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master's thesis
Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2024. urn:nbn:hr:149:380437
Borić, Ingo
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Borić, I. (2024). Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:380437

Borić, Ingo. "Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2024. https://urn.nsk.hr/urn:nbn:hr:149:380437

Borić, Ingo. "Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2024. https://urn.nsk.hr/urn:nbn:hr:149:380437

Borić, I. (2024). 'Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 16 July 2024, https://urn.nsk.hr/urn:nbn:hr:149:380437

Borić I. Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2024 [cited 2024 July 16] Available at: https://urn.nsk.hr/urn:nbn:hr:149:380437

I. Borić, "Fotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2024. Available at: https://urn.nsk.hr/urn:nbn:hr:149:380437

Metadata
TitleFotokemijska sinteza i molekulsko modeliranje novih klorovih derivata naftotriazola
Title (english)Photochemical synthesis and molecular modeling of new chlorine derivatives of naphthotriazole
AuthorIngo Borić
MentorIrena Škorić (mentor)
MentorBorislav Kovačević (komentor)
Committee memberIrena Škorić (predsjednik povjerenstva)
Committee memberDragana Vuk (član povjerenstva)
Committee memberLjerka Kratofil Krehula (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2024-07-10, 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
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:380437
Study programmeTitle: 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 resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2024-07-15 12:50:24