prikaz prve stranice dokumenta Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja
Embargo period 2026-09-01
master's thesis
Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2023. urn:nbn:hr:149:926794
Curiš, Doria
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

Curiš, D. (2023). Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:926794

Curiš, Doria. "Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2023. https://urn.nsk.hr/urn:nbn:hr:149:926794

Curiš, Doria. "Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2023. https://urn.nsk.hr/urn:nbn:hr:149:926794

Curiš, D. (2023). 'Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 29 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:926794

Curiš D. Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2023 [cited 2024 November 29] Available at: https://urn.nsk.hr/urn:nbn:hr:149:926794

D. Curiš, "Sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2023. Available at: https://urn.nsk.hr/urn:nbn:hr:149:926794

Metadata
TitleSinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja
Title (english)Synthesis of novel C6-substituted purine derivatives using Pd-catalyzed cross-coupling reactions
AuthorDoria Curiš
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
U ovom radu opisana je sinteza novih C6-supstituiranih purinskih derivata Pd-kataliziranim reakcijama unakrsnog spajanja. N-9 propargilirani derivati purina 1a i 1b priređeni su reakcijom N-alkiliranja. Odgovarajući aldoksim 3 potreban za sintezu izoksazolnih derivata priređen je reakcijom kloriranja piridin-2-aldoksima 2. Novi 2,3-disupstituirani purinski izoksazoli 4a i 4b priređeni su bazno-kataliziranom 1,3-dipolarnom cikloadicijom iz N-9 propargiliranih derivata purina 1a i 1b te kloriranog aldoksima 3. Dobiveni 2,3-disupstituirani purinski izoksazoli 4a i 4b supstituirani su u položaju C-6 uporabom paladij-katalizirane Suzuki-Miyaurine i Sonogashirine reakcije unakrsnog povezivanja. Na taj su način uspješno sintetizirani C6-supstituirani izoksazolni derivati purina 5a, 5b i 6a–d. Nadalje, odabrani C6-supstituirani izoksazolni derivati purina 5a, 5b i 6b korišteni su kao ligandi za sintezu renij(I) trikarbonilnih kompleksa 7a, 7b i 8. Strukture novosintetiziranih spojeva potvrđene su spektroskopijom 1H i 13C NMR te UV/Vis i IR-spektroskopijom. Antitumorska ispitivanja novosintetiziranih spojeva su u tijeku.
Abstract (english)
In this work the synthesis of novel C6-substituted purine derivatives using Pd-catalyzed cross-coupling reactions is described. N-9 propargylated purine derivatives 1a and 1b were prepared by N-alkylation. The corresponding aldoxime 3 for the synthesis of isoxazole derivatives was synthesized by the chlorination reaction of pyridine-2-aldoxime 2. A novel 2,3-disubstituted purine isoxazole derivatives 4a and 4b were prepared by base-catalyzed 1,3-dipolar cycloaddition of N-9 propargylated purine derivatives 1a and 1b and chlorinated oxime 3. Synthesized 2,3-disubstituted purine-isoxazole derivatives 4a and 4b were functionalized at C-6 position using Pd-catalyzed Suzuki-Miyaura and Sonogashira cross-coupling reaction and so C6-substituted purine-isoxazole derivatives 5a, 5b and 6a–d were synthesized. Selected C6-substituted purine-isoxazole derivatives 5a, 5b and 6b were also used as ligands for the synthesis of rhenium(I) tricarbonyl complexes 7a, 7b and 8. The structures of all compounds were determined by 1H NMR and 13C NMR spectroscopy as well as by UV/Vis and IR spectroscopy. Anticancer evaluations of novel compounds are in progress.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:926794
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: Materials Science and Engineering - Graduate study
Study programme type: university
Study level: graduate
Academic / professional title: sveučilišni/a magistar/magistra inženjer/inženjerka kemijskog inženjerstva (sveučilišni/a magistar/magistra inženjer/inženjerka kemijskog inženjerstva)
Type of resourceText
File originBorn digital
Access conditionsEmbargoed access
Embargo expiration date: 2026-09-01
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Created on2023-11-24 11:06:45