reaction, copper catalyzed alkyne-azide cycloaddition, where a coordination copper(II) compound, tetra-μ-acetatodiaquadicopper(II), was used as a catalyst. Terminal alkynes 1 and 2 used for click-reactions were synthesized by propargylation of maltol and kojic acid, whereas aromatic azides 3 and 4 were prepared from 3-(trifluoromethyl)aniline and aniline, respectively. Third azide precursor for click-reactions was previously synthesized 1-azidoadamantane. Click-reactions of compounds 1-2 and 3-4 as well as 1-azidoadamantane regioselectively gave 1,4-disubstituted triazole products 5-10. Compunds 6, 7 and 9 were tested for their antitumor activity in vitro on five tumour cell lines, namely, HTC116, MCF-7, NCI-H460, PANC-1 and THP-1.

• Keywords: antitumorska aktivnost; azidi; 1; 4-disupstituirani 1; 2; 3-triazoli; propargilirani hidroksipiran-4-oni; klik-reakcije
• Keywords (english): antitumor activity; azides; 1; 4-disubstituted 1; 2; 3-triazoles; propargylated hydroxypyran-4-ones; click-reactions
• Language: croatian
• URN:NBN: urn:nbn:hr:217:118129
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2021-12-20
• Created on: 2020-01-29 11:08:49