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Tripterine derivative, biogenetic salt of derivative, and preparation method and application of biogenetic salt

A technology of tripterine and its derivatives, which is applied in the direction of drug combination, steroids, digestive system, etc., can solve the problems of little research on liver fibrosis, achieve good hepatic stellate cell activation and increase, and improve bioavailability , The effect of water solubility improvement

Active Publication Date: 2014-01-22
ANHUI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that tripterine can prevent and treat lupus nephritis glomerulosclerosis, inhibit bronchial asthma airway inflammation, and have significant protective effects on colitis rats. It can also induce tumor cell apoptosis and inhibit tumor blood vessels. Role of endothelial cell growth, but poorly studied in liver fibrosis

Method used

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  • Tripterine derivative, biogenetic salt of derivative, and preparation method and application of biogenetic salt
  • Tripterine derivative, biogenetic salt of derivative, and preparation method and application of biogenetic salt
  • Tripterine derivative, biogenetic salt of derivative, and preparation method and application of biogenetic salt

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation of derivative a (synthetic route such as figure 1 shown)

[0031] Dissolve tripterine (20mg, 0.044mmol) in dichloromethane (3ml), add EDC·HCl (43mg, 0.22mmol), HOBT (30mg, 0.22mmol), methylamine hydrochloride (23mg, 0.35mmol) , stirred in an ice bath for 30 min, added triethylamine (50 μl), stirred at room temperature for 12 h, extracted 3 times with dichloromethane, combined organic layers, and anhydrous Na 2 SO 4 Dry and concentrate by rotary evaporation to give the crude product as a dark red oil. The crude product was separated and purified by fast silica gel column chromatography (the mobile phase was a mixture of petroleum ether and ethyl acetate with a volume ratio of 1:1), and the product was dried in vacuo to obtain 8 mg of a dark red solid, which was derived from tripterine. Material a, the yield is 39%.

[0032] The spectral analysis of the tripterine derivative a is as follows: M.p.133°C; 1 H-NMR (400MHz, CDCl 3 ),δ(ppm):6.98(d,1H,J=4.4...

Embodiment 2

[0034] The preparation of derivative b (synthetic route such as figure 1 shown)

[0035] Tripterine (20mg, 0.044mmol) was dissolved in dichloromethane (3ml), added EDC·HCl (43mg, 0.22mmol), HOBT (30mg, 0.22mmol), dimethylamine hydrochloride (30mg, 0.37mmol), ice Stir in the bath for 30 min, add triethylamine (50 μl), stir at room temperature overnight, extract 3 times with dichloromethane, combine organic layers, anhydrous Na 2 SO 4 Dry and concentrate by rotary evaporation to obtain a crude product of dark red oil; the crude product was separated and purified by flash silica gel column chromatography (the mobile phase was a mixture of petroleum ether and ethyl acetate with a volume ratio of 1:1), and dried in vacuo 5 mg of red solid was obtained, which was tripterine derivative b, and the yield was 23%.

[0036] The spectral analysis of the tripterine derivative b is as follows: M.p.142°C; 1 H-NMR (400MHz, CDCl 3 ),δ(ppm):7.04(d,1H,J=6.8Hz,H-6),6.54(s,1H,H-1),6.36(d,1H,J...

Embodiment 3

[0038] The preparation of derivative c (synthetic route such as figure 1 shown)

[0039] Dissolve tripterine (46mg, 0.10mmol) in dichloromethane (3ml), add EDC·HCl (24mg, 0.13mmol), HOBT (17mg, 0.13mmol), ethanolamine (7.9μl, 0.13mmol), stir in ice bath After reacting for 30 min, triethylamine (22 μl) was added, stirred overnight at room temperature, extracted 3 times with dichloromethane, combined organic layers, anhydrous Na 2 SO 4 Dry and concentrate by rotary evaporation to obtain a crude product of a dark red oil; the crude product was separated and purified by flash silica gel column chromatography (the mobile phase was a mixture of petroleum ether and ethyl acetate with a volume ratio of 1:1), and the product was subjected to vacuum After drying, 10 mg of dark red solid was obtained, which was tripterine derivative c, and the yield was 20%.

[0040] The spectral analysis of the tripterine derivative c is as follows: M.p.183°C, 1 H-NMR (400MHz, CDCl 3 ),δ(ppm):6.98(...

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Abstract

The invention discloses a tripterine derivative, biogenetic salt of the derivative, and a preparation method and application of the biogenetic salt. The tripterine has a structure as shown in the specification. The biogenetic salt of the tripterine derivative is prepared by mixing and reacting the tripterine derivative with medicinally acceptable inorganic acid or organic acid. The tripterine derivative and the biogenetic salt of the tripterine derivative can be used for preparing medicines for resisting hepatic fibrosis. A nitrogen-containing hydrophilic group is introduced into C-28 position carboxylic acid and the tripterine derivative is salinized, so that the pharmacokinetic property is improved obviously, the bioavailability is improved, and the safety is improved.

Description

technical field [0001] The present invention relates to a tripterine derivative and a biological salt of the derivative, in particular to a tripterine derivative, the biological salt of the derivative, a preparation method and application thereof. Background technique [0002] Hepatic fibrosis refers to the excessive proliferation and abnormal deposition of extracellular matrix (ECM) components in liver tissue, which will lead to pathological changes in liver structure or function abnormalities. Structurally, hepatic sinusoidal capillarization and fibrosis in hepatic lobule and portal area, Functionally, it can be manifested as decreased liver function and portal hypertension. Hepatic fibrosis is common in most chronic liver diseases of different etiologies, and further development can lead to cirrhosis. my country is a high-prevalence area of ​​hepatitis B virus infection. The estimated annual incidence rate of chronic hepatitis B developing into liver cirrhosis is 2.1%. A...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P1/16
Inventor 汤文建王静史天陆张红童旭臧洪梅
Owner ANHUI MEDICAL UNIV
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