A kind of synthetic method and application of flavonoids

The technology of a flavonoid compound and a synthesis method, which is applied in the field of medicinal chemistry synthesis, can solve the problems of low yield, lack of 5-hydroxy flavonoids, troublesome separation and purification, etc., and achieves the effects of cheap and easy-to-obtain raw materials and wide adaptability.

Inactive Publication Date: 2015-10-28
SHANGLUO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010], but the yield of this method is very low, and they also It was found that when the 6-position of 2-hydroxyacetophenone has no hydroxyl group or the hydroxyl group is protected, only β-propanedione-based products can be obtained by the one-pot method, and 5-hydroxyflavone cannot be obtained
Inspired by the Bois method, the applicant conducted a systematic study on the Baker-Venkataraman reaction catalyzed by potassium carbonate, and found that only when the 6-position of 2-hydroxyacetophenone has a hydroxyl group, such as 2,6-dihydroxybenzene Ethyl ketone and 2,4,6-trihydroxyacetophenone, they can directly obtain flavones with benzoyl chloride and its derivatives in acetone solution of potassium carbonate, but the yield is extremely low, such as 5-hydroxyflavone yield 11.6 %, the yield of 4'-fluoro-5-hydroxyflavone is 9.0%, the yield of 4'-chloro-5-hydroxyflavone is 9.7%, and the separation and purification are troublesome

Method used

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  • A kind of synthetic method and application of flavonoids
  • A kind of synthetic method and application of flavonoids
  • A kind of synthetic method and application of flavonoids

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Take 11.0 g (0.1 mol) of resorcinol, 15.4 mL of glacial acetic acid, and 16.3 g (0.12 mol) of dry zinc chloride, mix them, heat in an oil bath to 140.0-150.0°C, and stir for 2.0 h under reflux. TLC monitored the completion of the reaction, cooled to room temperature, poured the reaction solution into ice water to cool, and suction filtered. The filter cake was washed several times with dilute hydrochloric acid to remove zinc salts, and an orange-yellow solid was obtained. The solid was heated and dissolved with dilute hydrochloric acid, decolorized with activated carbon, and then recrystallized repeatedly with dilute hydrochloric acid to finally obtain orange-yellow crystals of 2,4-dihydroxyacetophenone (compound 2, 10.0 g, 0.0657 mol).

[0053] Add 2,4-dihydroxyacetophenone (2.46 g, 16.2 mmol) to the reaction flask, anhydrous K 2 CO 3(22.69g, 162.0 mmol), and dry acetone (60 mL), refluxed in an oil bath at 60°C for 10 min, and added anhydrous pyridine (1.28g, 16.2 mm...

Embodiment 2～13

[0061] Synthesis of other flavonoids

[0062] The synthesis steps of other flavonoids were carried out according to the synthesis steps of 7-hydroxyflavone in Example 1.

[0063] Wherein, used reactant and target product are as follows:

[0064] .

[0065] The consumption and reflux condition of each raw material in each embodiment are as follows:

[0066] .

[0067] The character of each product of embodiment 2~13 gained

[0068] 4′-Fluoro-7-hydroxyflavone: yellow needle crystal, the yield is about 95.7%, melting point: 250~254 ℃; 1 H NMR (400 MHz, Acetone) δ 9.74 (s, 1H,-OH), 8.29 – 8.12 (m, 2H,2′, 6′-H), 8.03 (d, J = 8.7 Hz, 1H, 5-H), 7.42 (t, J = 8.8 Hz, 2H,3′, 4′- H), 7.12 (d, J = 2.2 Hz, 1H,8-H), 7.05 (dd, J = 8.7, 2.3 Hz, 1H,6-H), 6.79 (s, 1H,3-H); ESI-MS (positive): calcd for C 15 h 9 o 3 F([M+Na] + ) 257.24; found 257.00(M+H) + .

[0069] 4′-Chloro-7-hydroxyflavone: white needle crystal, the yield is about 92.7%, melting point: 284.9~286℃; 1 H ...

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Abstract

The invention discloses a synthetic method and application of a flavonoid. The method employs a solvent of acetone, and a 2-hydroxy acetophenone derivative and aryl formyl chloride are subjected to heating reaction in the catalysis of potash and pyridine to obtain the flavonoid. The structural formulas of the 2-hydroxy acetophenone derivative, aryl formyl chloride and the flavonoid are shown as below. The invention employs potash and pyridine as catalysts for the one-step reaction of 2-hydroxy acetophenone derivative and aryl formyl chloride to prepare the flavonoid; and compared with an existing synthetic method, the method has advantages of low price of catalyst, wide scope of adaptation of the flavonoid product to raw materials and reactant yield reaching more than 90%.

Description

technical field [0001] The invention belongs to the field of pharmaceutical chemical synthesis, and in particular relates to a synthesis method and application of flavonoids. Background technique [0002] Flavonoids are widely distributed in nature and are secondary metabolites of plants with broad-spectrum physiological activities. However, due to the poor solubility and low bioavailability of flavonoids, coupled with their extremely wide range of physiological activities, multiple targets, and lack of selectivity for disease treatment, such phenomena limit the direct development of flavonoids into new drugs. Therefore, it is of great practical significance to further modify and derivatize the structure of flavonoids by chemical synthesis to solve the difficulties brought by the above problems to the development of new flavonoids. [0003] There are two main synthetic methods of flavonoids, namely chalcone route and β-propanedione route (Baker-Venkataraman method). The cl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30C07D405/12
Inventor 王学军王新军张晓文
Owner SHANGLUO UNIV
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