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Issue 28, 2017
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Design, synthesis, and biological activity of second-generation synthetic oleanane triterpenoids

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Abstract

We report the synthesis and biological activity of C-24 demethyl CDDO-Me 2 and the C-28 amide derivatives 3 and 4, which are analogues of the anti-inflammatory synthetic triterpenoid bardoxolone methyl (CDDO-Me) 1. Demethylation of the C-24 methyl group was accomplished via “abnormal Beckmann” rearrangement and subsequent ring A reformation. Amides 3 and 4 were found to be potent inhibitors of the production of the inflammatory mediator NO in vitro.

Graphical abstract: Design, synthesis, and biological activity of second-generation synthetic oleanane triterpenoids

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Publication details

The article was received on 12 Jun 2017, accepted on 28 Jun 2017 and first published on 28 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01420A
Citation: Org. Biomol. Chem., 2017,15, 6001-6005
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    Design, synthesis, and biological activity of second-generation synthetic oleanane triterpenoids

    L. Fu, Q. Lin, E. O. Onyango, K. T. Liby, M. B. Sporn and G. W. Gribble, Org. Biomol. Chem., 2017, 15, 6001
    DOI: 10.1039/C7OB01420A

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