Fluoro flavon containing compound, manufacturing method and its use

A technology of flavonoids and compounds, applied in medical preparations containing active ingredients, organic chemistry, drug combinations, etc., can solve problems such as weak biological activity

Inactive Publication Date: 2004-02-18
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these compounds can improve the effect of flavonoids to a certain extent (such as enhancing the inhibitory effect on ...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0060] Embodiment 14'-trifluoromethyl-5, the preparation of 7-dihydroxyflavone (code name 101):

[0061] Add 0.05mol phloroglucinol, 0.1mol chloroacetonitrile and 25ml anhydrous diethyl ether into the three-neck flask, cool with an ice-salt bath, add 1.3 grams of anhydrous ZnCl under stirring 2 , After passing dry hydrogen chloride gas for 2 hours, place the reaction bottle in a zero-degree refrigerator for one day, then pass hydrogen chloride for 2 hours, and place it in a zero-degree refrigerator for three days. Pour out ether, wash twice with anhydrous ether, transfer the crude product to a round-bottomed flask with about 250ml of hot water, reflux for 1 hour, and let it stand overnight. Orange crystals precipitate, filter with suction, and crystallize with water to obtain light yellow needle crystals 1. The yield is 68%.

[0062] Add 9.64 mmol of compound 1 to the three-necked flask, dissolve it in 95 ml of methanol, add 16.1 mmol of p-trifluor...

Embodiment 24

[0064] The preparation of embodiment 24'-trifluoromethyl-7-hydroxyflavone (code name 102):

[0065] Replace phloroglucinol with 0.05mol resorcinol to prepare 4'-trifluoromethyl-7-hydroxyflavone according to the method of Example 1, with a yield of 90%.

[0066] The relevant data are as follows: MS (EI, 70ev) m / z: 306; IRυ max (cm -1 , KBr): 1683 (C=O), 3072 (OH); 1 H NMR (300MHz, CD 3 COCD 3 ): 6.818 (1H, s), 6.857 (1H, dd, J=2.1, 8.4), 6.899 (1H, d, J=2.1), 7.692 (1H, d, J=8.4), 7.774 (2H, d, J=6.8), 8.220(2H, d, J=6.8), 10.138(1H, s). 19 F NMR(300MHz)-68.627.Anal.Calcd.for C 16 h 9 f 3 o 3 : C, 62.75, H, 2.96; Found C, 62.90, H, 3.44.

Embodiment 33

[0067] Embodiment 33'-trifluoromethyl-5, the preparation of 7-dihydroxyflavone (code name 103):

[0068] Using 0.05mol 3'-trifluoromethylbenzaldehyde instead of 4'-trifluoromethylbenzaldehyde to prepare 3'-trifluoromethyl-5,7-dihydroxyflavone according to the method of Example 1, the yield is 91% .

[0069] The relevant data are as follows: MS (EI, 70ev) m / z: 322; IRυ max (cm -1 , KBr): 1680 (C=O), 3092, 3308 (OH); 1 H NMR (300MHz, DMSO-d 6 ): 6.102(1H, d, J=1.5), 6.222(1H, d, J=1.5), 6.687(1H, s), 7.806-7.963(4H, m), 11.012(1H, s), 11.102(1H , s). 19 FNMR (300MHz)-70.65; Anal.Calcd.for C 16 h 9 f 3 o 4 : C, 59.64, H, 2.82; Found C, 59.74, H, 2.88.

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Abstract

A fluoric flavone compound and its preparing process are disclosed. Said compound can be used to prepare medicines for treating cancer, hypertension, hyperglycemia, dysphoria and bacterial and viral diseases. The compound is prepared by introducing fluorine-containing group into flavone-like compound. Its advantage is high curative effect and low poison.

Description

technical field [0001] The present invention relates to a class of fluorine-containing flavonoids, a production method and its application, in particular to a class of fluorine-containing flavonoids with anti-cancer, blood pressure-lowering, blood-sugar-lowering, sedative, anti-anxiety, antibacterial and anti-viral effects . Background technique [0002] Flavonoids are widely distributed in the plant kingdom, and about 20% of Chinese herbal medicines contain flavonoids (Tu Shizhong. Pharmaceutical Bulletin, 1979, 14:37), which are used as natural dyes and oil preservatives in industry. Pharmacological studies have shown that flavonoids have multiple physiological activities and pharmacological effects such as dilating coronary arteries, anti-inflammatory, antibacterial, anti-tumor, lowering blood pressure, preventing and treating bronchitis, and protecting the liver (Wang Lanming, Chinese Journal of Pharmaceutical Industry, 1990, 21( 9): 423). However, the biological activ...

Claims

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Application Information

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IPC IPC(8): A61K31/352A61P3/10A61P9/12A61P25/20A61P25/22A61P31/04A61P31/12A61P35/00C07D311/30
Inventor 卿凤翎郑兴王若文
Owner DONGHUA UNIV
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