Autor: Zoufaly, P.; Adamek, R.; Trhlikova, Z.; Urban, M.
Název práce v češtině: Syntéza heterocyklických derivátů triterpenů
Název práce v angličtině: Synthesis of Heterocyclic Derivatives of Triterpenes
Klíčová slova v češtině: triterpeny, heterocykly, betulinová kyselina, oleanolová kyselina
Klíčová slova v angličtině:triterpenes, heterocycles, betulinic acid, oleanolic acid
Abstrakt česky: Byly syntetizovány série pyridinových, triazolových a thiazolovách heterocyklických derivátů odvozených od kyseliny betulinové, ursolové, oleanolové a jejich cytotoxická aktivita je v současné době zkoumána.
Abstrakt anglicky: Triterpenes are compounds that may be isolated from plants, fungi, bacteria, or marine organisms and a lot of them have various biological activities. Despite that, their use as therapeutics is rather limited by inappropriate pharmacological properties and IC50 in higher micromolar ranges. Very promising derivatives of high cytotoxicity synthesised in our group are triterpenes containing various heterocycles.1 In this work, triterpenes were connected to a small set of aromatic derivatives using Huisgen cycloadition and this way, triazole ring was introduced to the terpenoid moiety. First, molecule 1 was oxidized and alcylated to give propargylester 2 and this compound was subjected to reaction with aromatic azides to give compounds of general formula 3. Another goal was to connect the aromatic heterocyclic ring directly to the A-ring of the terpenic skeleton. From 3-oxotriterpenes, a set of thiazoles (gen. formula 4) and pyridines (gen. formula 5) was prepared. Various terpenes were used and 25 new derivatives were synthesised that are currently being evaluated for their in vitro cytotoxic activity on six cancer cell lines of various histogenetic origin.
Jazyk v originále: Anglický
Publikace abstraktu: Sborník, 159/166
Forma prezentace: Poster
Název konference: Advances in Organic, Bioorganic and Pharmaceutical Chemistry „Liblice 2015“
Místo konání: Olomouc (Czech Republic)
Datum konání: November 6-8
Rok konání: 2015
Způsob financování: GACR (Reg. No.15-05620S)