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Issue 31, 2016
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Horner–Wadsworth–Emmons approach to piperlongumine analogues with potent anti-cancer activity

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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

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Supplementary files

Article information


Submitted
27 May 2016
Accepted
15 Jul 2016
First published
22 Jul 2016

Org. Biomol. Chem., 2016,14, 7585-7593
Article type
Paper

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

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