One-Pot Synthesis of Benzopyran-4-ones with Cancer Preventive and Therapeutic Potential
Oualid Talhi*, Lidia Brodziak-Jarosz, Jana Panning, Barbora Orlikova, Clemens Zwergel, Tzvetomira Tzanova, Stéphanie Philippot, Diana C. G. A. Pinto, Filipe A. Almeida Paz, Clarissa Gerhäuser, Tobias P. Dick, Claus Jacob, Marc Diederich, Denyse Bagrel, Gilbert Kirsch and Artur M. S. Silva*
Feb 2016
European Journal of Organic Chemistry
Abstract : 

A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of R1COCH2COR2 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 R1 is an ortho-hydroxyaryl group. Antioxidant testing of 14 derivatives identified strong antiradical properties of chromanones 3or (2.1–3.1 µmol Trolox equiv./µmol 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 µm). Of the seven compounds evaluated for antiproliferative activities, 3k and 3rwere the most active, inhibiting leukaemia K562 cell proliferation by 50 % after 72 h at concentrations of 4.5 and 7.9 µm, whereas normal peripheral blood mononuclear cells were not affected.


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