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Rheinic acid derivatives and treatment application thereof

A technology of rhein and derivatives, applied in the field of medicine, can solve the problems of high pH value of water injection, unacceptable human physiology, poor preparation stability, etc., and achieve obvious pharmacological activity effect

Active Publication Date: 2011-10-26
南通东湖国际商务服务有限公司
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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 a new type of rhein compound and other compounds with biologically active compounds formed by splicing together, not only to increase its water solubility, but also to overcome the alkalinity of the rhein compound's strong alkali salt solution, and to make The pH value of the water injection is high, which is difficult for the human body to accept; if the pH value is lowered, the stability of the preparation is not good.

Method used

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  • Rheinic acid derivatives and treatment application thereof
  • Rheinic acid derivatives and treatment application thereof
  • Rheinic acid derivatives and treatment application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of Ligustrazine Rheinate

[0032] 1.1 The synthesis of 2-bromomethyl-3,5,6-trimethylpyrazine (synthesis of bromoligustrazine)

[0033] In a 250ml three-necked flask, sequentially add the raw materials 2,3,5,6-tetramethylpyrazine (20g, 0.147mol), NBS (26.75g, 0.15mol), and benzoyl peroxide (0.05g, 0.0002mol) , The solvent tetrahydrofuran (75mL). The solution was orange-yellow and turbid. Irradiated by incandescent lamp, the oil bath was heated to 75℃, and the reaction was refluxed for 8 hours. TLC [V (ethyl acetate): V (petroleum ether) = 1:2 as the developing solvent] showed that the reaction was complete (raw material) Rf=0.38, product Rf=0.56), the reaction solution was purple-red, the succinimide produced was removed by filtration to obtain purple-red filtrate, the purple-red viscous liquid after tetrahydrofuran was recovered under reduced pressure, and the product was collected by vacuum distillation 99~101℃ / 2mmHg distillate yields 23g of 2-bromomethyl-3,5,6-...

Embodiment 2

[0041] Synthesis of 2,3,4,6-tetraacetylglucose ester of rhein;

[0042] Add rhein (0.68g, 0.0024mol), K 2 CO 3 0.69g, water (10ml), heated to 30°C and stirred to dissolve, the pH of the solution was controlled to be ≈9. Add 10ml of dichloromethane with 0.20g of tetrabutylammonium bromide, continue stirring at 30°C for 30min, and add 10ml of dichloromethane solution of 1.02g (0.0025mol) of 2,3,4,6-tetraacetylglucose bromide dropwise. After the addition is complete, heat to 50°C and stir for 6 hours. TLC shows that the reaction is complete. Separate the organic layer, extract the aqueous layer 3 times with dichloromethane, combine the organic phases, and wash the organic phases with 2% NaOH solution to neutrality. , Dried over anhydrous sodium sulfate, recovered chloroform under reduced pressure, and recrystallized from absolute ethanol to obtain 0.75 g of red solid, with a yield of 51%.

[0043] Reaction formula:

[0044]

[0045] The compound of Example 1 has shown efficacy in xyle...

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Abstract

The invention discloses rheinic acid derivatives and treatment application thereof, belonging to the field of medicine. A compound with a bioactivity is a compound as shown in a general formula (I) or salts, solvates or hydrates thereof, wherein X3 is the residue of the compound with the bioactivity, and X1 and X2 are independently H or acetyl individually; X3 is the residue of ligustrazine, arginine, lysine or carnitine; X3 is the residue of meglumine, glucosamine or glucose; and X3 is the residue of meglumine, glucosamine or glucose acetylate. The treatment application is as follows: the rheinic acid derivatives can be used for preparation of medicaments for treating or preventing heart cerebrovascular diseases, and can also be used for preparation of medicaments for treating or preventing diseases related to T-cell proliferation or diseases mediated by pro-inflammatory cytokines.

Description

Technical field [0001] The invention belongs to the field of medicine, especially rhein derivatives and their therapeutic uses. technical background [0002] Rhein (RH) is an anthraquinone substance, which is widely present in Polygonaceae (Polygonaceae) rhubarb (Rheum) plant palm leaf rhubarb (R.palmatum L.), Tanguticum.Maximex Regel (R.tanguticum.Maximex Regel) ) And the roots and roots of medicinal rhubarb (R.officinal.Baill), studies have found that RH has a wide range of pharmacological activities, such as anti-tumor, anti-inflammatory, antibacterial and regulating renal function, especially in anti-inflammatory activities. Has been applied. At present, rhein has become the best raw material for formulating health products, which can be used for reducing fat and losing weight, laxative detoxification, cleansing the internal environment, preventing gastric cancer, and delaying aging. Vigorously developing various natural health foods rich in rhein will have good economic be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/12C07H13/08A61K31/4965A61K31/7024A61P9/00A61P35/00A61P29/00
Inventor 栗进才黄鹏刘耀武
Owner 南通东湖国际商务服务有限公司
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