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DOI: 10.1055/s-0030-1258293
Synthesis and Evaluation of Biological Activity of the Quaternary Ammonium Salts of Lupane-, Oleanane-, and Ursane-Type Acids
Publication History
Publication Date:
08 October 2010 (online)
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Abstract
The anticancer properties of the derivatives of natural pentacyclic triterpenoids have received much attention recently. Here we present the preparation and the evaluation of the anticancer activity of a novel group of derivatives: quaternary ammonium esters. The esters were synthesized by quaternization of the respective 2-bromoethyl esters of betulinic, dihydrobetulinic, platanic, oleanolic, ursolic, and 3β-acetoxy-21-oxolup-18-en-28-oic acids with common low-molecular-weight tertiary amines, namely trimethylamine, triethylamine, pyridine, and triethanolamine. However, the desired quaternary salts were obtained only from trimethylamine, triethylamine, and pyridine. In case of the reaction with triethanolamine the elimination of one of the 2-hydroxyethyl groups occurred and only tertiary amines were formed. Most of the prepared compounds showed significant in vitro cytotoxic activity on the CEM T-lymfoblastic leukaemia cell line. Three of the six selected compounds {2-(triethylammonio)ethyl 3β-hydroxylup-20(29)-en-28-oate bromide, 2-(triethylammonio)ethyl 3b-hydroxylupan-28-oate bromide and 2-[bis(2-hydroxyethyl)amino]ethyl 3β-hydroxylupan-28-oate] exhibited strong cytotoxic activity on a panel of ten cell lines, including drug resistant.
Key words
amines - esters - terpenoids - natural products - cytotoxicity screening
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- Supporting Information
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