Issue 28, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Jun 2017
Accepted
28 Jun 2017
First published
28 Jun 2017

Org. Biomol. Chem., 2017,15, 6001-6005

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements