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One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential

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.
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Submitted on : Monday, March 27, 2017 - 4:47:27 PM
Last modification on : Friday, March 26, 2021 - 6:34:01 PM

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Oualid Talhi, Lidia Brodziak-Jarosz, Jana Panning, Barbora Orlikova, Clemens Zwergel, et al.. One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2016, pp.965-975. ⟨10.1002/ejoc.201501278⟩. ⟨hal-01496643⟩

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