Priprava i spektralna karakterizacija derivata ferocena i ciprofloksacina povezanih triazolnom poveznicom

undergraduate thesis

• Title (english): Synthesis and spectral characterization of ferrocene and ciprofloxacin derivates connected by a triazole linker
• Author: Karla Smrekar
• Mentor: Jasmina Lapić (mentor)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2024-07-10, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Zbog povećanja bakterijske rezistencije i borbe protiv bolesti koje i dalje nisu izlječive, velika je potreba za novim lijekovima koji imaju širi spektar djelovanja, veću efikasnost i manju toksičnost. Cilj ovog rada je sintetizirati spoj koji sadrži tri različite biološki aktivne komponente – ciprofloksacin, ferocen i triazol. Sintetizirani su intermedijeri, 1-azidoetilferocen (3) i metil-N-propagil-1-ciklopropil-6-fluoro-4-okso-7-(4-prop-2-inil-piperazin1-il)-1,4-dihidrokinolin-3-karboksilat (5), uz iskorištenje reakcija oko 80 %. Triazolni prsten je uveden reakcijom "klik-kemije", odnosno 1,3-dipolarnom cikloadicijom ferocenskog azida 3 i metilnog estera propargiliranog ciprofloksacina 5 u prisutnosti katalizatora bakra pri čemu je dobiven 1-4-(1-feroceniletil-1H-1,2,3-triazol-1-il)metil]-metil-1-ciklopropil-6-fluoro-4-okso-7- (4-prop-2-inil-piperazin-il)1,4-di-hidrokinolin-3-karboksilata (6). Iskorištenje ove reakcije je iznosilo 63 %. Struktura svih priređenih spojeva potvrđena je IR i NMR spektroskopijom.

Abstract (english)

Due to the increase in bacterial resistance and the fight against still incurable diseases, there is a great need for new broad-spectrum drugs that have greater efficiency and are less toxic. The aim of this thesis is to synthesize a compound containing three different biologically active components – ciprofloxacin, ferrocene and triazole. The intermediates, 1- azidoethylferrocene (3) and methyl-N-propagyl-1-cyclopropyl-6-fluoro-4-oxo-7-(4-prop-2-ynylpiperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate (5), were synthesized in a reaction yield of about 80 %. The triazole ring was imported by a "click-chemistry" reaction, i.e. 1,3-dipolar cycloaddition of ferrocene azide 3 and methyl ester of propargylated ciprofloxacin 5 in the presence of a copper catalyst, whereby 1-[4-(1-Ferrocenylethyl-1H-1,2,3-triazole-1-yl)methyl]- methyl-1-cyclopropyl-6-fluoro-4-oxo-7-(4-prop-2-ynyl-piperazin-yl)1,4-dihydroquinolin-3-carboxylate (6) was synthesized. The yield of this reaction was 63 %. The structure of all prepared compounds was confirmed by IR and NMR spectroscopy.

• Keywords: ferocen; ciprofloksacin; 1 2 3-triazol; klik-kemija
• Keywords (english): ferrocene; ciprofloxacin; 1 2 3-triazole; click-chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:159:845199
• Study programme: Title: Biotechnology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-11-11 13:39:39