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Efficient Synthesis of the First Betulonic Acid-Acetylene Hybrids and Their Hepatoprotective and Anti-Inflammatory Activity

Efficient Synthesis of the First Betulonic Acid-Acetylene Hybrids and Their Hepatoprotective and Anti-Inflammatory Activity

Sergey F Vasilevsky, Anastasiya I Govdi, El'vira E Shults, Makhmut M Shakirov, Irina V Sorokina, Tatyana G Tolstikova, Dmitry S Baev, Genrikh A Tolstikov, Igor V Alabugin

Bioorg Med Chem. 2009 Jul 15;17(14):5164-9.

PMID: 19524443

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4481623	Betulonic acid		4481-62-3	Price

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