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

Research output: Contribution to journalArticle

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

Fingerprint

Acetylene
Anti-Inflammatory Agents
Derivatives
Alkynes
Carrageenan
Alkenes
Hepatitis
Edema
betulonic acid

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

Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity. / Vasilevsky, Sergey F.; Govdi, Anastasiya I.; Shults, El'vira E.; Shakirov, Makhmut M.; Sorokina, Irina V.; Tolstikova, Tatyana G.; Baev, Dmitry S.; Tolstikov, Genrikh A.; Alabugin, Igor V.

In: Bioorganic and Medicinal Chemistry, Vol. 17, No. 14, 15.07.2009, p. 5164-5169.

Research output: Contribution to journalArticle

Vasilevsky, SF, Govdi, AI, Shults, EE, Shakirov, MM, Sorokina, IV, Tolstikova, TG, Baev, DS, Tolstikov, GA & Alabugin, IV 2009, 'Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity', Bioorganic and Medicinal Chemistry, vol. 17, no. 14, pp. 5164-5169. https://doi.org/10.1016/j.bmc.2009.05.059
Vasilevsky, Sergey F. ; Govdi, Anastasiya I. ; Shults, El'vira E. ; Shakirov, Makhmut M. ; Sorokina, Irina V. ; Tolstikova, Tatyana G. ; Baev, Dmitry S. ; Tolstikov, Genrikh A. ; Alabugin, Igor V. / Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity. In: Bioorganic and Medicinal Chemistry. 2009 ; Vol. 17, No. 14. pp. 5164-5169.
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