prikaz prve stranice dokumenta Nove soli tienobenzo-triazola - sinteza i biološka aktivnost
  Download
PDF 2 MB
undergraduate thesis
Nove soli tienobenzo-triazola - sinteza i biološka aktivnost
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2024. urn:nbn:hr:149:684255
Horvat, Tea
University of Zagreb
Faculty of Chemical Engineering and Technology

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

Cite this document

Horvat, T. (2024). Nove soli tienobenzo-triazola - sinteza i biološka aktivnost (Undergraduate thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:684255

Horvat, Tea. "Nove soli tienobenzo-triazola - sinteza i biološka aktivnost." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2024. https://urn.nsk.hr/urn:nbn:hr:149:684255

Horvat, Tea. "Nove soli tienobenzo-triazola - sinteza i biološka aktivnost." Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2024. https://urn.nsk.hr/urn:nbn:hr:149:684255

Horvat, T. (2024). 'Nove soli tienobenzo-triazola - sinteza i biološka aktivnost', Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 20 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:684255

Horvat T. Nove soli tienobenzo-triazola - sinteza i biološka aktivnost [Undergraduate thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2024 [cited 2024 December 20] Available at: https://urn.nsk.hr/urn:nbn:hr:149:684255

T. Horvat, "Nove soli tienobenzo-triazola - sinteza i biološka aktivnost", Undergraduate thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2024. Available at: https://urn.nsk.hr/urn:nbn:hr:149:684255

Metadata
TitleNove soli tienobenzo-triazola - sinteza i biološka aktivnost
Title (english)New methoxy-substituted naphthotriazoles - synthesis and biological activity
AuthorTea Horvat
MentorIrena Škorić (mentor)
Committee memberIrena Škorić (predsjednik povjerenstva)
Committee memberDragana Vuk (član povjerenstva)
Committee memberLidija Furač (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2024-09-13, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
Cilj ovog rada bila je sinteza novih soli tienobenzo-triazola s potencijalnom biološkom aktivnošću. Tijek sinteze praćen je nizom od četiri uzastopne reakcije. Prvim stupnjem dobivaju se različiti derivati triazolnih aldehida reakcijom 1-(4-nitrofenil)-1H-1,2,3-triazol-4-karbaldehida, prethodno pripremljenog u našem laboratoriju, i odgovarajućeg amina. Nadalje slijedi Wittigova reakcija, općenito poznata kao reakcija dobivanja alkena. Takvom reakcijom aldehidi reagiraju s fosforovim ilidom čime se dobivaju smjese izomera triazolnih tienostilbena. Spomenuti produkti su zbog nastanka konjugiranog sustava uspješno podvrgnuti fotokemijskim reakcijama čime dolazi do ciklizacije odnosno zatvaranja prstena i sinteze tienobenzo-triazola. Posljednjim stupnjem dodatkom alkil-halogenida dobivaju se triazolne soli koje su testirane na biološku aktivnost, prvenstveno kao potencijalni inhibitori enzima kolinesteraza. Na temelju rezultata bioloških mjerenja, spoj 6 pokazuje inhibiciju enzima butirilkolinesteraze s vrijednosti IC50 od 24,3 μM dok njegova sol 10 čak IC50 od 1,83 μM, što je nekoliko puta bolja inhibicijska aktivnost od one koju pokazuje standardni reverzibilni inhibitor galantamin.
Abstract (english)
The aim of this work was the synthesis of new thienobenzotriazole salts with potential biological activity. The course of the synthesis is followed by a series of four consecutive reactions. In the first stage, various derivates of triazole aldehydes are obtained by the reaction of 1-(4-(nitrophenyl)-1H-1,2,3-triazole-4-carbaldehyde, previously prepared in out laboratory, and the corresponding amine. Further follows the Wittig reaction, generally known as the alkene formation reaction. The aldehydes react with phosphorus ylide, resulting in mixtures of triazole-thienostilbene isomers. Due to the formation of a conjugated system, the mentioned products are succesfully subjected to photochemical reactions, which leads to cyclization, i.e. ring closure and synthesis of thienobenzo-triazoles. The last step is the addition of alkyl halide to obtain triazole salts that have been tested for biological activity, as potential cholinesterase enzyme inhibitor. Based on the results of biological measurements, compound 6 shows inhibition of the butyrylcholinesterase enzyme with an IC50 value of 24,3 μM, while its salt 10 even has an IC50 of 1,83 μM, which is several times better inhibitory activity than that shown by the standard reversible inhibitor galantamine.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:684255
Study programmeTitle: 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 resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Created on2024-11-14 14:36:27