Fotokemijske transformacije različitih biološki aktivnih derivata resveratrola u šaržnom i protočnom reaktoru

master's thesis

• Title (english): Photochemical transformations of diverse biologically active resveratrol derivatives in batch and flow reactor
• Author: Hana Perinić
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Ivan Karlo Cingesar (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2024-09-30, Croatia
• Scientific / art field, discipline and subdiscipline: TECHNICAL SCIENCES; Chemical Engineering

Abstract

Rezveratrol je stilbenoidni polifenol s različitim antioksidativnim, antitumorskim, neuroprotektivnim i kardioprotektivnim svojstvima, a zbog niske bioraspoloživosti, razvijaju se njegovi biološki aktivni derivati koji pokazuju značajan antioksidativni potencijal i inhibicijsku aktivnost za enzime kolinesteraze, što je dokazano nižim IC50 vrijednostima u odnosu na standardni inhibitor galantamin. U ovom su radu Wittigovom reakcijom sintetizirani heteroaromatski derivati rezveratrola koji su poslužili kao početni spojevi 1-5 za daljnje fotokemijske transformacije u šaržnom i protočnom reaktoru. Fotokemijske transformacije provedene su izravnim osvjetljavanjem početnih spojeva na različitim valnim duljinama ili uz prisutstvo porfirinskog fotokatalizatora s četiri različite LED lampe. Osim valne duljine i fotokatalizatora, u protočnom se reaktoru još mijenjalo vrijeme zadržavanja i temperatura.
Iz rezultata je najviše vidljivo dobivanje cikličkih produkata i trans-cis izomerizacija, a računalnim istraživanjem fotoreaktivnosti početnog spoja 1 utvrđeni su glavni putevi njihova dobivanja. Uspoređujući produktivnost i selektivnost reakcije te iskorištenja fotoprodukata, zaključilo se kako je protočni reaktor svakako bolji izbor u odnosu na šaržni reaktor.

Abstract (english)

Resveratrol is a stilbenoid polyphenol with various antioxidant, antitumor, neuroprotective and cardioprotective properties, and due to low bioavailability, its biologically active derivatives are being developed. These analogs show significant antioxidant potential and inhibitory activity for the cholinesterase enzyme, which is proven by lower IC50 values compared to standard inhibitor galantamine. In this work, heteroaromatic derivatives of resveratrol were synthesized by the Wittig reaction, which served as starting compounds 1-5 for further photochemical transformations in batch and flow reactors. Photochemical transformations were carried out by direct illumination of the initial compounds at different wavelengths or in the presence of a porphyrin photocatalyst with four different LED lamps. In addition to the wavelength and the photocatalyst, the residence time and temperature also varied in the flow reactor. The results mainly show cyclization products as well as trans-cis isomerization, and computational study of the photoreactivity of the starting compound 1 determined the main paths of their obtaining. Comparing the productivity and selectivity of the reaction and yields of photoproducts, it was concluded that the flow reactor is a better choice compared to the batch reactor.

• Keywords: rezveratrol; heteroaromatski derivati; šaržni reaktor; protočni reaktor; fotokemija; fotokatalizatori
• Keywords (english): resveratrol; heteroaromatic derivatives; batch reactor; flow reactor; photochemistry; photocatalysts
• Language: croatian
• URN:NBN: urn:nbn:hr:149:729418
• Study programme: Title: Chemical Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: sveučilišni/a magistar/magistra inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-11-08 12:38:38