Reactions of catechin and dihydroquercetin flavonoids with amino acids containing primary amino groups have been conducted. Amino acids can be used in both electrophilic substitution (Mannich aminomethylation) and electrophilic substitution (acylation) reactions.
The reactivity of dihydroquercetin and catechol flavonoids in acylation, phosphorylation, and aminomethylation reactions was compared. The structure of natural polyatomic phenols was shown to affect markedly their chemical behavior.
The ability of a water-soluble inclusion complex (KN-14-CD) of an aminomethylated dihydroquercetin derivative (KN-14) in β-cyclodextrin (CD) to inhibit ozone-induced oxidation of fibrinogen was evaluated. KN-14-CD prevented ozone-induced oxidation of fibrinogen and preserved its ability to form clots after the addition of thrombin. The ability of KN-14-CD to prevent oxidative modification of fibrinogen was more pronounced than that of native dihydroquercetin (taxifolin).
Оценивается влияние водорастворимого комплекса включения нового аминометилированного производного дигидрокверцетина в циклодекстрин (КН-14-ЦД) на окисление фибриногена. Соединение КН-14-ЦД предотвращает окислительную деструкцию фибриногена, вызванную озоновым окислением, сохраняя способность фибриногена формировать фибриновый сгусток после добавления тромбина. КН-14-ЦД более эффективно предохраняет фибриноген от окислительной деструкции, чем нативный дигидрокверцетин.
Reaction of dihydroquercetin with acid chlorides of higher and functionalized carboxylic acids was studied with the purpose of creation of new pharmaceuticals.
Effect of nine new derivatives of dihydroquercetin (taxifolin) on the viability of cultivated normal and tumor cells, their antioxidant activity, and interconnection of the antioxidant activity with the chemical structure have been studied. Among these dihydroquercetin derivatives, the maximum antiproliferative activity on the model of rat fibroblast culture exhibited KN-2, KN-4, KN-7, and KN-8 compounds, while KN-7 and KN-8 compounds also showed maximum activity on the model of MCF-7 tumor cell culture (human breast cancer). The maximum general antioxidant activity was observed for the native dihydroquercetin and KN-8 compound. There is a strong correlation (with a correlation coefficient of 0.93) between the antiproliferative effects of dihydroquercetin derivatives on murine skin fibroblasts and MCF-7 cells (human breast cancer).
The possibility was demonstrated and conditions were developed of a directional phosphorylation of dihydroquercetin flavonoid with phosphorous hexaethyltriamide. The chemical properties of the obtained compounds of trivalent phosphorus are currently under investigation.
Effect of nine new derivatives of dihydroquercetin (taxifolin) on the viability of cultivated normal and tumor cells, their antioxidant activity, and interconnection of the antioxidant activity with the chemical structure have been studied. Among these dihydroquercetin derivatives, the maximum antiproliferative activity on the model of rat fibroblast culture exhibited KN-2, KN-4, KN-7, and KN-8 compounds, while KN-7 and KN-8 compounds also showed maximum activity on the model of MCF-7 tumor cell culture (human breast cancer). The maximum general antioxidant activity was observed for the native dihydroquercetin and KN-8 compound. There is a strong correlation (with a correlation coefficient of 0.93) between the antiproliferative effects of dihydroquercetin derivatives on murine skin fibroblasts and MCF-7 cells (human breast cancer).
The monophosphorylated products were obtained by phosphorylation of 2,3-dihydroquercetin with phosphorous acid amides. Sulfur addition to these compounds was studied.
Synthesis and chemical properties of the first carbohydrate phenylphosphonites are described.
Palladium-catalyzed arylation of hydrophosphorylated protected monosaccharides of the pyranose and furanose series gave the corresponding P-aryl derivatives.