RESUMO
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.
Assuntos
Antineoplásicos , Peróxidos , Samário , Conformação Molecular , Cristalografia por Raios X , Antineoplásicos/farmacologia , CatáliseRESUMO
Co(OAc)2-catalyzed ring transformation reaction of 10-aryl-7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecanes with α,ω-dithiols (ethane-1,2-, propane-1,3-, butane-1,4-, pentane-1,5-, and hexane-1,6-dithiols, 3,6-dioxaoctane-1,8-dithiol) giving 3-aryl-1,5,3-dithiazacyclanes was studied.
RESUMO
An efficient method for the synthesis of tetraoxathiaspiroalkanes, tetraoxathiocanes, and hexaoxathiadispiroalkanes was developed by reactions of pentaoxacanes, pentaoxaspiroalkanes, and heptaoxadispiroalkanes with hydrogen sulfide in the presence of a catalyst, Sm(NO3)3·6H2O. We found that the synthesized S-containing di- and triperoxides exhibit high cytotoxic activity against Jurkat, K562, U937, and HL60 tumor cultures, and fibroblasts.
Assuntos
Óxidos S-Cíclicos/química , Óxidos S-Cíclicos/síntese química , Catálise , Técnicas de Química Sintética , Estrutura MolecularRESUMO
An efficient method was developed for the synthesis of tetra(spirocycloalkane)-substituted α,ω-di(1,2,4,5,7,8-hexaoxa-10-azacycloundecan-10-yl)alkanes by a ring transformation reaction of 3,6-di(spirocycloalkane)-substituted 1,2,4,5,7,8,10-heptaoxacycloundecanes with α,ω-alkanediamines (1,4-butane-, 1,5-pentane-, 1,7-heptane-, 1,8-octane- and 1,10-decanediamines) catalyzed by Sm(NO3)3/γ-Al2O3. Using flow cytometry, it was shown for the first time that synthesized dimeric azatriperoxides are efficient apoptosis inducers with Jurkat, K562, U937, and Hek296.