Quercetin derivatives and synthetic method thereof

Abstract

The invention provides quercetin derivatives. The chemical structural general formulas of the quercetin derivative is as shown in the specification; and the synthetic method of the quercetin derivative comprises the following steps: (1) taking a carbonate and the like as the acid-binding agents and potassium iodide as the catalyst, and reacting the quercetin with a halogen substitute of fatty acid ethyl ester; (2) separating and purifying by silica gelcolumn chromatography, and collecting the same components to obtain three yellow powdery compounds: quercetin ester derivatives; and (3) taking the synthesized derivatives as the reactants, respectively, adding NaOH aqueous solution and taking polyethylene glycol as the phase transfer catalyst; separating and purifying by silica gelcolumn chromatography, and collecting the same components to obtain quercetin carboxylic acid derivatives, respectively. The synthetic method of the series quercetin derivatives provided by the invention is simple and easy to operate; the yield of each product is high; and the series quercetin derivatives are remarkably improved in both water solubility and lipid solubility compared with the quercetin.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a series of quercetin derivatives and a preparation method thereof. Background technique [0002] There are more than 6,000 natural flavonoids found in nature, among which quercetin (3,5,7,3',4'-pentahydroxy flavone) is the most widely existing flavonoid, with about 100 kinds This plant contains quercetin. Numerous scientific research results at home and abroad show that quercetin has a wide range of pharmacological effects and biological activities, such as anti-oxidation and scavenging oxygen free radicals, lowering blood pressure, protecting myocardial ischemia, avoiding ischemia-reperfusion injury, enhancing immune function and anti-cancer, Antibacterial, antiviral and analgesic effects, etc., and quercetin can inhibit the proliferation of human ovarian cancer, breast cancer, white blood cells, and gastrointestinal tumor cells. However, this compound contains mu...

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Problems solved by technology

However, this compound contains multiple polar groups, hydroxyl groups, and its lipophilicity is weak. At the same time, because the hydroxyl groups form hydrogen bonds between molecules, the lattice energy is high, and the hydrophilicity is also poor (the solubility of quercetin in water is 7ug / mL) , quickly absorbed and metabolized into the body, combined with sugar molecules and converted into glucuronide, etc. and inactivated, there is a strong first-pass effect, and the bioavailability is extremely low, resulting in low biological activity, so far it is difficult to be widely used as a drug in clinical practice Use (Zhao Chuzhong, Chinese Journal of Pharmacology, 1993,4: 263-265)

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