A series of new derivatives of 1,2,4-triazoles have been synthesized and their antioxidant properties have been studied. It was established that the obtained compounds exhibit a stabilizing effect on cell membranes and demonstrate antioxidant activity with respect to erythrocytes under oxidative stress conditions.
New benzo-substituted 4-(aminophenylamino)-2-methylquinolines, 3-substituted 4-hydroxy(chloro and mercapto)quinolines, and thienoquinolines were synthesized. A model system based on oxidative damage to erythrocyte membranes induced by the combined actions of hydrogen peroxide and ionizing radiation was used to study the antihemolytic effects of these compounds as a means of assessing their antiradical/antioxidant properties. In the absence of x-rays, substances of the 3-substituted 4-hydroxy(chloro and mercapto)quinoline and thienoquinoline series were found to have marked antihemolytic effects, associated with significant influences on the structural stability of erythrocytes. However, with irradiation, the membrane-protecting effects were more marked with benzo-substituted 4-(aminophenylamino)-2-methylquinoline derivatives.
The antioxidant, antiradical, and membranotropic properties of newly synthesized compounds of the group of N-[3-hydroxy-3-(p-substituted phenyl)-1-propyl] amino acids were studied on model systems in vitro. According to the results, amino-acid derivatives of aminopropanols did not exhibit any significant antioxidant or antiradical activity as evidenced by Fe(II)-stimulated ascorbate-dependent peroxidation, by spectrophotometric monitoring of a decrease in the concentration of stable 2,2-diphenyl-1-picrylhydrazyl radical, or by photochemiluminescence techniques. However, these compounds revealed a membrane-stabilizing effect preventing hemolytic destruction of cells under conditions of H 2 O 2 -stimulated oxidative stress of erythrocytes. In this respect, derivatives of glycine, leucine, and methionine were most interesting.
In vitro model systems were used to study the antioxidant and membrane-stabilizing properties of 1-(4-substituted phenyl)-2H-(phenyl)-3-aminopropan-1-ol hydrochlorides. These secondary aminopropanols, whose synthesis is first reported here, were found not to have any significant antioxidant or antiradical activity either in an ascorbate-dependent Fe(II)-stimulated peroxidation system, in a method based on the spectrophotometric monitoring of decreases in the concentration of the stable radical 1,1-diphenyl-2-picrylhydrazyl, or in the photochemiluminescence analysis method. However these compounds had marked antihemolytic effects in an erythrocyte oxidative stress model. It is suggested that the new 1-(4-substituted phenyl)-2H-(phenyl)-3-aminopropan-1-ol hydrochlorides are biologically active compounds with weak antioxidant properties, capable of membrane-stabilizing actions due to interaction with the structural components of cell membranes.
Reactions of 4-fluorophenyl-b-morpholinopropiophenones with various Grignard reagents in anhydrous ether produced new tertiary aminoalcohols, 1-(4-fluorophenyl)-1-alkyl-2-phenyl-3-morpholinopropan-1-ols, that can be regarded as trihexyphenidyl (cyclodol) analogs. The antioxidant properties of the synthesized compounds were studied using a photochemiluminescence analytical method. It is established that the synthesized compounds exhibit antioxidant activity, the intensity of which depends on the length of the alkyl chain in the para-position of the benzene ring.
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