Synthesis of novel 2-cyano substituted glycyrrhetinic acid derivatives as inhibitors of cancer cells growth and NO production in LPS-activated J-774 cells

Here we report the synthesis and biological activity of new semi-synthetic derivatives of naturally occurring glycyrrhetinic acid bearing a 2-cyano-3-oxo-1-en moiety in the A-ring and double bonds and carbonyl groups in the C, D and E rings. Bioassays using murine macrophage-like and tumor cells sho...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2014-01, Vol.22 (1), p.585-593
Main Authors: Salomatina, Oksana V., Markov, Andrey V., Logashenko, Evgeniya B., Korchagina, Dina V., Zenkova, Marina A., Salakhutdinov, Nariman F., Vlassov, Valentin V., Tolstikov, Genrikh A.
Format: Article
Language:English
Subjects:
Biological activity
Cell Proliferation
Cytotoxicity
Glycyrrhetinic Acid - analogs & derivatives
Glycyrrhetinic Acid - chemical synthesis
Glycyrrhetinic Acid - chemistry
Glycyrrhetinic acid derivatives
Humans
Lipopolysaccharides
Neoplasms - chemistry
Nitric oxide
Nitric Oxide - antagonists & inhibitors
Nitric Oxide - chemistry
Selectivity index
Structure-Activity Relationship
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Summary:Here we report the synthesis and biological activity of new semi-synthetic derivatives of naturally occurring glycyrrhetinic acid bearing a 2-cyano-3-oxo-1-en moiety in the A-ring and double bonds and carbonyl groups in the C, D and E rings. Bioassays using murine macrophage-like and tumor cells show that compound 4, which differs from Soloxolone methyl by the absence of a 9(11)-double bond in the C-ring, displays anti-inflammatory and inhibitory activities with respect to tumor cells with a high selectivity index value.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2013.10.049