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Ether derivative of resveratrol and medical application

A technology of resveratrol and derivatives, applied in the field of medicine, can solve the problems of short-term therapeutic effect, fast biological metabolism, etc., and achieve the effects of convenient medication, prolonged action time, and difficult inactivation

Active Publication Date: 2012-09-19
西安天一生物技术股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide an ether derivative of resveratrol and its therapeutic use, which can solve the problems that resveratrol itself is easily hydrolyzed in the living body, the biological metabolism is fast, and the short t1 / 2 in the body affects the therapeutic effect.

Method used

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  • Ether derivative of resveratrol and medical application
  • Ether derivative of resveratrol and medical application
  • Ether derivative of resveratrol and medical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of Resveratrol Trioxane

[0039] Take 0.68g (6.24mmol) of bromoethane and potassium carbonate (8.5g, 0.062mol) into a three-necked flask with a stirring device, and add 20ml of DMF. After stirring evenly, add 0.39g of resveratrol (1.71mmol) and 10ml of DMF dropwise. After the dropwise addition, the temperature was raised to 95°C, and the reaction was continued for 5h. After filtering, the filtrate was rotary evaporated under reduced pressure, and the organic solvent was recovered to obtain a yellow solid. Separation by column chromatography yielded 0.32 g of resveratrol trioxane with a yield of 71.2%. 1 H-NMR (CDCl 3 , 300MHz) δ: 7.3 (m, 2H), 6.8 (4H, m), 6.6 (2H, d), 6.2 (1H, t), 4.2-4.3 (6H, m), 1.4-1.5 (9H, m) ; m / e: 312.

Embodiment 2

[0041] Synthesis of Resveratrol Trioxo-3-Methylpyridine

[0042] Weigh resveratrol (3.9g, 0.017mol) and potassium carbonate (8.5g, 0.062mol) into a 250mL three-necked bottle. Add DMF (100mL), heat to 100°C, then add 3-chloromethylpyridine hydrochloride (10.4g, 0.062mol) in portions within 10min, keep the reaction at 95°C, heat the reaction for 4h, and detect the degree of reaction by TLC. After the reaction is basically completed, cool to room temperature, filter the filtrate with suction, add 100mL of water, extract with ethyl acetate 100mL×3, combine the ethyl acetate layers and wash with water (50mL×3), dry with anhydrous sodium sulfate, and depressurize After recovering ethyl acetate, a yellow solid was obtained, which was separated through a silica gel column, and the product was collected. After recovering the solvent under reduced pressure, 6.54 g of resveratrol trioxo-3-methylpyridine was obtained as a light yellow solid, with a yield of 65.1%; 1 H NMR (CDCl 3 , 300M...

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Abstract

The invention provides an ether derivative of resveratrol and medical application, and belongs to the field of medicines. The compound with bioactivity is a compound of the general formula (I), salt, solvate or hydrate thereof, wherein X1 is H or CH2R1, X2 is H or CH2R2, X3 is H or CH2R3, but X1, X2 and X3 are not all H, and X1, X2 and X3 can be the same; R1, R2 and R3 are same or different, each of the R1, R2 and R3 is C1-6 alkyl substituted by R4, or 4-7 member ring which can be substituted by R9 arbitrarily and contains one or more additional heteroatom of O, S(O)n and NR9; R4 is F, CF3, OR5, NR6R7 or S(O)nR8; R5, R6 and R7 are same or different, each of the R5, R6 and R7 is C1-6 alkyl substituted by R4 arbitrarily, or NR6R7 is 4-6 heterocyclic alkyl ring containing heteroatoms of one or more O, NR9 and S(O)n; each n is 0-2; R8 is C1-6 alkyl; R9 is C1-4 alkyl defined by R4 or arbitrarily substituted by R4 or halogen; and R9 is H or C1-6 alkyl. The ether derivative can be applied to treatment of hepatic diseases, T-cell proliferation related or proinflammatory cytokine induced diseases.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to ether derivatives of resveratrol and their therapeutic use. technical background [0002] In 1989, the epidemiological survey of the world cardiovascular disease control system of the World Health Organization (WHO) confirmed that the phenomenon of "French paradox" is closely related to France being the largest wine production and consumption country in the world, because there is a The substance called Resveratrol (Res for short) has a very significant effect of preventing coronary heart disease, and this discovery has triggered an upsurge of scientists' research on resveratrol. Resveratrol, whose chemical name is glucosinolate, has two configurations: cis and trans, the latter is the stable structure of Res, and has a wider range of biological activities. Its structural formula is: [0003] [0004] This compound was originally discovered as an anti-stress substance of grape plants...

Claims

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Application Information

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IPC IPC(8): C07C43/215C07C41/16C07D213/30A61K31/4406A61K31/09A61P1/16A61P29/00
Inventor 牛婧牛倩
Owner 西安天一生物技术股份有限公司
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