Autor: Pokorný, J., Šidová, V., Zoufalý, P., Džubák, P., Hajdúch, M., Urban, M.
Název práce v češtině: Cytotoxicky aktivní konjugáty triterpenů a substituovaných triazolů připravených pomocí 1,3-dipolární Huisgenovy cykloadice
Název práce v angličtině: Cytotoxic Conjugates of Triterpenes and Substituted Triazoles Prepared by Huisgen 1,3-dipolar Cycloaddition
Klíčová slova v češtině: heterocykly, triterpeny, cytotoxicita, mechanizmus účinku
Klíčová slova v angličtině:triterpenes, heterocycles, cytotoxicity, mechanism of action
Abstrakt česky: Byly připraveny tři odlišné série konjugátů triterpenů se substituovaným triazolovým kruhem a následně byla zkoumána jejich cytotoxická aktivita.
Abstrakt anglicky: Pentacyclic triterpenes represent a large group of natural compounds with many interesting biological activities such as anticancer, anti-HIV, antiviral, and others. They have been studied for several decades and a number of modification has been made to improve their activity and pharmacological properties such as solubility in water. Introduction of polar substituents to the active triterpenoid molecule improves the bioavailability, while the biological activity retains or increases in comparison to the parent compound. Here we describe the synthesis and biological evaluation of new triterpenic conjugates containing triazole ring that were prepared via Huisgen 1,3-dipolar cycloaddition. Started with protected betulinic acid (BA), the first step is bromination at allylic position C-30 followed by substitution with sodium azide. The 30-azidoderivative was then subjected to Huisgen CuI catalyzed cycloaddition with various alkynes to give the final conjugates 9, 10 and 11. In the second series, protected terpene is oxidized at C-30 by two step procedure to COOH, and then treated with propargyl bromide to give the propargyl ester from which analogous set of triazoles were prepared. All compounds were tested for their biological activity which will be discussed.
Jazyk v originále: Anglický
Publikace abstraktu: sborník 104/150
Forma prezentace: poster
Název konference: 17th Blue Danube Symposium on Heterocyclic Chemistry
Místo konání: Linz (Rakousko)
Datum konání: August 30 – September 2
Rok konání: 2017
Způsob financování: 15-05620S