Sinteza i karakterizacija novih izoksazolnih derivata uracila s potencijalnom antitumorskom aktivnošću

undergraduate thesis

• Title (english): Synthesis and characterization of novel isoxazole uracil derivatives as potential antitumor agents
• Author: Lorena Damjanović
• Mentor: Silvana Raić-Malić (mentor)
• Committee member: Silvana Raić-Malić (predsjednik povjerenstva)
• Committee member: Tatjana Gazivoda Kraljević (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-09-16, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih uracilnih i piridinskih derivata povezanih izoksazolnom poveznicom 6a–f. N-propargilirani derivati uracila 5a–f priređeni su reakcijom alkiliranja. Odgovarajući oksim (3) potreban za sintezu izoksazolnih derivata priređen je reakcijom kloriranja piridin-2-aldoksima. Ciljani derivati 6a–f priređeni su potom bazno kataliziranom 1,3-dipolarnom cikloadicijom iz propargiliranih derivata 5a–f i kloriranog oksima 3. Dobiveni izoksazolni derivati 6a–f korišteni su kao ligandi za sintezu Re(I) kompleksa 7a–f. Nadalje, dobiveni 5-joduracilni derivat supstituiran je u položaju C-5 uporabom paladij-bakar katalizirane Sonogashire reakcije unakrsnog spajanja. Strukture novosintetiziranih spojeva potvrđene su spektroskopijom 1H i 13C NMR. Naknadno će se provesti antitumorska ispitivanja novosintetiziranih spojeva.

Abstract (english)

In this work the synthesis of novel uracil and pyridine derivatives linked via isoxazole spacer (6a–f) is described. N-propargylated uracil derivatives 5a–f were prepared by alkylation reaction. The corresponding oxime 3 for the synthesis of isoxazole derivatives was synthesized by the chlorination reaction of pyridine-2-aldoxime. The targer isoxazole derivatives 6a–f were prepared by base-catalyzed 1,3-dipolar cycloaddition of propargylated uracil derivatives 5a–f and chlorinated oxime 3. Synthesized isoxazole derivatives 6a–f were subsequently used as ligands for the synthesis of Re(I) complexes 7a–f. They were also functionalized at C-5 position of uracil moiety using Sonogashira cross-coupling reaction. The structures of all compounds were determined by 1H NMR and 13C NMR spectroscopy. Anticancer evaluations of these compounds will be performed.

• Keywords: uracil; izoksazol; 1 3-dipolarna cikloadicija; metalni kompleksi
• Keywords (english): uracil; isoxazole; 1 3-dipolar cycloaddition; metal complexes
• Language: croatian
• URN:NBN: urn:nbn:hr:149:723525
• 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: 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: Closed access
• Created on: 2023-02-22 12:40:47