Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazola

undergraduate thesis

• Title (english): Regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles
• Author: Nikolina Stipaničev
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Tatjana Gazivoda Kraljević (član povjerenstva)
• Committee member: Sandra Babić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2015-09-08, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

Cilj ovog rada bila je sinteza novih 1,4-disupstituiranih 1,2,3-triazolnih derivata s 7-deazapurinom i 7-hidroksikumarinom kao potencijalnih biološki aktivnih spojeva. Azidni derivat 6-klor-7-deazapurina 2, kao ključni prekursor, pripravljen je iz N-brometilnog derivata 7-deazapurina 1. Derivati 6-klor-7-deazapurina i 1,2,3-triazola (3 - 13) međusobno povezanih etinilnom premosnicom pripravljeni su ”click” reakcijom potpomognutom mikrovalovima organskog azida i terminalnih alikina kataliziranom bakrom. Nadalje, Huisgenovom 1,3-dipolarnom cikloadicijom pripravljeni su derivati 1,2,3-triazola i 7-hidroksikumarina (14 - 17) iz kumarinskog azida i odgovarajućih terminalnih alkina.
Strukture svih pripravljenih spojeva potvrđene su 1H i 13C NMR spektroskopijom.
Provedena su ispitivanja antibakterijskog djelovanja spojeva 14 - 17 na osam bakterijskih vrsta (četiri Gram-pozitivne i četiri Gram-negativne beakterijske vrste). Spojevi 16 i 17 pokazali su bolju učinkovitost na Gram-pozitivne bakterije Enterococcus faecali od antibiotika ceftazidima (CAZ) i ciprofloksacina (CIP).

Abstract (english)

The aim of this work was the synthesis of novel 1,4-disubstituted 1,2,3-triazole derivatives of 7-deazapurine and coumarin as potential biologically active compounds. The organic azide of 6-chloro-7-deazapurine, as a key precursor, was prepared from N-bromoethynyl derivative of the 7-deazapurine 1. Derivatives of 6-chloro-7-deazapurine and 1,2,3-triazole (3 - 13) bound via ethynyl linker were prepared by copper catalyzed "click" chemistry approach under microwave irradiation between organic azides and terminal alkynyl. Furthermore, derivatives of 1,2,3-triazole and 7-hydroxycoumarin (14 - 17) were prepared by Huisgen 1,3-dipolar cycloadition from the coumarin azide and corresponding terminal alkynes.
The structures of all synthesized compounds were confirmed by 1H i 13C NMR spectroscopy.
The anti-bacterial activity of the synthesized compounds 14 - 17 was performed in vitro against four Gram-positive bacterial species and four Gram-negative bacterial species. The MIC values of the tested compounds compared with those of ceftazidime and ciprofloxacine. Compounds 16 and 17 have shown anti-bacterial activity, which was higher than ceftazidime against Gram-negative bacteria Enterococcus faecali.

• Keywords: 1 4-disupstituirani 1 2 3-triazoli; 7-deazapurini; kumarini; 1 3-dipolarna cikloadicija; "click" kemija
• Keywords (english): 1 4-disupstituted 1 2 3-triazoles; 7-deazapurines; coumarines; 1 3-dipolar cycloadition; "click" chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:348086
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Environmental chemistry and green technologies; 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: 2016-11-17 11:33:31