Sinteza, fotokemija i računalno istraživanje elektronske strukture novih 1,2,3-triazolnih heterostilbena (CROSBI ID 789685)
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Podaci o odgovornosti
Vukovinski, Ana ; Barić, Danijela (komentor) ; Škorić, Irena (mentor)
hrvatski
Sinteza, fotokemija i računalno istraživanje elektronske strukture novih 1,2,3-triazolnih heterostilbena
Novi triazolni derivati heterostilbena 1-12 sintetizirani su u svrhu proučavanja biološke aktivnosti s naglaskom na inhibiciju acetil- i butirilkolinesteraza (AChE i BChE), te antitumorsku aktivnost. Prvi korak u sintezi željenih spojeva je Wittigova reakcija, čime nastaju smjese cis- i trans-izomera spojeva 1-6. Nakon izolacije i spektroskopske karakterizacije, spojevi 1-6 podvrgnuti su fotokemijskim ispitivanjima. Provedene su fotolize i reakcije elektrociklizacije, čime su dobiveni elektrociklizacijski produkti 7-12. Reakcije elektrociklizacije provedene su u fotokemijskom reaktoru Rayonet s UV-lampama od 300 nm, s elementarnim jodom kao oksidacijskim sredstvom. Spektroskopska karakterizacija svih novih spojeva 1-12 provedena je pomoću 1D i 2D NMR tehnika, UV- Vis spektroskopijom i spektrometrijom masa. Računalnim modeliranjem istraživana je elektronska struktura dobivenih triazolnih derivata i njihova termodinamička stablinost.
biološka aktivnost; elektrociklizacija; inhibicija kolinesteraza; računalno modeliranje; triazoli; Wittigova reakcija
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engleski
Synthesis, photochemistry and computer research of electronic structure of new 1,2,3-triazole heterostilbene
New triazole derivatives of heterostilbene 1-12 were synthesized for the purpose of studying biological activity, with a focus on the inhibition of acetyl- and butyrylcholinesterases (AChE and BChE), as well as antitumor activity. The first step in the synthesis of the desired compounds involved the Wittig reaction, resulting in mixtures of cis- and trans-isomers of compounds 1-6. After isolation and spectroscopic characterization, compounds 1-6 underwent photochemical investigations. Photolysis and electrocycloaddition reactions were conducted, yielding electrocycloaddition products 7-12. Electrocycloaddition reactions were performed in a Rayonet photochemical reactor with 300 nm UV lamps, using elemental iodine as the oxidizing agent. The spectroscopic characterization of all new compounds 1-12 was carried out using 1D and 2D NMR techniques, UV-Vis spectroscopy, and mass spectrometry. Computational modeling was employed to investigate the electronic structure of the obtained triazole derivatives and their thermodynamic stability.
biological activity ; cholinesterase inhibition; computer modeling; electrocyclization triazoles; Wittig reaction
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Podaci o izdanju
Zagreb:
79
2021.
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