Search

An efficient method for the synthesis of benzannelated macrocyclic di- and triperoxides by cyclocondensation of phenol, catechol, resorcinol or hydroquinone with bis-hydroperoxides and formaldehyde in the presence of lanthanide catalysts has been developed. Additionally, by using flow cytometry, it has been shown for the first time in this work that thus-synthesized macrocyclic di- and triperoxides are efficient apoptosis inducers in the tumor cultures Jurkat, K562 and U937 and in fibroblasts.

An efficient procedure has been developed for the synthesis of N-substituted tetra(hexa)oxazaspiroalkanes by reaction of heptaoxadispiroalkanes and pentaoxaspiroalkanes with amino acids (glycine, alanine, leucine, valine, methionine) in the presence of samarium-containing catalysts.

An efficient method has been developed for the synthesis of di(tri)peroxysilacycloalkanes by cyclization of geminal bis-hydroperoxides and 1,1′-peroxybis(1-hydroperoxycycloalkanes) with bis(methoxymethyl)diphenylsilane in the presence of lanthanide catalysts. Conditions have been found for the reduction of diphenylhexaoxasiladispirocycloalkanes to diphenyltetraoxasiladispirocycloalkanes.

A promising method for the synthesis of a new class of macrocyclic phosphorus-containing tri- and diperoxides was developed. The method is based on catalytic ring transformation reactions of heptaoxadispiroalkanes, pentaoxacanes, and pentaoxadispiroalkanes with phenylphosphine followed by oxidation of the reaction mixture with H2O2.

An efficient method has been developed for the synthesis of N-aryl(alkyl)-N-(hexaoxazadispiroalkanyl)amines by the reaction of 3,6-di(spiroalkanyl)-substituted heptaoxacycloundecanes with hydrazine derivatives (3-chlorophenylhydrazine, phenylhydrazine, 2,4-dinitrophenylhydrazine, and tert-butylhydrazine) with Sm-containing catalysts. It was found that amines with macrocyclic spiro-linked azatriperoxide substituents exhibit a high cytotoxic activity against Jurkat, K562, and U937 tumor cell line and normal fibroblast cell line.

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.

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.