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

Bioorg Med Chem. 2014 Jan 1;22(1):585-93. doi: 10.1016/j.bmc.2013.10.049.

Oksana V Salomatina ¹, Andrey V Markov ², Evgeniya B Logashenko ³, Dina V Korchagina ¹, Marina A Zenkova ², Nariman F Salakhutdinov ¹, Valentin V Vlassov ², Genrikh A Tolstikov ¹

Affiliations

1 N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch Russian Academy of Sciences, 9, Lavrentiev ave., Novosibirsk 630090, Russian Federation.
2 Institute of Chemical Biology and Fundamental Medicine, Siberian Branch Russian Academy of Sciences, 8, Lavrentiev ave., Novosibirsk 630090, Russian Federation.
3 Institute of Chemical Biology and Fundamental Medicine, Siberian Branch Russian Academy of Sciences, 8, Lavrentiev ave., Novosibirsk 630090, Russian Federation. Electronic address: evg_log@niboch.nsc.ru.

PMID: 24268542 DOI: 10.1016/j.bmc.2013.10.049

Abstract

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.

Keywords

Biological activity; Cytotoxicity; Glycyrrhetinic acid derivatives; Nitric oxide; Selectivity index.

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