Priprava i karakterizacija N-acilglicinamida

master's thesis

• Title (english): Preparation and characterization of N-acyl glicine amides
• Author: Matej Pavlinić
• Mentor: Ines Primožič (mentor)
• Committee member: Ines Primožič (predsjednik povjerenstva)
• Committee member: Ivana Kekez (član povjerenstva)
• Committee member: Ivan Nemet (član povjerenstva)
• Committee member: Nikola Cindro (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2024-10-31, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru ovog rada sintetizirana su dva N-acilglicinamida da bi se provjerila njihova inhibitorna svojstva prema enzimu butirilkolinesterazi: N-benzil-N-[2-(tosilmetilamino)-2-oksoetil]- piridin-2-karboksamid i N-benzil-N-[2-(tert-butilamino)-2-oksoetil]benzamid. Oba spoja sintetizirana su višekomponentnom Ugijevom reakcijom, koja se provodila uobičajenim sintetskim metodama, mikrovalovima potpomognutom sintezom i mehanokemijskom sintezom. Provedena je optimizacija uvjeta mikrovalovima potpomognute sinteze N-benzil-N-[2-(tert-butilamino)-2-oksoetil]benzamida. Pripravljenim spojevima određeno je talište te je provedena strukturna analiza korištenjem infracrvene spektroskopije, spektrometrije masa te 1D i 2D spektroskopije nuklearne magnetske rezonancije. Određen je i omjer cis i trans konformera pripravljenih N-acilglicinamida u otopini u protonskim i aprotonskim otapalima različite polarnosti.

Abstract (english)

In this diploma thesis two N-acylglicine amides were synthesized to obtain biactive compounds with inhibitory activity toward butyrylcholinesterase: N-benzyl-N-[2-(tosylmethyleamino)-2- oxoethyle]pyridyne-2-carboxyamide and N-benzyl-N-[2-(tert-buthyleamino)-2-oxoethyle]-benzamide. Both compounds were synthesized via Ugi multicomponent reaction. Reactions were performed using standard synthetic techniques, microwave assisted Ugi reaction as well as mechanochemical techniques. Conditions for the microwave assisted synthesis of N-benzyl-N-[2-(tert-buthyleamino)-2-oxoethyle]benzamide were optimized. The melting points of the prepared compounds were determined, and the structural analysis was performed using infrared spectroscopy, mass spectrometry and 1D and 2D nuclear magnetic resonance spectroscopy. Furthermore, the ratio of cis and trans conformers of prepared N-acylglycinamides in solution in protic and aprotic solvents of different polarity was also determined.

• Keywords: sinteza N-acilglicinamida; Ugijeva reakcija; mehanokemija; mikrovalovima potpomognuta sinteza
• Keywords (english): N-acylglicine amide synthesis; Ugi reaction; mechanochemistry; microwave assisted synthesis
• Language: croatian
• URN:NBN: urn:nbn:hr:217:214697
• Project: Number: 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 programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-11-14 13:11:26