Multicomponent Assembly of Bicyclic Aza-peroxides Catalyzed by Samarium Complexes and Their Cytotoxic Activity

An original strategy toward bridged tetraoxazaspirobicycloalkanes was developed. The synthesis is based on a three-component condensation–cyclization reaction of primary arylamines with 1,1′-peroxybis (1-hydroperoxycycloalkanes) and pentane-1,5-dial catalyzed by Sm­(NO3)3·6H2O. The structures and co...

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Veröffentlicht in:Journal of organic chemistry 2023-08, Vol.88 (16), p.11473-11485
Hauptverfasser: Makhmudiyarova, Nataliya N., Ishmukhametova, Irina R., Tyumkina, Tatyana V., Mescheryakova, Ekaterina S., Dzhemileva, Lilya, D’yakonov, Vladimir, Terent’ev, Alexander O., Dzhemilev, Usein M.
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Sprache:eng
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Zusammenfassung:An original strategy toward bridged tetraoxazaspirobicycloalkanes was developed. The synthesis is based on a three-component condensation–cyclization reaction of primary arylamines with 1,1′-peroxybis (1-hydroperoxycycloalkanes) and pentane-1,5-dial catalyzed by Sm­(NO3)3·6H2O. The structures and conformations of the products were determined by X-ray diffraction analysis and 1H and 13C NMR spectroscopy. High cytotoxic activity and biological potential toward ferroptosis induction were found for the synthesized bicyclic aza-peroxides.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00555