Novi 3-tienostilbenski oksimi – sinteza i spektroskopska karakterizacija

undergraduate thesis

• Title (english): New 3-thienostilbene oximes - synthesis and spectroscopic characterization
• Author: Amalija Ernečić
• 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: 2021-09-09, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

S ciljem pronalaska novih potencijalnih reaktivatora enzima acetilkolinesteraze inhibiranog djelovanjem organofosfornih živčanih agenasa sintetizirani su novi derivati 3-tienostilbenskih oksima. Wittigovom reakcijom sintetizirani su cis- i trans-heterostilbeni iz 3-tienilnog aldehida i p-supstituiranih fosfonijevih soli kao polazne strukture s ciljem prevođenja u oksim. Tri odabrane soli kao supstituente na benzenskom prstenu sadržavale su metilnu skupinu, klor i cijano-skupinu. Heterostilbeni su funkcionalizirani Vilsmeierovim formiliranjem čime su dobiveni karbaldehidi. Karbaldehidi su u zadnjem sintetskom koraku prevedeni u oksime reakcijom oksimiranja uz hidroksilamin hidroklorid kao reagens. Ukupno je dobiveno i izolirano dvanaest oksima od kojih su četiri oksima s metilnim supstituentom i dva oksima s cijano-supstituentom dobiveni u dovoljnoj količini za biološka istraživanja reaktivacije enzima acetilkolinesteraze. Svi međuprodukti i produkti pročišćeni su kolonskom kromatografijom, a strukture su im okarakterizirane i potvrđene 1H i 13C NMR spektrima.

Abstract (english)

In order to find new potential reactivators of the enzyme acetylcholinesterase inhibited by the organophosphorus nerve agents, new derivatives of 3-thienostilbene oximes were synthesized. Wittig reaction yielded cis and trans heterostilbene isomers that were synthesized from 3-thienyl aldehyde and p-substituted phosphonium salts as the starting structures with the aim of conversion to the oxime. The three selected salts contained methyl, chlorine and a cyano group as a supstituent on the benzene ring. Heterostilbenes were functionalized by Vilsmeier formylation to give carbaldehydes. In the last synthetic step, the carbaldehydes were converted to oximes by an oximation reaction with hydroxylamine hydrochloride as a reagent. A total of twelve oximes were obtained and isolated of which four oximes with methyl substituent and two oximes with cyano substituent were obtained in sufficient quantity for biological studies of acetylcholinesterase enzyme reactivation. All intermediates and products were purified by column chromatography and their structures were characterized and confirmed by 1H and 13C NMR spectra.

• Keywords: heterostilbeni; oksimi; acetilkolinesteraza; Wittig; Vilsmeier; spektroskopija
• Keywords (english): heterostilbenes; oximes; acetylcholinesterase; Wittig; Vilsmeier; spectroscopy
• Language: croatian
• URN:NBN: urn:nbn:hr:149:294639
• Study programme: Title: 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 resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-03-28 07:33:18