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.
Interaction of a-phenyl-b-piperidino-4-substituted propiophenones with Grignard reagents in ether was used to synthesize 1-(4-substituted phenyl)-1-alkyl(aryl)-2-phenyl-3-piperidinopropan-1-ols. The antibacterial and antioxidant properties of the aminopropanol hydrochlorides were studied. Some of these compounds (3-(4-ethoxyphenyl)-2-phenyl-1-piperidinoheptan-, 3-(4-ethoxyphenyl)-2-phenyl-1-piperidonooctan-, and 2-phenyl-1-piperidino-3-(4-propoxyphenyl)decan-3-ol hydrochlorides) had moderate antibacterial activity and some (3-(4-ethoxyphenyl)-2-phenyl-1-piperidinopentan-and 3-(4-ethoxyphenyl)-5-methyl-2-phenyl-1-piperidinohexan-3-ol hydrochlorides) had high antioxidant activity.Extensive data on the biological properties of ternary aminopropanols synthesized by ourselves create the need for widening and deepening their study. In continuation of our previous reports [1-4] on the "structure-biological activity" relationships of cyclodol analogs (1-cyclohexyl-1-phenyl-3-piperidinopropan-1-ol hydrochlorides), interaction of b-aminoketones with a variety of Grignard reagents was used to prepare a new series of aminopropanols, II. We have previously demonstrated that tertiary aminopropanols have a variety of biological properties [5,6]. The aims of the present work were to synthesize 1-(4-substituted phenyl)-1-alkyl-(aryl)-2-phenyl-3-piperidinopropan-1-ols (II) in which the hydrogen atom of the keto group in the a position is substituted by a phenyl radical and the amine fragment is piperidine, and to study the biological properties of aminopropanol hydrochlorides III -XX.The b-piperidinopropiophenones (I) required for the synthesis were prepared as described in [7]. The biological properties of aminopropanols (II) were studied after conversion to the corresponding hydrochlorides (III-XX); the antibacterial and antioxidant activities of these compounds were assessed.The structures of the compounds synthesized were confirmed by IR and 1 H NMR spectroscopy.
EXPERIMENTAL CHEMICAL SECTIONIR spectra were recorded on Specord 75-IR and FT-IR Nexus instruments and 1 H NMR spectra on a Mercury-300 224 0091-150X/11/4504-0224
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