Glycoconjugation of Betulin Derivatives Using Copper-Catalyzed 1,3-Dipolar Azido-Alkyne Cycloaddition Reaction and a Preliminary Assay of Cytotoxicity of the Obtained Compounds.

Pentacyclic lupane-type triterpenoids, such as betulin and its synthetic derivatives, display a broad spectrum of biological activity. However, one of the major drawbacks of these compounds as potential therapeutic agents is their high hydrophobicity and low bioavailability. On the other hand, the presence of easily transformable functional groups in the parent structure makes betulin have a high synthetic potential and the ability to form different derivatives.

Triphenylphosphonium Analogues of Betulin and Betulinic Acid with Biological Activity: A Comprehensive Review.

Naturally occurring pentacyclic lupane triterpenoids such as betulin (1) or betulinic acid (2) and their synthetic derivatives display a broad spectrum of biological activities and, therefore, have been the subject of great interest. However, the use of these compounds as potential therapeutic agents is limited by their low bioavailability, high hydrophobicity, and insufficient intracellular accumulation. In this context, research on modifications of the parent structures that will improve their pharmacokinetic properties is particularly important.