SYNTHESIS AND HEMOLYTIC PROPERTIES OF DERIVATIVES OF 4,4'-DIHYDROXYBIPHENYL – 2,2'-[BIPHENYL-4,4'- DIYLBIS(OXY)]BIS[N-(METHYLAMINO)ALKILACETAMIDES]

Abstract

The purpose of this work was synthesis of 4,4’-dihydroxybiphenyl derivatives, namely 2,2’-[biphenyl-4,4’-diylbis(oxy)]bis[N-(2-aminoalkyl)acetamide], study of their hemolytic properties and the effect of the side chain structure on hemolytic properties. 2,2’-[Biphenyl-4,4’-diylbis(oxy)]diacetic acid was synthesized by alkylation of 4,4’-dihydroxybiphenyl with methylbromoacetate, followed by alkaline hydrolysis. Chloroanhydride was obtained by treatment of this acid with thionyl chloride. 2,2’-[Biphenyl-4,4’-diylbis(oxy)] bis-[N-(2-aminoalkyl)acetamides] were synthesized in the biphasic media (dichloromethane/ aqueous sodium carbonate). Structures of synthesized compounds were proved by mass-spectrometryand 1Н NMR. Hemolytic properties were studied using healthy donors’ erythrocytes 0(I)/Rh+. The absence of hemolytic properties for obtained compounds was shown, unlike similar 4,4’-aminoalkoxybiphenyls for which a significant hemolysis was shown. Thus, replacement of the ethylene group with amide group in the side chain of 4,4’-bissubstituted biphenyls significantly reduces hemolytic properties.

Keywords

• похідні 4,4’-дигідроксибіфенілу
• синтез 2,2’-[біфеніл-4,4’-диілбіс(окси)]біс[N-(ω-аміноалкіл)ацетамідів]
• гемолітичні властивості