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undergraduate thesis
Sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. urn:nbn:hr:149:521202
Kurajica, Livia
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Kurajica, L. (2015). Sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:521202

Kurajica, Livia. "Sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:521202

Kurajica, Livia. "Sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:521202

Kurajica, L. (2015). 'Sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 26 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:521202

Kurajica L. Sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2015 [cited 2024 November 26] Available at: https://urn.nsk.hr/urn:nbn:hr:149:521202

L. Kurajica, "Sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2015. Available at: https://urn.nsk.hr/urn:nbn:hr:149:521202

Metadata
TitleSinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama
Title (english)Synthesis of C-5 substituted cytosine derivatives by palladium catalysed reactions
AuthorLivia Kurajica
MentorTatjana Gazivoda Kraljević (mentor)
Committee memberTatjana Gazivoda Kraljević (predsjednik povjerenstva)
Committee memberMaja Stipković Babić (član povjerenstva)
Committee memberSvjetlana Krištafor (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2015-07-13, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
U ovom radu opisana je sinteza C-5 supstituiranih citozinskih derivata paladijem kataliziranim reakcijama. Sonogashira-inom reakcijom unakrsnog spajanja N-4-benzoil-5-jodcitozin (1) s terminalnim alkinima dobiveni su 5-alkinilni derivati citozina (2−4) te C-6-alkilni derivat pirolo[2,3-d]pirimidina 5. Triazolni prsten u položaj N-1 citozina uveden je „klik“ reakcijom potpomognutom mikrovalovima N-1-propagiliranog derivata citozina 6 s odgovarajućim azidima pri čemu su nastali spojevi 7−9. 5-alkinilni derivati citozina 10−11 s triazolnim supstituentom u položaju N-1 pripravljeni su Sonogashira-inom reakcijom 5-jod-N-1-metiltriazolnog derivata citozina 7 s odgovarajućim terminalnim alkinima. Strukturna karakterizacija novih derivata citozina provedena je 1H NMR spektroskopijom. Farmakološki učinci i moguće biološke mete predviđeni su in silico analizom (PASS). Citostatska ispitivanja in vitro novosintetiziranih spojeva 2, 5 i 7 provedena su na staničnim linijama HeLa (adenokarcinom vrata maternice), CaCo-2 (adenokarcinom debelog crijeva), Raji (Burkittov limfom) i K562 (kronična mijeloidna leukemija u blastičnoj fazi). Spoj 7 pokazao je umjereno djelovanje protiv stanične linije K562. Kako bi se odredili mogući mehanizmi bioloških djelovanja spojeva ispitana je interakcija spoja 7 s ct-DNA UV/Vis i fluorescencijskom spektroskopijom.
Abstract (english)
This paper describes the synthesis of C-5 substituted cytosine derivatives by palladium catalysed reaction. 5-alkyl citosyne derivatives 2−4 and C-5 alkynylpyrolo[2,3-d]pirimidine derivative 6 have been synthesized by Sonogashira cross-coupling reaction of N-4-benzoyl-5-iodinecytosine (1) with terminal alkynes. N-1 triazole ring was introduced into N-1 position of cytosine derivatives 7−9 using „click“ reaction with corresponding azides under microvawe irradiation. 5-alkyl cytosine derivatives 10−11 with triazole substituent in position N-1 have been synthesized by Sonogashira cross coupling of 5-iodo-N-1-methyltriazole cytosine (7) with corresponding terminal alkyne. Structural characterization of synthesized compounds was conducted using 1H NMR spectroscopy. Pharmacological effects and potential bilogical targets of novel compounds have been predicted by in silico analysis (PASS). Cytostatic evaluation in vitro was preformed against human malignant tumor cells: HeLa, CaCo-2, Raji and K562. Compound 7 showed moderate cytotoxic effect against K562 tumor cell lines. Interaction of compound 7 with ct-DNA was performed by UV/Vis and fluorescence spectroscopy in order to predict mechanism of cytostatic activity.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:521202
Study programmeTitle: Environmental Engineering - Undergraduate study
Study programme type: university
Study level: undergraduate
Academic / professional title: sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka ekoinženjerstva (sveučilišni/a prvostupnik/ prvostupnica (baccalaureus/baccalaurea) inženjer/inženjerka ekoinženjerstva)
Type of resourceText
File originBorn digital
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Created on2016-09-13 08:46:31