Synthesis and cytotoxicity of lupane-type triterpenoid glyceryl esters

A new series of betulinic acid and betulin derivatives were synthesized by introducing a d-glycerol moiety at the C-3 and/or C-28 positions of the lupane skeleton. The resulting glyceryl esters were evaluated in vitro for their cytotoxic activity against A549, DLD-1 and WS1 human cell lines. The str...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2012-07, Vol.22 (14), p.4735-4739
Main Authors: Thibeault, Dominic, Gauthier, Charles, Legault, Jean, Bouchard, Jimmy, Gagné, Louis, Pichette, André
Format: Article
Language:English
Subjects:
Anticancer
Betulin
Betulinic acid
Biological and medical sciences
Catalysis
Cell Line
Cell Survival - drug effects
Chemical Sciences
Cytotoxicity
esters
Esters - chemical synthesis
Esters - metabolism
glycerol
Glycerol - chemistry
Glyceryl esters
human cell lines
Humans
Lupane
Medical sciences
Molecular Structure
Organic chemistry
Other
Pharmacology. Drug treatments
Structure-Activity Relationship
structure-activity relationships
Triterpenes
Triterpenes - chemistry
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Summary:A new series of betulinic acid and betulin derivatives were synthesized by introducing a d-glycerol moiety at the C-3 and/or C-28 positions of the lupane skeleton. The resulting glyceryl esters were evaluated in vitro for their cytotoxic activity against A549, DLD-1 and WS1 human cell lines. The structure–activity relationships study revealed that the incorporation of a glycerol unit at the C-3 or C-28 position of the lupane core resulted in compounds exhibiting potent cytotoxic activity together with decreased liposolubility.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.05.073