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

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35 Citations (Scopus)

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 (S{cyrillic}{triple bond, long}S{cyrillic}-Ar(Het) or the ethynyl (S{cyrillic}{triple bond, long}S{cyrillic}N{cyrillic}) 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.

Original languageEnglish
Pages (from-to)5164-5169
Number of pages6
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number14
DOIs
Publication statusPublished - 15 Jul 2009
Externally publishedYes

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Keywords

  • Anti-inflammatory activity
  • Arylacetylenes
  • Betulonic acid
  • Cross-coupling
  • Hepatoprotection
  • Triterpenoids

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Vasilevsky, S. F., Govdi, A. I., Shults, E. E., Shakirov, M. M., Sorokina, I. V., Tolstikova, T. G., Baev, D. S., Tolstikov, G. A., & Alabugin, I. V. (2009). Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity. Bioorganic and Medicinal Chemistry, 17(14), 5164-5169. https://doi.org/10.1016/j.bmc.2009.05.059