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In a tandem reaction, organobase\u2010catalysed Michael addition of R<jats:sup>1<\/jats:sup>COCH<jats:sub>2<\/jats:sub>COR<jats:sup>2<\/jats:sup> on chromone\u20103\u2010carboxylic acid led to decarboxylation and pyran\u20104\u2010one ring opening of the latter. This was followed by chromone\u2010 and\/or chromanone ring closure of the resulting Michael adducts when R<jats:sup>1<\/jats:sup> is an <jats:italic>ortho<\/jats:italic>\u2010hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones <jats:bold>3o<\/jats:bold>\u2013<jats:bold>r<\/jats:bold> (2.1\u20133.1 \u00b5mol Trolox equiv.\/\u00b5mol compound in the DPPH assay). Chromanones <jats:bold>3p<\/jats:bold> and <jats:bold>3r<\/jats:bold> and 2\u2010styrylchromone <jats:bold>3k<\/jats:bold> were also most potent in inducing the cytoprotective Keap1\u2010Nrf2 signalling pathway in a reporter gene assay (fivefold induction at concentrations &lt;3 \u00b5<jats:sc>M<\/jats:sc>). Of the seven compounds evaluated for antiproliferative activities, <jats:bold>3k<\/jats:bold> and <jats:bold>3r<\/jats:bold> were the most active, inhibiting leukaemia K562 cell proliferation by 50\u2009% after 72 h at concentrations of 4.5 and 7.9 \u00b5<jats:sc>M<\/jats:sc>, whereas normal peripheral blood mononuclear cells were not affected.<\/jats:p>","DOI":"10.1002\/ejoc.201501278","type":"journal-article","created":{"date-parts":[[2016,1,16]],"date-time":"2016-01-16T16:52:16Z","timestamp":1452963136000},"page":"965-975","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":33,"title":["One\u2010Pot Synthesis of Benzopyran\u20104\u2010ones with Cancer Preventive and Therapeutic Potential"],"prefix":"10.1002","volume":"2016","author":[{"given":"Oualid","family":"Talhi","sequence":"first","affiliation":[]},{"given":"Lidia","family":"Brodziak\u2010Jarosz","sequence":"additional","affiliation":[]},{"given":"Jana","family":"Panning","sequence":"additional","affiliation":[]},{"given":"Barbora","family":"Orlikova","sequence":"additional","affiliation":[]},{"given":"Clemens","family":"Zwergel","sequence":"additional","affiliation":[]},{"given":"Tzvetomira","family":"Tzanova","sequence":"additional","affiliation":[]},{"given":"St\u00e9phanie","family":"Philippot","sequence":"additional","affiliation":[]},{"given":"Diana C. 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