Sinteza novih derivata benzotiazola s potencijalnim antitumorskim djelovanjem

undergraduate thesis

• Title (english): Synthesis of novel benzothiazole derivatives with antitumoral potential
• Author: Antonija Mamić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Silvija Maračić (član povjerenstva)
• Committee member: Dragana Mutavdžić Pavlović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-09-17, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu je opisana sinteza novih 1,2,3-triazolnih derivata benzotiazola te njihova strukturna karakterizacija 1H- i 13C-NMR spektroskopijom. Mikrovalovima potpomognutom SN2 reakcijom 2-hidroksibenzaldehida i propargil-bromida uz K2CO3 kao bazu pripravljen je 2-(prop-2-in-1-iloksi)benzaldehid (1). Propargilirani derivat benzotiazola (2) priređen je ciklizacijom 2-O-propargilbenzaldehida (1) i ortho-aminotiofenola u dimetilformamidu uz oksidacijsko sredstvo Na2S2O5. Ciljani 1,2,3-triazolni derivati benzotiazola (3 – 14) sintetizirani su mehanokemijskim reakcijama Huisgenovom 1,3-dipolarnom cikloadicijom 2-(2-(prop-2-in-1-iloksi)fenil)benzo[d]tiazola (2) i odgovarajućih aromatskih azida uz bakrov(II) acetat kao katalizator. Strukture svih novopriređenih spojeva potvrđene su
1H- i 13C-NMR spektroskopijom.

Abstract (english)

This paper describes the synthesis of new 1,2,3-triazolyl benzothiazole derivatives and their structural characterization by 1H- and 13C-NMR spectroscopy. Microwave-assisted SN2 reaction of 2-hydroxybenzaldehyde and propargyl bromide with K2CO3 as a base
2-(prop-2-yn-1-yloxy)benzaldehyde (1) was prepared. A propargylated benzothiazole derivative (2) was prepared by cyclization of 2-O-propargylbenzaldehyde (1) and
ortho-aminothiophenol in dimethylformamide using Na2S2O5 as oxidizing agent. Target 1,2,3-triazolyl benzothiazole derivatives (3 - 14) were synthesized by mechanochemical reactions by Huisgen 1,3-dipolar cycloaddition of
2-(2-(prop-2-yn-1-yloxy)phenyl)benzo[d]thiazole (2) and the corresponding aromatic azides with copper (II) acetate as catalyst. The structures of all newly prepared compounds were confirmed by 1H- and 13C-NMR spectroscopy.

• Keywords: benzotiazol; Huisgenova 1 3-dipolarna cikloadicija; 1 2 3-triazol; klik reakcija; mehanokemijske reakcije; mikrovalovima potpomognute reakcije
• Keywords (english): benzothiazole; Huisgen 1 3-dipolar cycloaddition; 1 2 3-triazole; click reaction; mechanochemical reactions; microwave-assisted reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:847052
• Project: Number: IP-2018-01-4682; Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja; Acronym: PurBioCaPa; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Materials Science and Engineering - Undergraduate study; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-10-01
• Created on: 2023-04-07 08:23:01