94482-50-5Relevant academic research and scientific papers
Ursolic acid derivatives as potential agents against acanthamoeba Spp
Sifaoui, Ines,Rodríguez-Expósito, Rubén L.,Reyes-Batlle, María,Rizo-Liendo, Aitor,Pi?ero, José E.,Bazzocchi, Isabel L.,Lorenzo-Morales, Jacob,Jiménez, Ignacio A.
, (2019)
The current chemotherapy of Acanthamoeba keratitis relies on few drugs with low potential and limited efficacy, for all this there is an urgent need to identify new classes of anti-Acanthamoeba agents. In this regard, natural products play an important role in overcoming the current need and medicinal chemistry of natural products represents an attractive approach for the discovery and development of new agents. Ursolic acid, a natural pentacyclic triterpenoid compound, possesses a broad spectrum of activities including anti-Acanthamoeba. Herein, we report on the development by chemical transformation of an ursolic acid-based series of seven compounds (2-8), one of them reported for the first time. The structure-activity relationship (SAR) analysis of their anti-Acanthamoeba activity revealed that acylation/ether formation or oxidation enhances their biological profile, suggesting that the hydrophobic moiety contributes to activity, presumably by increasing the affinity and/or cell membrane permeability. These ursolic acid derivatives highlight the potential of this source as a good base for the development of novel therapeutic agents against Acanthamoeba infections.
Synthesis of novel 8,14-secoursane derivatives: Key intermediates for the preparation of chiral decalin synthons from ursolic acid
Zhang, Chongnan,Yang, Haijun,Lue, Guangying,Liu, Cailin,Tang, Yun,Liu, Laibao
scheme or table, p. 1026 - 1032 (2012/08/08)
The novel 8,14-secoursatriene derivative 6 was synthesized starting from ursolic acid (1) via methyl esterification of the 17-carboxylic acid group and benzoylation of the 3-hydroxy group (→ 2; Scheme 1), ozone oxidation of the C(12)=C(13) bond (→ 3), dehydrogenation with Br2/HBr (→ 4), enol acetylation of the resulting carbonyl group (→ 5; Scheme 2), and ring-C opening with the aid of UV light (→ 6). Ring-C-opened dienone derivative 7 of ursolic acid was also obtained via selective hydrolysis of 6 (Scheme 2). Both compounds 6 and 7 are key intermediates for the preparation of chiral decalin synthons from ursolic acid.
