Sinteza i spektralna analiza modificiranih nukleozida uracila

master's thesis

• Title (english): The synthesis and spectral analysis of modified uracil nucleosides
• Author: Matej Ivanović
• Mentor: Jasmina Lapić (mentor)
• Committee member: Senka Djaković (predsjednik povjerenstva)
• Committee member: Valerije Vrček (član povjerenstva)
• Committee member: Igor Stuparević (član povjerenstva)
• Granter: University of Zagreb; Faculty of Food Technology and Biotechnology; (Department of Chemistry and Biochemistry); (Laboratory for Organic Chemistry); Zagreb
• Defense date and country: 2024-05-29, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Biokonjugati ferocena i pirimidinskih baza, zbog svojih elektrokemijskih svojstava i biološke aktivnosti, predstavljaju zanimljive spojeve u polju medicinske kemije. U ovom radu provedena je sinteza novih modificiranih nukleozida uracila, odnosno 1'-metoksikarbonilferocenoil-uracil derivata. Aciliranje se provodi s 1'-metoksikarbonilferocenoil kloridom pri različitim reakcijskim uvjetima. U reakcijama uz natrijev hidrid u dimetilformamidu nastaje isključivo N1-kopulat, dok u acetonitrilu uz trietilamin uočeno je nastajanje N1/N3-kopulata uz N1-kopulat, pri čemu na sam njihov međusobni udio utječe supstituent na C5-položaju uracila. Kao produkt reakcije nastaje N1-kopulata ili smjesa N1- i N1-/N3-kopulata. Strukture novosintetiziranih spojeva potvrđene su IR i NMR spektroskopijom.

Abstract (english)

Bioconjugates of ferrocene and pyrimidine bases, due to their electrochemical properties and biological activities, represent interesting compounds in the field of medicinal chemistry. In this study, the synthesis of new modified uracil nucleosides, namely 1'-methoxycarbonylferrocenoyl-uracil derivatives, was performed. Acylation was carried out with 1'-methoxycarbonylferrocenoyl chloride under various reaction conditions. In reactions using sodium hydride in dimethylformamide, exclusively N1-couplates are formed, while in acetonitrile with triethylamine, the formation of N1/N3-couplated along with N1- couplated was observed, where the substituent at the C5-position of uracil influences the ratio between them. The product of the reaction is either N1-couplate or a mixture of N1- and N1/N3-couplates. The structures of the newly synthesized compounds were confirmed by IR and NMR spectroscopy.

• Keywords: ferocen; uracil; derivati uracila; spektralna analiza
• Keywords (english): ferrocene; uracil; uracil derivatives; spectral analysis
• Language: croatian
• URN:NBN: urn:nbn:hr:159:654178
• Study programme: Title: Molecular Biotechnology; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka molekularne biotehnologije (magistar/magistra inženjer/inženjerka molekularne biotehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-07-25 12:17:05