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

Результат исследований: Материалы для журналаСтатья

35 Цитирования (Scopus)

Выдержка

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.

Язык оригиналаАнглийский
Страницы (с-по)5164-5169
Число страниц6
ЖурналBioorganic and Medicinal Chemistry
Том17
Номер выпуска14
DOI
СостояниеОпубликовано - 15 июл 2009
Опубликовано для внешнего пользованияДа

Отпечаток

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

ASJC Scopus subject areas

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

Цитировать

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.

В: Bioorganic and Medicinal Chemistry, Том 17, № 14, 15.07.2009, стр. 5164-5169.

Результат исследований: Материалы для журналаСтатья

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, том. 17, № 14, стр. 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. В: Bioorganic and Medicinal Chemistry. 2009 ; Том 17, № 14. стр. 5164-5169.
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AU - Shakirov, Makhmut M.

AU - Sorokina, Irina V.

AU - Tolstikova, Tatyana G.

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AU - Alabugin, Igor V.

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AB - 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.

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