Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola

master's thesis

• Title (english): Photochemical synthesis and molecular modeling of new chlorine derivatives of naphthotriazole
• Author: Ingo Borić
• Mentor: Irena Škorić (mentor)
• Mentor: Borislav Kovačević (komentor)
• Committee member: Irena Škorić (predsjednik povjerenstva)
• Committee member: Dragana Vuk (član povjerenstva)
• Committee member: Ljerka Kratofil Krehula (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2024-07-10, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U svrhu proučavanja biološke aktivnosti, specifično inhibicije acetilkolinesteraze (AChE) i butirilkolinesteraze (BChE), sintetizirani su novi derivati naftotriazola 11-15. Sinteza se sastojala od tri koraka. Prvi korak je činila nukleofilna supstitucija, čime su nastali aldehidi 1-5. Nastali aldehidi su u drugom koraku podvrgnuti Wittigovoj reakciji, gdje su kao produkti nastali cis- i trans- izomeri heterostilbena 6-10. U posljednjem koraku, heterostilbeni su podvrgnuti fotokemijskoj ciklizaciji pri čemu su nastali naftotriazoli 11-15, koji literaturno nisu poznati. Naftotriazoli 11-14 uspješno su sintetizirani, dok se naftotriazol 15 pokazao zahtjevnijim za sintezu te nije pronađen uspjeh pri njegovoj sintezi. Novi sintetizirani i izolirani spojevi okarakterizirani su 1D NMR tehnikama. Biološka ispitivanja pokazala su kako naftotriazoli 11-13 posjeduju inhibicijski potencijal prema BChE, dok 12 jedini pokazuje isti i prema AChE te ujedno pokazuje najbolje rezultate pri inhibiciji oba enzima. Elektronska struktura i termodinamička stabilnost sintetiziranih naftotriazola istraživana je računalnim modeliranjem, a s obzirom na rezultate bioloških ispitivanja, naftotriazol 12 računalno je ispitan kao potencijalni inhibitor enzima AChE i BChE.

Abstract (english)

In order to study the biological activity, specifically inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), new naphthotriazole derivatives 11-15 were synthesized. The synthesis consists of three steps. The first step was the nucleophilic substitution, resulting in aldehydes 1-5. The aldehydes were subjected to the Wittig reaction in the second step, where cis- and trans-isomers of heterostilbenes 6-10 were formed as products. In the last step, heterostilbenes were subjected to photochemical cyclization, whereby naphthotriazoles 11-15 were formed, which are not known in the literature. Naphtotriazoles 11-14 were successfully synthesized, while naphthotriazole 15 proved to be more demanding for synthesis and no success was found in its synthesis. New synthesized and isolated compounds were characterized by 1D NMR techniques. Biological tests showed that naphthotriazoles 11-13 possess inhibitory potential towards BChE, while 12 is the only one showing the same activity also towards AChE and at the same time showed the best results in inhibiting both enzymes. The electronic structure and thermodynamic stability of synthesized naphthotriazoles were investigated by computer modeling, and considering the results of biological tests, naphthotriazole 12 was computationally tested as a potential inhibitor of AChE and BChE enzymes.

• Keywords: fotokemijska sinteza; inhibicija AChE i BChE; kolinesteraze; naftotriazoli; računalno modeliranje
• Keywords (english): photochemical synthesis; inhibition of AChE and BChE; cholinesterases; naphthotriazoles; computer modeling
• Language: croatian
• URN:NBN: urn:nbn:hr:149:380437
• Study programme: Title: Applied Chemistry - Graduate 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: graduate; Academic / professional title: sveučilišni/a magistar/magistra primijenjene kemije (sveučilišni/a magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2024-07-15 12:50:24