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 Full article

Journal

Bioorganic and Medicinal Chemistry
ISSN: 0968-0896 , E-ISSN: 1464-3391

Output data

Year: 2009, Volume: 17, Number: 14, Pages: 5164-5169 Pages count : DOI: 10.1016/j.bmc.2009.05.059

Tags

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

Authors

Vasilevsky Sergey F. ¹ , Govdi Anastasiya I. ¹ , Shults El'vira E. ² , Shakirov Makhmut M. ² , Sorokina Irina V. ² , Tolstikova Tatyana G. ² , Baev Dmitry S. ² , Tolstikov Genrikh A. ² , Alabugin Igor V. ³

Affiliations

1	(Данные Web of science) Russian Acad Sci, Inst Chem Kinet & Combust, Siberian Branch, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
3	(Данные Web of science) Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA

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 equivalent to C-Ar(Het) or the ethynyl (C equivalent to 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. (C) 2009 Elsevier Ltd. All rights reserved.

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.
Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity
Bioorganic and Medicinal Chemistry. 2009. V.17. N14. P.5164-5169. DOI: 10.1016/j.bmc.2009.05.059 WOS Scopus РИНЦ

Published print:

Jul 1, 2009

Web of science	WOS:000267873000037
Scopus	2-s2.0-67650178255
Elibrary	13604783
OpenAlex	W2086099335