Primjena protočnih mili- i mikroreaktora u sintezi heterocikličkih analoga rezveratrola

master's thesis

• Title (english): Application of flow mili- and microreactors in the synthesis of heterocyclic resveratrol analogues
• Author: Lucija Rajič
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Anita Šalić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2022-06-13, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Rezveratrol (3,4’,5-trihidroksistilben) je bioaktivni neflavonoidni polifenol koji ima sposobnost zaštite od kardiovaskularnih bolesti i raznih karcinoma, a također ima zaštitnu ulogu kod neurodegenerativnih bolesti poput Alzheimerove i Parkinsonove bolesti. Postoji u geometrijskim izomernim oblicima kao cis- i trans-izomer. trans-izomer je stabilniji i povezan je s biološkim svojstvima i zdravstvenim dobrobitima, ali ovaj oblik izomerizira u cis-izomer kada je izložen vidljivom svjetlu ili UV zračenju. Iz tog razloga postoji stalna potraga za novim heterocikličkim analozima rezveratrola koji imaju ista bioaktivna svojstva kao trans-rezveratrol, ali su manje osjetljivi na svjetlost. U ovom radu je Wittigova reakcija odabrana kao sintetski put za proizvodnju poželjnih analoga rezveratrola. Sintetizirana su četiri različita tienilna analoga (s metoksi ili hidroksi skupinom/skupinama, a utvrđeno je da oni s hidroksi skupinom/skupinama pokazuju učinkovitu aktivnost uklanjanja radikala. Reakcije su provedene u šaržnom reaktoru i intenzificirane u mili- i mikroreaktoru. Rezultati su uspoređeni na temelju konverzije, prinosa, produktivnosti i trans/cis omjera. Slični prinosi i pretvorbe postignuti su u svim reakcijskim sustavima, ali u mnogo kraćem vremenu na mili- i mikroskali u odnosu na šaržni reaktor. S druge strane, najveća produktivnost dobivena je u milireaktoru, što ga čini najboljim sustavom za predložene reakcije za sintezu novih heterocikličkih analoga rezveratrola.

Abstract (english)

Resveratrol (3,4’,5-trihydroxystilbene) is a bioactive non-flavonoid polyphenol that has the ability to protect against cardiovascular disease and various cancers, and also plays a protective role in neurodegenerative diseases such as Alzheimer’s and Parkinson’s. It exists in geometric isomeric forms as cis- and trans-isomers. The trans-form is more stable and has been associated with biological properties and health benefits, but this form isomerizes to the cis-form when exposed to visible light or UV irradiation. For this reason, there is a constant search for new heterocyclic resveratrol analogues that have the same bioactive properties as trans-resveratrol but are less sensitive to light. In this work, the Wittig reaction was chosen as the synthetic route for production of desirable resveratrol analogues. Four different thienyl analogues (with methoxy or hydroxy group(s)) were synthesised and it those with hydroxy group(s) were found to have exhibited effective radical scavenging activity. The reactions were carried out in a batch reactor and intensified in milli- and microreactor. The results were compared based on conversion, yield, productivity and trans/cis ratio. Similar yields and conversions were obtained in all reaction systems, but in much shorter time in the milli- and microscale compared to the batch reactor. On the other hand, the highest productivity was obtained in millireactor, making it the best system for the proposed reactions for the synthesis of new heterocyclic resveratrol analogues.

• Keywords: kontinuirani protok; analozi rezveratrola; mili- i mikroreaktor; intenzifikacija procesa
• Keywords (english): continuous flow; resveratrol analogues; milli – and microreactor; process intensifi-cation
• Language: croatian
• URN:NBN: urn:nbn:hr:149:009219
• Study programme: Title: Materials Science and Engineering - Graduate study; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra inženjer/inženjerka kemijskog inženjerstva (magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2023-02-26 14:55:58