Sinteza i spektroskopska karakterizacija novih tienobenzo-triazola i njihovih soli

undergraduate thesis

• Title (english): Synthesis and spectroscopic characterization of new thienobenzo-triazoles and their salts
• Author: Sara Gregić
• Mentor: Irena Škorić (mentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Lidija Furač (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2024-09-16, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada bio je sintetizirati nove tienobenzo-triazole, odnosno njihove soli,
s potencijalnim inhibicijskim djelovanjem prema enzimima kolinesterazama. Kao metoda sinteze za tieno-triazolne stilbene korištena je Wittigova reakcija, koja se obično koristi za dobivanje alkena reakcijom aldehida ili ketona s fosforovim ilidom. U ovom slučaju, različiti
1-supstituirani 4-formil-1,2,3-triazoli reagirali su s odgovarajućim fosforovim ilidom kako bi nastali 1,2,3-triazolni stilbeni. Zbog prisutnosti konjugiranog sustava u ovim produktima, oni su uspješno bili podvrgnuti fotokemijskim reakcijama. Prilikom osvjetljavanja stilbenskih derivata došlo je do ciklizacije, odnosno formiranja prstena. Dobiveni produkti, tj. njihova struktura potvrđena je NMR spektroskopijom i masenom spektrometrijom. Biološka ispitivanja pokazala su da spoj 9 pokazuje inhibiciju enzima butirilkolinesteraze s IC50 vrijednosti od 34,6 μM dok njegova sol 13 ima IC50 od 0,6 μM, što je čak deset puta bolja inhibicijska aktivnost od one koju pokazuje standardni reverzibilni inhibitor galantamin.

Abstract (english)

The aim of this study was to synthesize new thienobenzo-triazoles, specifically their salts, with potential cholinesterase inhibition activity. The synthesis of thieno-triazole stilbenes was achieved using the Wittig reaction, a method commonly employed for the preparation of alkenes, where aldehydes or ketones react with phosphorus ylide. In this case, various
1-substituted 4-formyl-1,2,3-triazoles reacted with the corresponding phosphorus ylide to yield 1,2,3-triazole stilbenes. Due to the presence of a conjugated system in these products, they were successfully subjected to photochemical reactions. Upon irradiation of stilbene derivatives, cyclization occurred, leading to ring closure. The structure of the obtained products was confirmed by NMR spectroscopy and mass spectrometry. Biological tests showed that compound 9 shows inhibition of the butyrylcholinesterase enzyme with an IC50 value of 34.6 μM, while its salt 13 has an IC50 of 0.6 μM, which is even ten times better inhibitory activity than that shown by the standard reversible inhibitor galantamine.

• Keywords: alkeni; fotokemijske reakcije; inhibicija kolinesteraza; NMR spektroskopija; triazol; triazolna sol; Wittigova reakcija
• Keywords (english): alkenes; photochemical reactions; cholinesterase inhibition; NMR spectroscopy; triazole; triazolium salt; Wittig reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:516321
• 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: 2024-11-15 12:44:30