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undergraduate thesis
Sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. urn:nbn:hr:149:172986
Šljubura, Corina
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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Šljubura, C. (2021). Sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:172986

Šljubura, Corina. "Sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:172986

Šljubura, Corina. "Sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2021. https://urn.nsk.hr/urn:nbn:hr:149:172986

Šljubura, C. (2021). 'Sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:172986

Šljubura C. Sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2021 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:172986

C. Šljubura, "Sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2021. Available at: https://urn.nsk.hr/urn:nbn:hr:149:172986

Metadata
TitleSinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina
Title (english)Synthesis and structural characterization of new N-substituted derivatives of imidazo[4,5-b]pyridine
AuthorCorina Šljubura
MentorMarijana Hranjec (mentor)
Committee memberMarijana Hranjec (predsjednik povjerenstva)
Committee memberDragana Vuk (član povjerenstva)
Committee memberKristina Starčević (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2021-07-14, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
Derivati imidazo[4,5-b]piridina, svestrani purinski izosteri, važna su skupina heterocikličkih spojeva jer pokazuju širok spektar biološkog djelovanja. U ovom radu opisana je sinteza i strukturna karakterizacija novih N-supstituiranih derivata imidazo[4,5-b]piridina. Ciljani spojevi priređeni su klasičnim reakcijama organske sinteze te sinteze potpomognute mikrovalovima. U prvom koraku sinteze, mikrovalovima potpomognutom aminacijom 2-klor-3-nitropiridina 1 uz odgovarajući amin priređeni su spojevi 2 i 3. Diamino supstituirani derivati 4 i 5 priređeni su redukcijom kataliziranom s Pd/C. Iz spojeva 4 i 5 u reakciji ciklokondenzacije s esterom priređeni su glavni prekursori 7, 8 i 9. Reakcijom aldolne kondenzacije iz glavnih prekursora 7, 8 i 9 te odgovarajućih aromatskih aldehida 10-12 priređeni su iminokumarinski derivati 13-23. Amino supstituirani iminokumarin 18 priređen je redukcijom spoja 17 s SnCl2x2H2O. Kod spojeva 20 i 22 utvrđeno je postojanje smjese iminokumarina i pentacikličkog derivata 21 i 23. Kolonskom kromatografijom iz smjese su uspješno razdvojeni spojevi 20 i 21, dok je iz smjese spoja 22 izoliran samo pentaciklički derivat 23. Strukture novopriređenih spojeva potvrđene su 1H i 13C NMR spektroskopijom, kao i MS spektrometrijom. Ispitana je antioksidativna aktivnost priređenim spojevima metodama DPPH i FRAP.
Abstract (english)
Imidazo[4,5-b]pyridine derivatives, versatile purine isosters, are an important group of heterocyclic compounds since they exhibit a broad spectrum of biological activity. This work describes the synthesis and structural characterization of new N-substituted derivatives of imidazo[4,5-b]pyridine. The targeted compounds were prepared by using the standard reactions of organic synthesis and microwave-assisted synthesis. In the first step of the synthesis, compounds 2 and 3 were prepared by microwave-assisted amination of 2-chloro-3-nitropyridine 1 with the corresponding amine. Diamino-substituted derivatives 4 and 5 were prepared by the reduction of catalyzed by Pd/C. The main precursors 7, 8 and 9 were prepared from compounds 4 and 5 in reaction cyclocondensations with ester. Iminocoumarin derivatives 13-23 were prepared in the reaction of aldol condensation from the main precursors 7, 8 and 9 and the corresponding aromatic aldehydes 10-12. Amino-substituted iminocoumarin 18 was prepared by reduction of the compound 17 with SnCl2x2H2O. Compounds 20 and 22 were found to have mixtures of iminocoumarins and pentacyclic derivatives 21 and 23. Column chromatography was used to separate compounds 20 and 21, while only pentacyclic derivative 23 was isolated from mixture 22. The structures of the newly prepared compounds were confirmed by 1H and 13C NMR spectroscopy as well as MS spectrometry. The antioxidative activity of prepared compounds was determinate by using DPPH and FRAP method.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:172986
ProjectNumber: IP-2018-01-4379
Title: Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensa
Acronym: AntioxPot
Leader: Marijana Hranjec
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
Study programmeTitle: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry
Course: Applied organic chemistry
Study programme type: university
Study level: undergraduate
Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
Type of resourceText
File originBorn digital
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Created on2023-04-24 09:42:03