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

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 compoun...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (31), p.7585-7593
Main Authors: Han, Li-Chen, Stanley, Paul A, Wood, Paul J, Sharma, Pallavi, Kuruppu, Anchala I, Bradshaw, Tracey D, Moses, John E
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Line, Tumor
Cell Proliferation - drug effects
Dioxolanes - chemical synthesis
Dioxolanes - chemistry
Dioxolanes - pharmacology
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Reactive Oxygen Species - metabolism
Structure-Activity Relationship
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Summary: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. Horner-Wadsworth-Emmons approach to a selection of piperlongumine-like compounds from a novel phosphonoacetamide reagent.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob01160h