First synthesis of merged hybrids phosphorylated azirino[2,1-b]benzo[e][1,3]oxazine derivatives as anticancer agents

Eur J Med Chem. 2020 Jan 1:185:111771. doi: 10.1016/j.ejmech.2019.111771.

Victor Carramiñana ¹, Ana M Ochoa de Retana ¹, Jesús M de Los Santos ², Francisco Palacios ³

Affiliations

1 Department of Organic Chemistry I, Faculty of Pharmacy and Lascaray Research Center, University of the Basque Country (UPV/EHU), Paseo de la Universidad 7, 01006, Vitoria, Spain.
2 Department of Organic Chemistry I, Faculty of Pharmacy and Lascaray Research Center, University of the Basque Country (UPV/EHU), Paseo de la Universidad 7, 01006, Vitoria, Spain. Electronic address: jesus.delossantos@ehu.eus.
3 Department of Organic Chemistry I, Faculty of Pharmacy and Lascaray Research Center, University of the Basque Country (UPV/EHU), Paseo de la Universidad 7, 01006, Vitoria, Spain. Electronic address: francisco.palacios@ehu.eus.

PMID: 31671309 DOI: 10.1016/j.ejmech.2019.111771

Abstract

This work describes a straightforward diastereoselective synthetic access to azirino[2,1-b]benzo[e][1,3]oxazines containing phosphorus substituents such as phosphonate or phosphine oxide, by means of nucleophilic addition of functionalized Phenols to the C-N double bond of 2H-azirine derivatives. In addition, the cytotoxic effect on cell lines derived from human lung adenocarcinoma (A549) and human embryonic kidney (HEK293) was also screened. Some azirino[2,1-b]benzo[e][1,3]oxazines 4 and 6 exhibited very good activity against the A549 cell line in vitro. Furthermore, selectivity towards Cancer cell (A549) over (HEK293), and non-malignant cells (MCR-5) has been detected.

Keywords

2H-azirines; Antiproliferative effect; Aziridines; Merged hybrid compounds; Phosphorus substituted azirino[2,1-b]benzo[e][1,3]oxazines.

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