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

Han, L. C., Stanley, P. A., Wood, P. J., Sharma, P., Kuruppu, A. I., Bradshaw, T. D., Moses, J. E. (August 2016) Horner-Wadsworth-Emmons approach to piperlongumine analogues with potent anti-cancer activity. Org Biomol Chem, 14 (31). pp. 7585-93. ISSN 1477-0520

URL: https://pubmed.ncbi.nlm.nih.gov/27443386/
DOI: 10.1039/c6ob01160h


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.

Item Type: Paper
Additional Information: Organic & biomolecular chemistry
CSHL Authors:
Communities: CSHL labs > Moses lab
Depositing User: Matthew Dunn
Date: 21 August 2016
Date Deposited: 08 Jan 2021 18:34
Last Modified: 08 Jan 2021 18:34
URI: https://repository.cshl.edu/id/eprint/39566

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