Sinteza novih piridin-oksimskih i ferocen-oksimskih derivata kao potencijalnih antitumorskih agensa

undergraduate thesis

• Title (english): Synthesis of novel pyridin-oxime and ferrocene-oxime derivatives as potential antitumor agents
• Author: Klara Vitković
• 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: 2022-09-26, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada bila je sinteza novih piridin-oksimskih (49–52, 54–62) i ferocenoksimskih derivata (46–48, 53) kao potencijalnih antitumorskih agensa. U tu svrhu provedena je sinteza piridin-2-aldoksima (49) te naknadno njegovo O-alkiliranje. Provedena je zatim sinteza mono- i bis-ferocenskih azida (45a, 45b) iz ferocen alkohola. Reakcijom 1,3-dipolarne cikloadicije terminalnog alkina i ferocenskog azida dobiveni su mono- i bis-supstituirani ferocen-oksimski-1,2,3-triazolni derivati (46, 48, 53). U ovom radu također je provedeno uvođenje benzoilne zaštitne skupine na uracilu, 5-kloruracilu i timinu. Potom su provedene reakcije nukleofilne supstitucije uracila, 5-kloruracila i timina, sa i bez zaštitne skupine, s brometil-piridin-2-aldoksimom (52). U obje reakcije dobiveni su mono- i bis-derivati (57–62). Strukture novopripravljenih spojeva potvrđena je 1H i 13C NMR spektroskopijom.

Abstract (english)

The goal of this work was the synthesis of new pyridine-oxime (49–52, 54–62) and ferrocene-oxime derivatives (46–48, 53) as potential antitumor agents. For this purpose, the synthesis of pyridine-2-aldoxime (49) and subsequent its O-alkylation were carried out. The synthesis of mono- and bis-ferrocene azides (45a, 45b) from ferrocene alcohol was also carried out. By the 1,3-dipolar cycloaddition reaction of terminal alkyne and ferrocene azide, monoand bis-substituted ferrocene-oxime derivatives (46, 48, 53) were obtained. In this work, the introduction of a benzoyl protecting group on uracil, 5-chloro-uracil and thymine moiety was also carried out. Nucleophilic substitution reactions of uracil, 5-chlorouracil and thymine, with and without protecting group, were then carried out with bromomethyl-pyridine-2-aldoxime (52). In both reactions, mono- and bis-derivatives (57–62) were obtained. The structures of newly synthesised compound were confirmed by 1H and 13C NMR spectroscopy.

• Keywords: piridin-oksim; ferocen-oksim; antitumorski agensi; 1 3-dipolarna cikloadicija; nukleofilna supstitucija
• Keywords (english): pyridine-oxime; ferrocene-oxime; antitumor agents; 1 3-dipolar cycloaddition; nucleophilic substitution
• Language: croatian
• URN:NBN: urn:nbn:hr:149:968800
• 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: 2023-03-14 12:16:54