Hidrazidi kao prekursori za sintezu heterocikličkih, biološki aktivnih spojeva

undergraduate thesis

• Title (english): Hydrazides as precursors for the synthesis of heterocyclic, biologically active compounds
• Author: Iva Mandić
• Mentor: Veronika Kovač (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: 2018-07-16, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Food Technology

Abstract

Cilj ovoga rada bila je sinteza ferocenskih hidrazida kao prekursora za dobivanje heterocikličkih pirazolnih derivata kurkumina čija će se biološka aktivnost ispitivati na raznim linijama tumorskih stanica. Sinteza ciljnih spojeva provedena je korištenjem dva postupka (A i B) kako bi se odredila efikasnost pojedinog sintetskog puta na temelju dobivenih iskorištenja produkata. Postupkom A, iz ferocenskih kiselina 1, 2 i 3 HOBt/EDC metodom sintetizirani su ferocenski hidrazidi 7 (37%), 8 (69%) i 9 (66%), a u postupku B, reakcijom metilnih estera ferocenske kiseline 4, 5 i 6 s hidrazin hidratom dobiveni su ferocenski hidrazidi u većim iskorištenjima (7-63%, 8-84%, 9- 82%). Sintetski put B pokazao se efikasnijim, a za oba postupka vrijedi da se veća iskorištenja postižu u reakcijama u kojima karboksilna skupina nije direktno vezana na ferocenski prsten. Strukture dobivenih spojeva potvrđene su IR- i NMR-spektroskopijom.

Abstract (english)

The aim of this thesis was the synthesis of ferrocene hydrazides as precursors for the formation of heterocyclic pyrazole derivatives of curcumin whose biological activity will be tested on different lines of tumor cells. Synthesis of the target compounds was performed by two methods (A and B) to determine the efficiency of a particular synthetic route based on the obtained results. By the method A, ferrocene hydrazides 7 (37%), 8 (69%) and 9 (66%) were synthesized from the ferrocene acids 1, 2 and 3 using HOBt/EDC method. The reactions of ferrocene methyl esters 4, 5 and 6 with hydrazine hydrate (method B) gave ferrocene hydrazides in greater yields (7-63%, 8-84%, 9-82%). The synthetic route B was more efficient, whereas with the both methods greater yields in reactions in which the carboxyl group is not directly bound to ferrocene ring were achieved. The structures of obtained compounds were confirmed by IR- and NMR spectroscopy.

• Keywords: ferocen; hidrazid; heterociklički spojevi; HOBt/EDC metoda
• Keywords (english): ferrocene; hydrazides; heterocyclic compounds; HOBt/EDC method
• Language: croatian
• URN:NBN: urn:nbn:hr:159:736781
• Study programme: Title: Food Technology; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka prehrambene tehnologije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2018-07-19 11:24:09