Ferocenski asimetrični kurkuminoid-pirazoli: sinteza i strukturna karakterizacija

undergraduate thesis

• Title (english): Ferrocene-containing asymmetric curcuminoid pyrazoles: synthesis and structure characterization
• Author: Tea Lukačević
• 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: 2019-09-18, Croatia
• Scientific / art field, discipline and subdiscipline: BIOTECHNICAL SCIENCES; Biotechnology

Abstract

Kurkumin, glavni polifenolni spoj prisutan u korijenu biljke Curcuma longa, posjeduje razna farmakološka svojstva. Unatoč brojnim pozitivnim djelovanjima, iskorištenje kurkumina u organizmu je iznimno nisko te su provedena mnoga istraživanja kako bi se poboljšala njegova biodostupnost pri čemu glavnu ulogu ima sinteza strukturnih analoga kurkumina. Cilj ovoga rada je sinteza i strukturna karakterizacija novih ferocenom deriviranih kurkuminoid-pirazola u svrhu ispitivanja njihove antioksidativne, antimikrobne i antitumorne aktivnosti te usporedbe s aktivnošću koju pokazuje kurkumin. Za sintezu analoga kurkumina korišten je ferocenilaceton (1), ferocenski spoj koji je ranije poznat u literaturi. Sintetizirani su sljedeći novi spojevi: ferocenski β-diketonski analog kurkumina 2 te ferocenski kurkuminoid-pirazoli 3, 4 i 5 u sljedećim iskorištenjima: 2-54%, 3-50%, 4-47% i 5-33%. Strukture dobivenih spojeva potvrđene su IR- i NMR-spektroskopijom.

Abstract (english)

Curcumin, the main polyphenol compound found in the rhizome of the plant Curcuma longa, possesses various pharmacological properties. Despite its numerous positive effects, bioavailability of curcumin is extremely poor. Consequently many studies have been conducted in order to improve its bioavailability, wherein the leading role is given to the synthesis of curcumin analogues. The aim of this thesis was the synthesis and structure characterization of new ferrocene derived curcuminoid pyrazoles for the purpose of testing their antioxidant, antimicrobial and antitumor activities in comparison with the biological activities of curcumin. Ferrocenylacetone (1), ferrocene compound formerly mentioned in the literature, was used for the synthesis of curcumin analogues. The following new compounds were synthesized: ferrocene β-diketone curcumin analogue 2 and ferrocene curcuminoid pyrazoles 3, 4 and 5 in the following yields: 2-54%, 3-50%, 4-47% i 5-33%. The structures of obtained compounds were confirmed by IR and NMR spectroscopy.

• Keywords: analozi kurkumina; ferocen; kurkumin; pirazoli
• Keywords (english): curcumin; curcumin analogues; ferrocene; pyrazoles
• Language: croatian
• URN:NBN: urn:nbn:hr:159:081414
• 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: Access restricted to students and staff of home institution
• Created on: 2019-09-23 09:14:02