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master's thesis
Priprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu
Zagreb: University of Zagreb, Faculty of Science, 2024. urn:nbn:hr:217:830383
Kaurinović, Maria-Magdalena
University of Zagreb
Faculty of Science
Department of Chemistry

Institutional repository: Repository of the Faculty of Science

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Kaurinović, M. M. (2024). Priprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu (Master's thesis). Zagreb: University of Zagreb, Faculty of Science. Retrieved from https://urn.nsk.hr/urn:nbn:hr:217:830383

Kaurinović, Maria Magdalena. "Priprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu." Master's thesis, University of Zagreb, Faculty of Science, 2024. https://urn.nsk.hr/urn:nbn:hr:217:830383

Kaurinović, Maria Magdalena. "Priprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu." Master's thesis, University of Zagreb, Faculty of Science, 2024. https://urn.nsk.hr/urn:nbn:hr:217:830383

Kaurinović, M. M. (2024). 'Priprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu', Master's thesis, University of Zagreb, Faculty of Science, accessed 23 December 2024, https://urn.nsk.hr/urn:nbn:hr:217:830383

Kaurinović MM. Priprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu [Master's thesis]. Zagreb: University of Zagreb, Faculty of Science; 2024 [cited 2024 December 23] Available at: https://urn.nsk.hr/urn:nbn:hr:217:830383

M. M. Kaurinović, "Priprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu", Master's thesis, University of Zagreb, Faculty of Science, Zagreb, 2024. Available at: https://urn.nsk.hr/urn:nbn:hr:217:830383

Metadata
TitlePriprava novih heterocikličkih inhibitora butirilkolinesteraze temeljenih na imidazolu
Title (english)Synthesis of novel heterocyclic butyrylcholinesterase inhibitors based on imidazole
AuthorMaria-Magdalena Kaurinović
MentorInes Primožič (mentor)
Committee memberInes Primožič (predsjednik povjerenstva)
Committee memberAleksandra Maršavelski (član povjerenstva)
Committee memberAdriana Kenđel (član povjerenstva)
Committee memberNikola Cindro (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Science
(Department of Chemistry)
Zagreb
Defense date and country2024, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
U okviru ovog diplomskog rada sintetizirani su N-metilimidazol-2-karbaldehid počevši od N-metilimidazola. Zatim je uslijedila sinteza N-metilimidazol-2-karbaldehid-oksim-O-metil-etera koristeći N-metilimidazol-2-karbaldehid i O-metilhidroksilamonijevog klorida. Dobiveni eter oksima je u sljedećem koraku kvaterniziran Menschutkinovom reakcijom korištenjem odgovarajućega alkil-halogenida (metil-jodida, benzil-bromida te različito supstituiranih benzil-bromidima sa supstituentima kao što su nitro skupina i atom halogena u meta i para položaju). Također je provedena Ugijeva reakcija imidazol-2-karbaldehida odnosno N-metilimidazol-2-karbaldehida s benzojevom kiselinom, benzilaminom te tert-butil- izocijanidom ili cikloheksil-izocijanidom. Tijek reakcija praćen je tankoslojnom kromatografijom, a pripravljeni spojevi pročišćeni kromatografijom na stupcu te karakterizirani dostupnim analitičkim metodama (1H i 13C NMR, FTIR, HRMS). Svim pripravljenim spojevima (deset kvaternih etera oksima i tri Ugijeva produkta) određen je inhibitorni potencijal prema enzimu butirilkolinesterazi (BChE, E.C. 3.1.1.8.) izoliranoj iz konjskoga seruma korištenjem Ellmanove metode.
Abstract (english)
In this diploma thesis, N-methylimidazole-2-carbaldehyde was synthesized starting from N- methylimidazole. The synthesis of N-methylimidazole-2-carbaldehyde-oxime-O-methyl using N-methylimidazole-2-carbaldehyde and O-methylhydroxylamine hydrochloride was followed. The resulting oxime was quaternized in the next step using the appropriate alkyl halogenide (methyl iodide, benzyl bromide and differently substituted benzyl bromides with substituents such as a nitro group and halogen atoms in the meta and para positions) by the Menschutkin reaction. The Ugi reaction of imidazole-2-carbaldehyde or N-methylimidazole-2-carbaldehyde, with benzoic acid, benzylamine and tert-butyl isocyanide or cyclohexyl isocyanide was also carried out. This reaction was monitored by thin-layer chromatography, and the prepared compounds were purified by column chromatography and characterized by available analytical methods (1H and 13C NMR, FTIR, HRMS). For all prepared compounds (ten quaternary oxime ethers and three Ugi products), the inhibitory potential against butyrycholinesterase (BChE, E.C. 3.1.1.8.) isolated from horse serum using the Ellman method was determined.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:217:830383
ProjectNumber: IP-2022-10-9525
Title: Metom usmjerena sinteza inhibitora kolinesteraza podržana strojnim učenjem
Title: Target-guided synthesis of cholinesterase inhibitors supported by machine learning
Acronym: TargetCh
Leader: Ines Primožič
Jurisdiction: Croatia
Funder: Hrvatska zaklada za znanost
Funding stream: Research Projects
Study programmeTitle: Graduate university studies in chemistry; specializations in: Graduate university studies in chemistry
Course: Graduate university studies in chemistry
Study programme type: university
Study level: graduate
Academic / professional title: sveučilišni/a magistar/magistra kemije (sveučilišni/a magistar/magistra kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2024-10-22 12:50:14