Autor: Pokorný, J., Šidová, V., Zoufalý, P., Džubák, P., Hajdúch, M., Urban, M.
Název práce v češtině: Zavádění polárních substituentů do molekuly triterpenu pomocí Huisgenovy 1,3-dipolární cykloadice
Název práce v angličtině: Introduction of Polar Substituents to the Triterpenes 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 are natural compounds that have many interesting biological activities (anticancer, anti-HIV, antiviral) including high and selective cytotoxicity on cancer cells. These substances have been studied and modified in the past to improve their activity or pharmacological profile. Introduction of polar substituents to the triterpenoid molecules is supposed to improve their solubility in water that is important for their bioavailability. In this work, betulinic acid (1) was firstly protected at the position 3, then brominated at the allylic position 30. Following substitution with sodium azide provided azidoderivatives 6 and 7 that were subjected to Huisgen CuI catalyzed cycloaddition with various aromatic alkynes. Final conjugates 9–11 (Scheme 1) were tested in vitro for their cytotoxic activity on eight tumor cell lines and two fibroblasts. In another series, analogous set of derivatives containing a triazole ring bound by an ester or amide bond to the triterpenic skeleton at the position C-30 was prepared. The cytotoxicity of the majority of the new derivatives retained or increased in comparison to the parent compounds. Synthesis and biological evaluation of this new class of triterpenic conjugates containing a triazole ring will be discussed.
Jazyk v originále: Anglický
Publikace abstraktu: sborník 107/138
Forma prezentace: poster
Název konference: 52nd Advances in Organic, Bioorganic, and Pharmaceutical Chemistry “Liblice 2017”
Místo konání: Lázně Bělohrad (Czech Republic)
Datum konání: November 3 – 5
Rok konání: 2017
Způsob financování: 15-05620S