Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity.

Abstract

The Sonogashira reaction can be applied for the preparation of acetylenic derivatives of betulonic acid where the triterpenoid moiety can serve as either the halo- or the acetylenic component. This reaction opened access to the first derivatives of betulonic acid containing either the arylethynyl (C[triple bond]C-Ar(Het) or the ethynyl (C[triple bond]CH) moieties. From the fundamental perspective, this work illustrates the possibility of selective Pd-catalyzed cross-coupling at terminal acetylenes in the presence of a terminal alkene. Hepatoprotective and anti-inflammatory properties of selected acetylenic derivatives of betulonic acid were investigated using the CCl4-induced hepatitis and carrageenan-induced edema models, respectively.

DOI: 10.1016/j.bmc.2009.05.059

Cite this paper

@article{Vasilevsky2009EfficientSO, title={Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity.}, author={Sergey F Vasilevsky and Anastasiya I Govdi and El'vira E Shults and Makhmut M. Shakirov and Irina V. Sorokina and Tatyana G. Tolstikova and Dmitry S. Baev and Genrikh A Tolstikov and Igor V. Alabugin}, journal={Bioorganic & medicinal chemistry}, year={2009}, volume={17 14}, pages={5164-9} }