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Amino acid modified curcumin, synthesis method thereof, and application thereof

A technology of oxyacetyl amino acid benzyl ester group and seryl group, which is applied in the field of curcumin derivatives, can solve the problems of application limitations, low absorption in the body, and excessive metabolism

Inactive Publication Date: 2011-11-16
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, recent studies have found that curcumin's anti-tumor activity in vivo is low, its absorption in the body is low, its metabolism is too fast, and its application is limited.

Method used

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  • Amino acid modified curcumin, synthesis method thereof, and application thereof
  • Amino acid modified curcumin, synthesis method thereof, and application thereof
  • Amino acid modified curcumin, synthesis method thereof, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1 prepares 3-methoxy-4-(2-butyryloxy) benzaldehyde (1)

[0022] 10 g (65.7 mmol) of vanillin were dissolved in 200 ml of anhydrous THF. To the resulting solution, 11.8 g (85.6 mmol) of potassium carbonate was added in portions and stirred for 2 h. Then 7.68ml of ethyl bromoacetate was added dropwise, and stirred vigorously at room temperature for 48h. TLC plate monitoring (petroleum ether:ethyl acetate=3:1) showed that the reaction was complete. The reaction mixture was suction filtered, and the filtrate was concentrated to dryness under reduced pressure. The obtained residue was dissolved in 150 mL of ethyl acetate, placed in a 250 mL separatory funnel, washed successively with 5% potassium hydrogensulfate aqueous solution (30 mL×3), and saturated sodium chloride aqueous solution (30 mL×3). The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness under reduced pressure to obtain 10.9 g (70%) of...

Embodiment 2

[0023] Example 2 Preparation of 6-(4-hydroxyl-3-methoxyphenyl)-5,6-hexene-2,4-dione (2)

[0024] Add 10.58ml (102.9mmol) of acetylacetone, 5.0g (72.1mmol) of boron oxide and 50.0mL of ethyl acetate into a 150mL three-necked flask, install a reflux condenser, and stir for 1 hour at a constant temperature of 70°C in an oil bath. Then 5.2 g (34.3 mmol) of vanillin and 4.8 ml (34.3 mmol) of tributyl borate were added. The reaction mixture was stirred at 85 °C for 30 min. 1.8 mL (41.1 mmol) of triethylamine diluted in 10 mL of ethyl acetate was slowly added dropwise to the three-necked flask within 30 min, reacted at 100° C. for 1 h, and then cooled to room temperature. Add 36mL of hydrochloric acid (1N) dropwise to the reaction flask, stir at 50°C for 30min, let stand, and fully separate the layers. The aqueous layer was extracted 3 times with ethyl acetate, the ethyl acetate layers were combined, washed with water until neutral, dried over anhydrous sodium sulfate, filtered, th...

Embodiment 3

[0025] Example 3 Preparation of 1-(4-hydroxyl-3-methoxyphenyl)-7-(4-oxyacetoethoxy-3-methoxyphenyl)-1,6-heptadiene-3, 5-diketone(3)

[0026]Add 5.0g (21.4mmol) 6-(4-hydroxyl-3-methoxyphenyl)-5,6-hexene-2,4-dione (2), 1.0g (14.9mmol ) boron oxide and 50.0 mL ethyl acetate. Install the reflux condenser. The reaction mixture was stirred at 70 °C for 1 h. Then 4.3 g (18.1 mmol) of 3-methoxy-4-(2-butyryloxy)benzaldehyde (1) and 3.7 ml (21.4 mmol) of tributyl borate were added. The reaction mixture was stirred at 85 °C for 30 min. 0.98 mL (21.4 mmol) of n-butylamine diluted in 10 mL of ethyl acetate was slowly added dropwise to the three-necked flask within 30 min. The reaction mixture was continued at 100 °C for 1 h, then cooled to room temperature. Add 19.6 mL of hydrochloric acid (1N) to the reaction mixture, stir the reaction at 50°C for 30 min, let it stand still, separate the layers sufficiently, and extract the aqueous layer with ethyl acetate three times. The combined...

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Abstract

The invention discloses a type of amino acid modified curcumin, a synthesis method thereof, and an application thereof. According to the invention, structural modification is carried out upon curcumin by using natural amino acid, such that 1-(4-hydroxy-3-methoxyphenyl)-7-(4-oxyacetyl amino carbobenzoxy-3-methoxyphenyl)-1,6-heptadiene-3,5-diketone which is represented by a general formula (I) is obtained. With an MTT method, evaluation is carried out upon the compound represented by the general formula (I) in the inhabitance of proliferation activities of four cells which are K562, H22, HL60 and S180. IC50 values of the compound represented by the general formula (I) in inhibiting the proliferations of the four tumor cells are calculated. As a result of experiments, with the compound represented by the general formula (I), proliferations of tumor cells can be substantially inhibited. The compound has excellent anti-tumor activity, and can be prepared into anti-tumor medicines.

Description

technical field [0001] The present invention relates to amino acid modified curcumin, in particular to 1-(4-hydroxyl-3-methoxyphenyl)-7-(4-oxoacetylamino acid benzyl ester-3-methoxyphenyl)-1, 6-heptadiene-3,5-dione and its synthesis method, the present invention further relates to 1-(4-hydroxy-3-methoxyphenyl)-7-(4-oxoacetylamino acid benzyl ester group-3 The clinical application of -methoxyphenyl)-1,6-heptadiene-3,5-dione as an antitumor drug belongs to the field of derivatives of curcumin. Background technique [0002] Curcumin [(1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione] is the active ingredient of the traditional Chinese medicine turmeric, which has a wide range of pharmacological Nature, in 1985, Kuttan in India first proposed the possibility that turmeric and curcumin have anti-tumor effects. Since then, many scholars have studied the anti-tumor effects and mechanisms of curcumin, and believe that curcumin can inhibit the growth of tumor cell lines....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/20C07C231/02C07D207/16C07C323/59C07C309/20C07D209/20C07C279/14C07C277/08C07C237/22A61K31/216A61K31/401A61K31/405A61P35/00
Inventor 赵明彭师奇张筱宜
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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