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http://hdl.handle.net/10773/19297
Title: | One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential |
Author: | Talhi, Oualid Brodziak-Jarosz, Lidia Panning, Jana Orlikova, Barbora Zwergel, Clemens Tzanova, Tzvetomira Philippot, Stephanie Pinto, Diana C. G. A. Almeida Paz, Filipe A. Gerhaeuser, Clarissa Dick, Tobias P. Jacob, Claus Diederich, Marc Bagrel, Denyse Kirsch, Gilbert Silva, Artur M. S. |
Keywords: | ANTIOXIDANT ACTIVITY CARCINOMA-CELLS 2-STYRYLCHROMONES FLAVONOIDS CHROMONES AGENTS CYTOTOXICITY DERIVATIVES XANTHOHUMOL SCAVENGERS |
Issue Date: | 2016 |
Publisher: | WILEY-V C H VERLAG GMBH |
Abstract: | A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of (RCOCH2COR2)-C-1 on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromone- and/or chromanone ring closure of the resulting Michael adducts when R-1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3o-r (2.1-3.1 mu mol Trolox equiv./mu mol compound in the DPPH assay). Chromanones 3p and 3r and 2-styrylchromone 3k were also most potent in inducing the cytoprotective Keap1-Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations <3 mu M). Of the seven compounds evaluated for antiproliferative activities, 3k and 3r were the most active, inhibiting leukaemia K562 cell proliferation by 50% after 72 h at concentrations of 4.5 and 7.9 mu M, whereas normal peripheral blood mononuclear cells were not affected. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/19297 |
DOI: | 10.1002/ejoc.201501278 |
ISSN: | 1434-193X |
Publisher Version: | 10.1002/ejoc.201501278 |
Appears in Collections: | CICECO - Artigos |
Files in This Item:
File | Description | Size | Format | |
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One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential_10.1002ejoc.201501278.pdf | 1.26 MB | Adobe PDF |
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