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

A one-pot synthesis of novel benzopyran-4-ones is described. In a tandem reaction, organobase-catalysed Michael addition of RCOCH2COR on chromone-3-carboxylic acid led to decarboxylation and pyran-4-one ring opening of the latter. This was followed by chromoneand/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 3o–r (2.1– 3.1 μmol Trolox equiv./μmol compound in the DPPH assay).