Sinteza i karakterizacija novih oksimskih derivata heterostilbena kao potencijalnih reaktivatora kolinesteraza

master's thesis

• Title (english): Synthesis and characterization of novel oxime derivatives of heterostilbenes as potential cholinesterase reactivators
• Author: Ivana Puček
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Sandra Babić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2020-09-29, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U cilju proučavanja djelovanja oksimskih derivata heterostilbena kao reaktivatora kolinesteraza sintetizirani su novi spojevi 15 – 21. Dobivanje željenih spojeva započinje Wittigovom reakcijom kojom su sintetizirani heterostilbeni 1 – 7, koji su Vilsmeier-Haackovim formiliranjem prevedeni u aldehide 8 – 14. Na njima je provedena reakcija u cilju dobivanja oksimskih derivata 15 – 21, koji do sada literaturno nisu poznati. Očekivani produkti bili su cis- i trans- izomeri spojeva 15 – 21, s nizom različitih supstituenata vezanih u para- položaju benzenskog prstena. U konačnici, u svakoj provedenoj reakciji dobivanja oksima nastala su četiri izomera, s obzirom na konfiguraciju dvostruke veze ugljika, te s obzirom na konfiguraciju dvostruke veze između ugljika i dušika oksimske skupine. Svaki dobiveni oksimski derivat 15 – 21 može zauzeti četiri različita izomerna oblika: cis, syn-, trans, syn-, cis, anti-, trans, anti-. Svi novi spojevi okarakterizirani su spektroskopskim metodama, a za one dobivene u dovoljnoj količini bit će ispitana reaktivacijska aktivnost prema humanim enzimima AChE i BChE.

Abstract (english)

For the purpose of studying the effect of oxime derivatives of heterostilbene as a cholinesterase reactivators, new compounds 15 – 21 were synthesized. Starting ompounds 1 – 7 were synthesized using the Wittig reaction, and they are converted to the aldehydes 8 – 14 by Vilsmeier-Haack formylation. In order to obtain previously unknown oximes 15 – 21, oximation was carried out. The expected products were the cis- and trans- isomers of compounds 15 – 21, which contain different substituents bound in the para-position of the benzene ring. Finally, in each reaction of oxime formation, four isomers were obtained, considering to the configuration of the carbon-carbon double bond, and to the double bond between the carbon and nitrogen of the oxime group. Each obtained oxime derivative 15 – 21 can take four different isomeric forms: cis, syn-, trans, syn-, cis, anti-, trans, anti-. All new compounds were characterized by spectroscopic methods, and for those obtained in sufficient quantities, the reactivation activity against human enzymes AChE and BChE will be tested.

• Keywords: heterostilbeni; kolinesteraze; oksimi; reaktivacija AChE i BChE; spektroskopija
• Keywords (english): heterostilbenes; cholinesterases; oximes; AChE and BChE reactivation; spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:944501
• Study programme: Title: Applied Chemistry - Graduate 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: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2022-03-07 16:51:26