Supramolecular inclusion complexes of functionally substituted N-benzylidene-and allylidene-isonicotinohydrazides with oligosaccharides and their properties

Abstract

Supramolecular inclusion complexes of functionally substituted N-benzylideneand allylidene-isonicotinohydrazides with oligosaccharides and their propertiesThis paper presents the results of a study of the synthesis and structural features of supramolecular inclusion complexes of N-benzylidene-and allylidene-isonicotinohydrazides with cyclic oligosaccharides (with βand 2-hydroxypropyl-β-cyclodextrins). The results of studying the synthesis and structural features of supramolecular inclusion complexes of N-benzylidene and allylideneisonicotinohydrazides with cyclic oligosaccharides (β-and 2-hydroxypropyl-β-cyclodextrins) are presented. The structure of the obtained supramolecular inclusion complexes was studied using one-dimensional 1 H, 13 C and DEPT NMR and two-dimensional spectroscopy of COSY ( 1 H-1 H), HMQC ( 1 H-13 C) and TOCSY ( 1 H-1 H). The formation of supramolecular inclusion complexes was established on the basis of changes in the chemical shifts of the NMR of the substrate and receptor atoms. Based on the analysis of spectral data, the proposed schemes of the obtained supramolecular inclusion complexes are presented. It was found that the interaction of the studied hydrazone substrates with cyclodextrins forms inclusion complexes 1:1 and 1:2 with the entry of the substrate molecule into the internal cavity of the receptor. The resulting products are able to dissolve in water or form stable aqueous dispersions. The antiradical effect of the synthesized supramolecular inclusion complexes with respect to the 2,2-diphenyl-1-picrylhydrazide radical was evaluated. Under the conditions of this test system, antiradical activity was detected in the supramolecular complex of N-(diethylamino)benzylidene-isonicotinohydrazide. The concentration of the complex was determined, capable of reducing the optical density of 100 μM of the test system solution by 50 %.