174740-40-0Relevant articles and documents
Structure - Activity relationship study of betulinic acid, a novel and selective TGR5 agonist, and its synthetic derivatives: Potential impact in diabetes
Genet, Cédric,Strehle, Axelle,Schmidt, Céline,Boudjelal, Geoffrey,Lobstein, Annelise,Schoonjans, Kristina,Souchet, Michel,Auwerx, Johan,Saladin, Régis,Wagner, Alain
, p. 178 - 190 (2010)
We describe here the biological screening of a collection of natural occurring triterpenoids against the G protein-coupled receptor TGR5, known to be activated by bile acids and which mediates some important cell functions. This work revealed that betulinic (1), oleanolic (2), and ursolic acid (3) exhibited TGR5 agonist activity in a selective manner compared to bile acids, which also activated FXR, the nuclear bile acid receptor. The most potent natural triterpenoid betulinic acid was chosen as a reference compound for an SAR study. Hemisyntheses were performed on the betulinic acid scaffold, and we focused on structural modifications of the C-3 alcohol, the C-17 carboxylic acid, and the C-20 alkene. In particular, structural variations around the C-3 position gave rise to major improvements of potency exemplified with derivatives 18 dia 2 (RG-239) and 19 dia 2. The best derivative was tested in vitro and in vivo, and its biological profile is discussed.
Preparation of amino acid conjugates of betulinic acid with activity against human melanoma
Jeong, Hyeh-Jean,Chai, Hee-Byung,Park, So-Young,Kim, Darrick S. H. L.
, p. 1201 - 1204 (1999)
Betulinic acid has been coupled with a series of amino acids at C-28 carboxylic acid position and the toxicity of the derivatives has been evaluated against cultured human melanoma (MEL-2) and human epidermoid carcinoma of the mouth (KB) cell lines. A number of amino acid conjugates of betulinic acid showed improved water solubility as well as selective cytotoxicity. This investigation demonstrates that amino acid conjugates of betulinic acid can produce potentially important derivatives, which may be developed as antitumor agents.
Derivatives of 3-O-(3',3'-dimethylsuccinyl)-betulinic acid
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, (2013/03/26)
The present invention relates to compounds of the following formula (I): or a pharmaceutically acceptable salt thereof, a stereoisomer or a mixture of stereoisomers in any proportion, in particular a mixture of enantiomers, and particularly a racemate mixture, in which R represents a (C1-C10)alkyl group substituted with one or more, preferably one or two, groups chosen from COOH and NHR1, with R1 representing a hydrogen atom or a -Alk, -C(O)-Alk or -C(O)O-Alk group, Alk representing a (C1-C6)alkyl group, as well as a method for preparing them, and their use as a medicine, notably for treating an infection with a retrovirus such as HIV.