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(NO)·6HO. The structures and conformations of the products were determined by X-ray diffraction analysis and H and C NMR spectroscopy.

Catalyzed ring transformation of cyclic -aryl-azadiperoxides with participation of α,ω-dithiols.

Co(OAc)-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.

How the oxazole fragment influences the conformation of the tetraoxazocane ring in a cyclohexanespiro-3'-(1,2,4,5,7-tetraoxazocane): single-crystal X-ray and theoretical study.

Single crystals of (2S,5R)-2-isopropyl-5-methyl-7-(5-methylisoxazol-3-yl)cyclohexanespiro-3'-(1,2,4,5,7-tetraoxazocane), CHNO, have been studied via X-ray diffraction. The tetraoxazocane ring adopts a boat-chair conformation in the crystalline state, which is due to intramolecular interactions. Conformational analysis of the tetraoxazocane fragment performed at the B3LYP/6-31G(d,2p) level of theory showed that there are three minima on the potential energy surface, one of which corresponds to the conformation realized in the solid state, but not to a global minimum.

Synthesis and anticancer activity novel dimeric azatriperoxides.

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(NO)/γ-AlO. Using flow cytometry, it was shown for the first time that synthesized dimeric azatriperoxides are efficient apoptosis inducers with Jurkat, K562, U937, and Hek296.