Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 5, Pages 965-975Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501278
Keywords
Medicinal chemistry; Drug discovery; Anticancer agents; Oxygen heterocycles; Domino reactions; Michael addition; Antioxidants
Categories
Funding
- Fundacao para a Ciencia e a Tecnologia (FCT), Portugal [UID/QUI/00062/2013, UID/CTM/50011/2013]
- European Union (EU)
- Quadro de Referencia Estrategico Nacional (QREN)
- Fundo Europeu de Desenvolvimento Regional (FEDER)
- Programa Operacional Factores de Competitividade (COMPETE)
- Associate Laboratory Centro de Investigacao em Materiais Ceramicos e Compositos - CICECO
- Portuguese National NMR Network (RNRMN)
- European Community [215009]
- General Directorate for Scientific Research and Technological Development-DGRSDT of Algeria
- FCT
- project New Strategies Applied to Neuropathological Disorders - QREN, Mais Centro-Programa Operacional Regional do Centro [CENTRO-07-ST24-FEDER-002034]
- EU, FEDER
- RSL, Luxembourg
- Fondation de Recherche Cancer et Sang
- Recherches Scientifiques Luxembourg association
- Een Haerz fur Kriibskrank Kanner association
- Action Lions Vaincre le Cancer association, Interreg IVA project Corena
- Televie Luxembourg
- Research Institute of Pharmaceutical Sciences by the NRF of the MEST of Korea [GCRC 2012-0001184]
- Brain Korea (BK21) PLUS program
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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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