Issue 31, 2016

Horner–Wadsworth–Emmons approach to piperlongumine analogues with potent anti-cancer activity

Abstract

Natural products with anti-cancer activity play a vital role in lead and target discovery. We report here the synthesis and biological evaluation of the plant-derived alkaloid, piperlongumine and analogues. Using a Horner–Wadsworth–Emmons coupling approach, a selection of piperlongumine-like compounds were prepared in good overall yield from a novel phosphonoacetamide reagent. A number of the compounds displayed potent anti-cancer activity against colorectal (HCT 116) and ovarian (IGROV-1) carcinoma cell lines, via a mechanism of action which may involve ROS generation. Contrary to previous reports, no selective action in cancer cell (MRC-5) was observed for piperlongumine analogues.

Graphical abstract: Horner–Wadsworth–Emmons approach to piperlongumine analogues with potent anti-cancer activity

Supplementary files

Article information

Article type
Paper
Submitted
27 May 2016
Accepted
15 Jul 2016
First published
22 Jul 2016

Org. Biomol. Chem., 2016,14, 7585-7593

Horner–Wadsworth–Emmons approach to piperlongumine analogues with potent anti-cancer activity

L. Han, P. A. Stanley, P. J. Wood, P. Sharma, A. I. Kuruppu, T. D. Bradshaw and J. E. Moses, Org. Biomol. Chem., 2016, 14, 7585 DOI: 10.1039/C6OB01160H

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