magistrsko delo
Dejan Slapšak (Author), Jurij Svete (Mentor), Jurij Lah (Thesis defence commission member), Uroš Grošelj (Thesis defence commission member)

Abstract

V zadnjih nekaj desetletjih je pomembnost vsestransko uporabnih derivatov pirazolidin-3-onov močno narasla. Pomembni predstavniki omenjene skupine organskih molekul so biciklični-3-pirazolidinoni, ki se zaradi visokih protimikrobnih aktivnosti preučujejo kot potencialni antibiotiki in antimalariki. Na začetku študije smo pripravili nabor derivatov pirazolo[1,2-a]pirazola ter surovim reakcijskim zmesem preverili njihov potencialni inhibitorni učinek na plazmodijski encim dihidroorotat dehidrogenaza. Iz reakcijskih zmesi smo s srednjetlačno tekočinsko kromatografijo (MPLC) izolirali nastale večinske in manjšinske izomere ter ponovili testiranje na tistih izomerih, ki so sestavljali zmesi s povišano aktivnostjo. V drugem delu raziskave smo se posvetili pripravi heterogenih bakrovih katalizatorjev in preučili njihovo učinkovitost pretvorbe na izbrani modelni reakciji [3+2] cikloadicije med azometin iminom in metil propiolatom. Zanimalo nas je predvsem, koliko mase katalizatorja in reakcijskega časa je potrebno zagotoviti za popolno pretvorbo reagentov v cikloadukt ter poleg tega še zmožnost ponovne pretvorbe že uporabljenega katalizatorja. Modelno reakcijo smo z izbiro različno substituiranih fenilnih obročev v strukturah azometin iminov želeli posplošiti na čim večji kemijski prostor. Študijo smo zaključili s sintezami potencialnih fluorescentnih označevalcev bioloških molekul, aktiviranih z N-hidroksisukcinimidno in benzotriazolilno skupino.

Keywords

malarija;protimalarijska zdravila;dihidroorotat dehidrogenaza;biciklični pirazolidinoni;enaminoni;koordinacijske spojine;'klik' kemija;heterogena kataliza;magistrska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.09 - Master's Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [D. Slapšak]
UDC: 547.77.057(043.2)
COBISS: 33518851 Link will open in a new window
Views: 522
Downloads: 124
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Other data

Secondary language: English
Secondary title: Synthesis of derivatives of pyrazolo[1,2-a]pyrazole and their inhibition of dihydroorotate dehydrogenase
Secondary abstract: In the last few decades, the importance of versatile pyrazolidin-3-one derivatives has grown significantly. Important representatives of this group of organic molecules are bicyclic-3-pyrazolidinones, which are studied as potential antibiotics and antimalarials due to their high antimicrobial activity. At the beginning of the study, a set of several crude pyrazolo[1,2-a]pyrazole derivatives were prepared and their potential inhibitory effect on the plasmodic enzyme dihydroorotate dehydrogenase was tested on the resulting reaction mixtures. The major and minor isomers were isolated from the reaction mixtures by medium pressure liquid chromatography (MPLC) and testing was repeated on those isomers that made up the mixture with increased activity. In the second part of the study, we focused on the preparation of heterogeneous copper catalysts and examined their conversion efficiency on a selected [3+2] cycloaddition model reaction between azomethine imine and methyl propiolate. We were mainly interested in the mass of the catalyst and the reaction time required for the complete conversion of the reagents into a cycloaduct, as well as reconversion ability of already used catalyst. We wanted to generalize the model reaction to the largest possible chemical space by selecting differently substituted phenyl rings in the structures of azomethine imines. We concluded our study with the synthesis of potential fluorescent markers of biological molecules activated by the N-hydroxysuccinimidyl and benzotriazolyl groups.
Secondary keywords: malaria;dihydroorotate;antimalarial medications;heterogeneous catalysis;
Type (COBISS): Master's thesis/paper
Study programme: 1000375
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, smer Kemija
Pages: 72 str.
ID: 12036921