Triterpenoids are a large group of natural compounds that are found in numerous living organisms, and are particularly prevalent in plants. They often have a variety of biological activities.1 Betulinic acid 1b, for example, has strong anti-HIV and anti-cancer activities. Synthesis of various lupane and 18α-oleanane derivatives will be described including those with a heterocycle condensed to the skeleton, fluoroderivatives, and triterpenes substituted in the position 2. We extracted betulin 1a and betulinic acid 1b from birch and sycamore bark and then we prepared precursors 2 - 5; their condensation with ethylenediamine, hydrazine, hydroxylamine, or thiourea yielded a set of heterocycles2, 3 (e.g. 6-11); their fluorination gave a set of fluoroderivatives.4 Finally, a series of C-2 substituted triterpenes (e.g. 12-14) was obtained by nucleophilic substitution of bromoketone 5. The in vitro cytotoxicity of all compounds prepared in this study was screened on CCRF-CEM cell line, the most active derivatives were tested on a panel of seven cancer cell lines with/without MDR phenotype and non-tumor MRC-5 and BJ fibroblasts. Basic assumptions about structure-activity relationships and possible pharmacophores will be discussed. Acknowledgments This work was supported by the European Social Fund (project CZ.1.07/2.2.00/28.0184, 2012-2015 - Biotrend), the infrastructural part (IMTM) was paid from the Operational Program Research and Development for Innovations (project CZ.1.05/2.1.00/01.0030) and NPUII project LO1304. References: 1. Dzubak, P.; Hajduch, M.; Vydra, D.; Hustova, A.; Kvasnica, M.; Biedermann, D.; Markova, L.; Urban, M.; Sarek, J. Nat. Prod. Rep. 2006, 23, 394-411. 2. Urban, M.; Vlk, M.; Dzubak, P.; Hajduch, M.; Sarek, J. Bioorg. Med. Chem. 2012, 20, 3666-3674. 3. Urban, M.; Sarek, J.; Kvasnica, M.; Tislerova, I.; Hajduch, M. J. Nat. Prod. 2007, 70, 523-532. 4. Biedermann, D.; Urban, M.; Budesinsky, M.; Kvasnica, M.; Sarek, J. J. Fluorine Chem. 2013, 148, 30-35.

Triterpenoid derivatives and their biological activities

249th National Meeting (2015)

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