Horner–Wadsworth–Emmons approach to piperlongumine analogues with potent anti-cancer activity. Issue 31 (22nd July 2016)

• Record Type: Journal Article
• Authors: Han, Li-Chen; Stanley, Paul A.; Wood, Paul J.; Sharma, Pallavi; Kuruppu, Anchala I.; Bradshaw, Tracey D.; Moses, John E.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 31(2016)
• Page Start: 7585
• Page End: 7593
• Publication Date: 2016-07-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob01160h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Horner–Wadsworth–Emmons approach to a selection of piperlongumine-like compounds from a novel phosphonoacetamide reagent. 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.