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1.
Russ Chem Bull ; 71(11): 2473-2481, 2022.
Article in English | MEDLINE | ID: mdl-36569656

ABSTRACT

A comparative evaluation of the antiviral activity of a number of new and previously synthesized terpenophenols and their N- or O-containing derivatives against the A/Puerto Rico/8/34 (H1N1) virus strain was carried out. 2-Isobornylphenol, 1,2-dihydroxy-6-isobornyl-4-methylbenzene, 2-isobornyl-1,4-benzoquinone, and N-butyl-4-hydroxy-3,5-diisobornylbenzamide showed the highest activity.

2.
Bull Exp Biol Med ; 173(6): 714-718, 2022 Oct.
Article in English | MEDLINE | ID: mdl-36322303

ABSTRACT

We studied the effect of antioxidants dibornol (2,6-diisobornyl-4-methylphenol) and its derivative (4-hydroxymethyl-2,6-diisobornylphenol), members of the alkylated phenols group, on the redox potential of male germ cells and their morphological and functional state in the rat model of pathospermia. Pharmacological effect was observed in animals treated with dibornol. The studied compounds led to the normalization of the antioxidant-prooxidant balance. However, the value of this indicator against the background of treatment with dibornol derivative attested to a shift in the redox balance of cells towards reduction reactions.


Subject(s)
Antioxidants , Phenols , Male , Animals , Rats , Antioxidants/pharmacology , Antioxidants/therapeutic use , Antioxidants/metabolism , Reactive Oxygen Species , Oxidation-Reduction , Phenols/pharmacology , Phenols/therapeutic use , Germ Cells/metabolism
3.
Bull Exp Biol Med ; 167(5): 606-609, 2019 Sep.
Article in English | MEDLINE | ID: mdl-31606803

ABSTRACT

Experimental model of sulpiride-provoked benign prostatic hyperplasia was employed to comparatively assess the effect of phenolic antioxidants (dihydroquercetin, p-thyrozol, dibornol, and prostagenin) on prostate morphology. All examined agents decreased the degree of hyperplasia in acinar epithelium; the greatest efficacy was demonstrated by prostagenin. Moreover, dihydroquercetin and p-thyrozol increased the cross-section area of acinar lumina and prostate volume, which is inadmissible in this pathology. These results suggest that the use of phenolic antioxidants in the therapy of benign prostatic hyperplasia should be strictly controlled.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Antioxidants/pharmacology , Methimazole/pharmacology , Phenols/pharmacology , Prostatic Hyperplasia/drug therapy , Quercetin/analogs & derivatives , Acinar Cells/drug effects , Acinar Cells/pathology , Animals , Animals, Outbred Strains , Disease Models, Animal , Humans , Male , Organ Size/drug effects , Prostate/drug effects , Prostate/pathology , Prostatic Hyperplasia/chemically induced , Prostatic Hyperplasia/pathology , Quercetin/pharmacology , Rats , Sulpiride/administration & dosage
4.
Bioorg Khim ; 40(1): 85-91, 2014.
Article in Russian | MEDLINE | ID: mdl-25898726

ABSTRACT

A series of water-soluble conjugates has been synthesized from polyethylene glycols of various lengths and 4-bromomethyl-2,6-diisobornylphenol. Evaluation of membrane protective and antioxidant activity of synthesized products on the model of H2O2-induced hemolysis of blood erythrocytes showed that conjugates have considerable antioxidant activity. A significant membrane protective effect was showed in conjugates with 0.2 and 0.8 mass. % of 2,6-diisobornyl-4-methylene fragments.


Subject(s)
Antioxidants/chemistry , Antioxidants/pharmacology , Polyethylene Glycols/chemistry , Animals , Antioxidants/chemical synthesis , Chemistry Techniques, Synthetic , Drug Evaluation, Preclinical/methods , Erythrocytes/drug effects , Hemolysis/drug effects , Hydrogen Peroxide/toxicity , Lipid Peroxidation/drug effects , Mice , Phenols/chemistry , Polyethylene Glycols/pharmacology , Solubility , Structure-Activity Relationship , Terpenes/chemistry , Water
5.
Bioorg Khim ; 39(4): 486-90, 2013.
Article in Russian | MEDLINE | ID: mdl-24707730

ABSTRACT

Two diastereomers of methylpheophorbide a 13(2)-N-n-octyl-N-(2-hydroxy-3-isobornyl-5-methylbenzyl)amide were obtained from (+)- and (-)-enantiomers of 2-isobornyl-4-methylphenol. Evaluation of membrane protective and antioxidant activity of individual diastereomers on the model of H2O2-induced hemolysis of blood erythrocytes showed that the stereochemistry of isobornyl substituent in the synthesized conjugates has no effect on their biological activity.


Subject(s)
Camphanes/chemistry , Chlorophyll/analogs & derivatives , Membranes/drug effects , Protective Agents/chemistry , Animals , Chlorophyll/chemical synthesis , Chlorophyll/chemistry , Chlorophyll/pharmacology , Chromatography, High Pressure Liquid , Cresols/chemistry , Erythrocytes/drug effects , Hydrogen Peroxide/chemistry , Mice , Molecular Structure , Protective Agents/chemical synthesis , Protective Agents/pharmacology , Stereoisomerism
6.
Bioorg Khim ; 38(5): 629-36, 2012.
Article in Russian | MEDLINE | ID: mdl-23342497

ABSTRACT

A series of terpenophenol-chlorin conjugates where terpenophenolic fragment has amide bond with macrocycle of methylpheophorbide a, formed by amidation of 13(2)-ester group were obtained by interaction of methylpheophorbide a and ortho-aminomethyl derivatives of 2-isobornyl-4-methylphenol. The substances investigated ability to interact with the cell membrane was shown in blood erythrocytes surface structure with scanning electron microscope. The conjugates studied were established to have antioxidant and membrane protective properties resulted from inhibiting H2O2-induced erythrocytes hemolysis and decrease of lipid peroxidation secondary product accumulation.


Subject(s)
Erythrocyte Membrane/chemistry , Hemolysis/drug effects , Hydrocarbons, Chlorinated , Lipid Peroxidation/drug effects , Phenols , Terpenes , Animals , Chlorophyll/analogs & derivatives , Chlorophyll/chemistry , Hydrocarbons, Chlorinated/chemical synthesis , Hydrocarbons, Chlorinated/chemistry , Hydrocarbons, Chlorinated/pharmacology , Mice , Phenols/chemical synthesis , Phenols/chemistry , Phenols/pharmacology , Terpenes/chemical synthesis , Terpenes/chemistry , Terpenes/pharmacology
8.
Bioorg Khim ; 37(5): 685-9, 2011.
Article in Russian | MEDLINE | ID: mdl-22332365

ABSTRACT

The resolution of the racemic ortho-isobornylphenol into enantiomers via diastereomeric camphanates was carried out. The absolute configuration ofchiral centers of synthesized compounds was established by the single crystal X-ray diffraction method. Antioxidant activity and membrane protective properties of individual enantiomers were studied on the model of H2O2-induced hemolysis of red blood cells.


Subject(s)
Antioxidants/chemistry , Antioxidants/pharmacology , Camphanes/chemical synthesis , Camphanes/pharmacology , Phenols/chemistry , Phenols/pharmacology , Animals , Cell Membrane/drug effects , Crystallography, X-Ray , Erythrocytes/drug effects , Hemoglobins/chemistry , Hemolysis , Hydrogen Peroxide/chemistry , Mice , Oxidation-Reduction , Stereoisomerism
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