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Synthesis and Properties of New Dihydroquercetin Derivatives



Author(s)

Alexander M. Koroteev, Tatyana S. Kukhareva, Mikhail P. Koroteev, Garry Z. Kaziev, Sergey E. Mosyurov and Andrey T. Teleshev

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DOI:10.17265/2328-2150/2015.02.001

This paper is to analyze the latest data on synthesis, structure, chemical and biological properties of flavonoid dihydroquercetin (taxifolin). Complexes including DHQ (dihydroquercetin) into cyclodextrins were obtained. These supramolecular representatives are characterized by high water-solubility, good permeability through biomembranes, prolonged action in the organism and stability while being transported in bloodflow. The use of DHQ in complex with β-cyclodextrin is more promising from the medical point of view than the use of pure DHQ. Total and partial acidylation of DHQ with acid chlorides of aliphatic, aromatic, and heterocyclic carboxylic acids, as well as selective phosphorylation with acid derivatives of trivalent phosphorus (with amides and amidethers of phosphorous acid), and aminomethylation were carried out. DHQ freely undergoes Mannich Reaction with formaldehyde and amines of various structures. The products of the reaction are isolated from the reaction mix with good yield. Isolated aminomethylated derivatives have neurotropic and antiproliferative action.The structure of all synthesized compounds was proved with the help of modern methods of analysis: spectroscopy NMR (¹H, ¹³C) and XRS. Biological activity of dihydroquercetin modified derivatives was studied. It was found out that some of them are characterized by high cytotoxic, antitumour, and antioxidant biological activity. The inclusion complexes of dihydroquercetin and cyclodextrin were obtained. Acylation, phosphorylation and aminomethylation of dihydroquercetin was performed. The biological activity of obtained compounds was studied.

Flavonoids, dihydroquercetin, cyclodextrin, acylation, phosphorylation, aminomethylation, biological activity.

Alexander M. Koroteev., et al. 2015. “Synthesis and Properties of New Dihydroquercetin Derivatives.” Journal of Pharmacy and Pharmacology 3 (2): 43-57.