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undergraduate thesis
Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. urn:nbn:hr:149:701141
Orehovački, Petra
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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Orehovački, P. (2015). Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:701141

Orehovački, Petra. "Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:701141

Orehovački, Petra. "Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2015. https://urn.nsk.hr/urn:nbn:hr:149:701141

Orehovački, P. (2015). 'Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:701141

Orehovački P. Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2015 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:701141

P. Orehovački, "Novi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2015. Available at: https://urn.nsk.hr/urn:nbn:hr:149:701141

Metadata
TitleNovi derivati 7-deazapurina: organometalna sinteza i strukturna karakterizacija
Title (english)The novel 7-deazapurine derivatives: organometallic synthesis and structural characterization
AuthorPetra Orehovački
MentorTatjana Gazivoda Kraljević (mentor)
Committee memberTatjana Gazivoda Kraljević (predsjednik povjerenstva)
Committee memberMaja Stipković Babić (član povjerenstva)
Committee memberLidija Furač (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2015-09-08, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
Cilj ovog rada bio je sintetizirati nove N-1 triazolilne i C-5 alkinilne derivate citozina i 7-deazapurina, u svrhu ispitivanja njihove antitumorske aktivnosti protiv tumorskih staničnih linija porijeklom iz čovjeka (Raji, K564, HeLa, CaCo-2). Reakcijom jodiranja N-4-benzoilcitozina pripravljen je N-4-benzoil-5-jodcitozin (1) koji je podvrgnut reakciji N-alkiliranja s propargil-bromidom i NaH kao bazom te je dobiven N-1 alkinilni derivat citozina 2. „Click“ reakcijom kataliziranom bakrom N-1 propargiliranog citozinskog derivata 2 s različito supstituiranim azidima dobiveni su N-1-triazolilni derivati N-4-benzoil-5-jodcitozina (3–5). Sonogashira-inom reakcijom unakrsnog spajanja spojeva 4 i 5 s odgovarajućim terminalnim alkinima, sintetizirani su C-5 alkinilni derivati N-4-benzoil-N-1-triazolilcitozina 6 i 8. 5-endo-dig ciklizacijom in situ spojeva 6 i 8 pripravljeni su C-6 supstituirani derivati 7-deazapurina 7 i 9. Strukture novosintetiziranih spojeva potvrđene su 1H NMR spektroskopijom.
Abstract (english)
The aim of this study was to synthesize the novel N-1 triazolyl and C-5 alkynylated pyrimidine and 7-deazapurine derivatives in order to evaluate their antitumor activities against human malignant tumor cell lines (Raji, K562, HeLa, CaCo-2). N-4-benzoyl-5-iodocytosine (1) was prepared by iodination reaction of N-4-benzoylcytosine which was then subjected to N-alkylation reaction with propargylbromide in the presence of NaH as base to give N-alkynylated cytosine derivative 2. N-1-triazolyl derivatives of N-4-benzoyl-5-iodocytosine (3–5) were obtained via copper catalysed „click“ reaction of N-1-propargylcytosine derivative 2 with corresponding azides. Sonogashira cross-coupling reaction of compounds 4 and 5 with corresponding terminal alkynes gave C-5 alkynylated derivates of N-4-benzoyl-N-1-triazolylcytosine 6 and 8. 7-deazapurine derivatives 7 and 9 were prepared by in situ 5-endo-dig cyclization of the compounds 6 and 8, respectively. The structures of newly synthesized compounds were determined by 1H NMR spectroscopy.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:701141
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
Access conditionsOpen access
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Created on2016-09-26 14:10:10