Autor: Jurčeka, O.; Urban, M.; Gonzalez, G.; Strnad, M.
Název práce v češtině: Syntéza derivátů betulinu modifikovaných v poloze C-30 pomocí cykloadičních reakcí
Název práce v angličtině: Synthesis of betulin derivatives modified at the position C-30 using cycloaddition reactions
Klíčová slova v češtině: Triterpeny, betulin, cykloadiční reakce
Klíčová slova v angličtině:Triterpenes, betulin, cycloaddition reactions
Abstrakt česky: Byly připraveny série derivátů betulinu s rozličnými substituenty v poloze C-30 s využitím cykloadičních reakcí. Nové molekuly byly podrobeny studiu biologických aktivit.
Abstrakt anglicky: Pentacyclic triterpenoids are secondary metabolites from living organisms such as plants and fungi. They can serve as repellents or in general as antifeedants. These compounds have been intensively studied as potential source of pharmaceutically relevant substances. Many of them have a large variety of biological activities such as selective cytotoxicity in cancer cells, antimalaritical, hepatoprotective.
Our research group is oriented towards the synthesis and development of compounds with anticancer and more recently with neuroprotective activity. The presented work is focused on neuroprotective analogues of betulin 1 prepared by the modification of the position C-30 (Scheme 1). First of all, propargyl ester 2 was prepared by the catalytic hydrogenation of the double bond in betulin 1 followed by the allylic oxidation and alkylation with propargyl bromide. In the next step, Huisgen 1,3-dipolar cycloaddition with organic azides was used to prepare 1,2,3-triazole derivatives 3. Based on the evaluation of the structure-activity relationships during our earlier research7, we selected mainly heterocyclic and sugar substituents. This As a result, a library of 24 new triazole conjugates and several intermediates was obtained. Detailed synthetic procedures and results of biological activities will be discussed.
Jazyk v originále: Anglický
Publikace abstraktu: Sborník 128/204
Forma prezentace: Poster
Název konference: 56th Advances in Organic, Bioorganic, and Pharmaceutical Chemistry Liblice 2022
Místo konání: Špindlerův Mlýn
Datum konání: November 10 – 12
Rok konání: 2022
Způsob financování: 21-00902S, NV19-03-00107, IGA_PrF_2021_024