Fluorine-containing lupane triterpenoid acid derivatives: Design, synthesis and biological evaluation as potential anti-inflammatory agents

Fluorine-containing lupane triterpenoid acid derivatives: Design, synthesis and biological evaluation as potential anti-inflammatory agents Full article

Journal

Steroids
ISSN: 0039-128X , E-ISSN: 1878-5867

Output data

Year: 2019, Volume: 147, Pages: 62-69 Pages count : 8 DOI: 10.1016/j.steroids.2018.10.001

Tags

Betulonic acid; Betulinic acid; Fluorine-containing amides; Triterpenoid-2-(fluoroacyl)cyclopentane-1,3-dione hybrids; Anti-inflammatory activity; Antioxidant activity

Authors

Khlebnicova Tatyana S. ¹ , Piven Yuri A. ¹ , Baranovsky Alexander V. ¹ , Lakhvich Fedor A. ¹ , Sorokina Iryna V. ² , Tolstikova Tatyana G. ²

Affiliations

1	(Данные Web of science) Natl Acad Sci Belarus, Inst Bioorgan Chem, Acad Kuprevicha Str 5-2, Minsk 220141, BELARUS
2	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Acad Lavrentev Ave 9, Novosibirsk 630090, Russia

A series of novel fluorine-containing lupane triterpenoid acid derivatives with fluoroaromatic amide moieties at the C-28 position (1-8) or with 2-(fluoroacyl) cyclopentane-1,3-dione fragments at the C-3 position (9-18) of lupane skeleton was synthesized. A simple synthesis of novel lupane triterpenoid hybrids with 2-(fluoroacyl)-2-cyclopenten-1-one moieties was developed. An interaction of 2-acyl-3-chlorocyclopent-2-en-1-ones, obtained from corresponding cyclic beta-triketones, with methyl 3-amino-3-deoxybetulinate gave 3 beta-isomers (9-13) and 3 alpha-isomers (14-18) of target hybrids, which were isolated as individual compounds. Anti-inflammatory properties of selected synthesized compounds were studied in vivo using the histamine-, concanavalin A- and sheep erythrocytes immunization-induced mouse paw edema models. The antioxidant activity was investigated in vivo on the model of tetracycline-induced hepatitis. Majority of synthesized fluorine-containing lupane triterpenoid acid derivatives exhibited significant anti-inflammatory and antioxidant effects. Among studied compounds, 3 beta-hybrid 11 with 2-perfluorobutanoyl-2-cyclopenten-1-one moiety was the most potent bioactive compound.

Khlebnicova T.S. , Piven Y.A. , Baranovsky A.V. , Lakhvich F.A. , Sorokina I.V. , Tolstikova T.G.
Fluorine-containing lupane triterpenoid acid derivatives: Design, synthesis and biological evaluation as potential anti-inflammatory agents
Steroids. 2019. V.147. P.62-69. DOI: 10.1016/j.steroids.2018.10.001 WOS Scopus РИНЦ OpenAlex

Published print:

Jul 1, 2019

Web of science:	WOS:000487004300011
Scopus:	2-s2.0-85054438144
Elibrary:	38618215
OpenAlex:	W2895763989

DB	Citing
Web of science	10
Scopus	10
Elibrary	10
OpenAlex	14