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Embargo period 2025-09-01
master's thesis
Sinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2023. urn:nbn:hr:149:032149
Sačer, Leon
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

Sačer, L. (2023). Sinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:032149

Sačer, Leon. "Sinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2023. https://urn.nsk.hr/urn:nbn:hr:149:032149

Sačer, Leon. "Sinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2023. https://urn.nsk.hr/urn:nbn:hr:149:032149

Sačer, L. (2023). 'Sinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 28 December 2024, https://urn.nsk.hr/urn:nbn:hr:149:032149

Sačer L. Sinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2023 [cited 2024 December 28] Available at: https://urn.nsk.hr/urn:nbn:hr:149:032149

L. Sačer, "Sinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2023. Available at: https://urn.nsk.hr/urn:nbn:hr:149:032149

Metadata
TitleSinteza i strukturna karakterizacija novih purinskih bioizostera s potencijalnom biološkom aktivnošću
Title (english)Synthesis and structural characterization of novel purine bioisosteres with potential biological activity
AuthorLeon Sačer
MentorSilvana Raić-Malić (mentor)
Committee memberSilvana Raić-Malić (predsjednik povjerenstva)
Committee memberTatjana Gazivoda Kraljević (član povjerenstva)
Committee memberDanijela Ašperger (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2023-09-28, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Abstract
Purini i purinski bioizosteri važni su spojevi u medicinskoj kemiji zbog njihove uloge u različitim staničnim procesima te njihovog značaja u razvoju lijekova. Njihova fizikalno-kemijska svojstva i širok raspon bioloških aktivnosti kao što je antitumorska i antivirusna aktivnost čine ih bitnim farmakoforima za razvoj lijekova. U ovom radu sintetizirani su izoksazolni derivati purina i 7-deazapurina reakcijom bazno katalizirane 1,3-dipolarne cikloadicije N-propargiliranih heterocikličkih derivata i nitrilnih oksida koji su prethodno pripravljeni in situ iz hidroksimoilnih klorida. Sintetizirani spojevi 33−38 u daljnjem su stupnju modificirani na položaju C-6 purinske jezgre kako bi se vidio utjecaj ovakve kemijske transformacije na biološku aktivnost. Za tu su svrhu provedene Suzuki-Miyaurine i Sonogashirine reakcije katalizirane paladijem koje su potpomognute mikrovalnim zračenjem. Piridinski derivati supstituirani na izoksazolnom prstenu nadalje su korišteni kao ligandi za sintezu renij(I) trikarbonilnih metalnih kompleksa. Ovakvo uvođenje metala u strukturu potencijalno biološki aktivnih spojeva može povoljno utjecati na aktivnost te poboljšati fizikalno-kemijska svojstva nastalih metalnih kompleksa. Svi sintetizirani spojevi i metalni kompleksi strukturno su okarakterizirani pomoću spektroskopije 1H i 13C NMR, UV-Vis i IR, a struktura metalnog kompleksa 35a dodatno je potvrđena rendgenskom strukturnom analizom.
Abstract (english)
Due to their crucial function in numerous biological processes and their usefulness in the development of drugs, purines and purine bioisosteres are significant compounds in medicinal chemistry. Their physicochemical properties and wide range of biological activities, such as antitumor and antiviral activity make them essential pharmacophores for the drug development. In this work, various isoxazole derivatives of purine and 7-deazapurine were synthesized. The target compounds were synthesized by a base-catalyzed 1,3-dipolar cycloaddition reaction between N-propargylated heterocycles and nitrile oxides generated in situ from hydroxymoyl chlorides. The synthesized compounds 33−38 were then modified at the C-6 position of the purine in order to improve biological activity. Suzuki-Miyaura and Sonogashira palladium catalyzed cross-coupling reactions were performed under microwave irradiation. Pyridine-substituted isoxazole derivatives were used subsequently as ligands for the synthesis of rhenium(I) tricarbonyl metal complexes. The introduction of metals into the structure of potentially biologically active compounds can favorably influence the activity and improve the physicochemical properties. All synthesized compounds and metal complexes were structurally characterized using 1H and 13C NMR, UV-Vis and IR spectroscopy, while the structure of metal complex 35a was additionally confirmed by X-ray structural analysis.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:032149
ProjectNumber: IP-2018-01-4682
Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja
Acronym: PurBioCaPa
Leader: Silvana Raić-Malić
Jurisdiction: Croatia
Funder: HRZZ
Funding stream: IP
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 conditionsEmbargoed access
Embargo expiration date: 2025-09-01
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Created on2023-11-24 09:53:01