Tripterine derivate and use thereof

A technology of tripterycin and its derivatives, which is applied in the direction of drug combinations, steroidal compounds, and medical preparations containing active ingredients, etc., and can solve the problem of failure to explain the content of tripteryne and the failure to explain the effectiveness of tripteryne. Composition etc.

Inactive Publication Date: 2010-08-18
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The Chinese patent with the publication number CN00107779.1 discloses the application of a tripterygium plant extract in the prevention and treatment of nervous system diseases, including Alzheimer's disease, Parkins

Method used

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  • Tripterine derivate and use thereof
  • Tripterine derivate and use thereof
  • Tripterine derivate and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1 prepares tripterine methyl ester (synthetic route figure such as figure 1 shown)

[0041] Dissolve tripterine (20mg, 0.044mmol) in N,N-dimethylformamide (1ml) and stir to dissolve, add NaHCO 3 (19 mg, 0.22 mmol), followed by the addition of iodomethane (0.22 mmol). Stir the reaction at room temperature for 2 hours, stop the reaction and add deionized water (15ml), extract 3 times with ethyl acetate, combine the ethyl acetate layer, then wash the ethyl acetate layer 3 times with saturated NaCl, and wash with anhydrous NaCl 2 SO 4 Dry and concentrate with a rotary evaporator to obtain a dark red oil. The crude product was separated and purified by flash column chromatography (ethyl acetate: n-hexane), and the product was dried in vacuo to obtain 17 mg of dark red solid Cel-1 with a yield of 83%.

[0042] The mass spectrometric analysis of compound Cel-1 is as follows: MS(EI)[M+H] + m / z 465.6.MS(EI)[M+Na-H] + m / z 487.4. 1 H NMR (CDCl 3 , 400MHz): δ7.0...

Embodiment 2

[0043] Embodiment 2 prepares tripterine ethyl ester (synthetic route figure is as follows figure 1 shown)

[0044] Dissolve tripterine (20mg, 0.044mmol) in N,N-dimethylformamide (1ml) and stir to dissolve, add NaHCO 3 (19 mg, 0.22 mmol), followed by bromoethane (0.22 mmol). Stir the reaction at room temperature for 24 hours, stop the reaction and add deionized water (15ml), extract 3 times with ethyl acetate, combine the ethyl acetate layer, then wash the ethyl acetate layer 3 times with saturated NaCl, anhydrous NaCl 2 SO 4 Dry and concentrate with a rotary evaporator to obtain a dark red oil. The crude product was separated and purified by flash column chromatography (ethyl acetate: n-hexane), and the product was dried in vacuo to obtain 19 mg of dark red solid Cel-2 with a yield of 90%.

[0045] The mass spectrometric analysis of compound Cel-2 is as follows: MS(EI)[M+H] + m / z 479.9. 1 H NMR (CDCl 3 , 400MHz): δ7.03 (1H, dd, J=1.3, 7.1Hz, H-6), 6.56 (1H, d, J=1.4Hz, ...

Embodiment 3

[0046] Embodiment 3 prepares tripterine propyl ester (synthetic route figure is as follows figure 1 shown)

[0047] Dissolve tripterine (20mg, 0.044mmol) in N,N-dimethylformamide (1ml) and stir to dissolve, add NaHCO 3 (19 mg, 0.22 mmol), followed by bromopropane (0.22 mmol). Stir the reaction at room temperature for 24 hours, stop the reaction and add deionized water (15ml), extract 3 times with ethyl acetate, combine the ethyl acetate layer, then wash the ethyl acetate layer 3 times with saturated NaCl, anhydrous NaCl 2 SO 4 Dry and concentrate with a rotary evaporator to obtain a dark red oil. The crude product was separated and purified by flash column chromatography (ethyl acetate:n-hexane), and the product was dried in vacuo to obtain 16 mg of dark red solid Cel-3 with a yield of 74%.

[0048] The mass spectrometric analysis of compound Cel-3 is as follows: MS(EI)[M+H] + m / z493.6. 1 H NMR (CDCl 3 , 400MHz): δ7.04 (1H, dd, J=1.4, 7.1Hz, H-6), 6.60 (1H, d, J=1.4Hz, ...

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Abstract

The invention discloses a tripterine derivate and use thereof. The tripterine derivate has a structure as shown by a formula I. When R2 is H, R1 is alkyl, amine radical, alcohol, aryl, mixed aryl or heterocyclic radical connected with tripterine through ester bonds or amido bonds, and R2 is acyl or organic acid radical when R1 is OH. The tripterine derivate can be used for preparing anticancer medicine, anti-inflammatory medicine or medicine for treating central nervous system diseases. The medicine can be made into tablets, capsules, granules, fine grains, powder, pills, plaser, oral liquid or injections.

Description

technical field [0001] The invention belongs to the technical field of traditional Chinese medicines, in particular to a tripterine derivative and its application. Background technique [0002] With age, the body's oxidative defense mechanism is disordered, and the oxidative damage caused by reactive oxygen species (ROS) also increases, and studies have shown that oxidative damage is one of the causes of many diseases such as cancer and local ischemia. Aerobic organisms have a defense mechanism centered on antioxidant enzymes against oxidative damage caused by free radicals. If this balance is disrupted, oxidative stress will be generated and cell damage will be caused. The targets of oxidative stress are lipids, proteins, and nucleic acids. [0003] The brain and nerves are organs with a high oxygen consumption rate, because they contain a large amount of lipids, they are prone to become fragile due to oxidative stress caused by free radicals, and nerve cells are highly di...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P35/00A61P29/00A61P25/00A61K31/58A61K31/56
Inventor 王玉强孙红莉徐立朋于沛张高小蒋杰单璐琛
Owner JINAN UNIVERSITY
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