Application of bavachinin and analogs of bavachinin

A technology of bakuchiol dihydroflavonoid methyl ether and analogs, which can be applied in the field of medicine and can solve the problems of affecting and limiting clinical application, toxic and side effects, and the like

Active Publication Date: 2016-10-05
SHANGHAI UNIV OF T C M
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, research on peroxisome proliferator-activated receptor PPARα / γ agonists has recently become a hot spot, and PPARγ agonists-thiazolidines (TZDs) have been used as drugs, such as: rosiglitazone, Biglitazone, etc., PPARα agonist-fibrate drugs, such as: fenofibric acid, etc.; existing studies have shown that although the above drugs have obvious PPARγ or PPARα agonistic activity and can be used as drugs for the treatment of metabolic syndrome, their At the same time, it has obvious toxic side effects (such as edema, liver toxicity, heart failure and bladder cancer), which affect and limit their clinical application
[0005] Psoralen dihydroflavone methyl ether (bavachinin) is the active ingredient of commonly used traditional Chinese medicine psoralen, its CAS number is: 19879-30-2, and its molecular formula is: C 21 h 22 o 4 , the molecular weight is: 338.4, and the chemical structural formula is: Existing studies have shown that the compound has various biological and pharmacological activities such as anti-oxidation, anti-bacteria, anti-fungal, anti-inflammatory, anti-tumor, antipyretic, pain relief, etc. Related use reports of analogs that can enhance the agonistic activity of PPARα or / and PPARγ

Method used

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  • Application of bavachinin and analogs of bavachinin
  • Application of bavachinin and analogs of bavachinin
  • Application of bavachinin and analogs of bavachinin

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Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of psoralen dihydroflavone methyl ether (compound of formula A)

[0040] 10.0kg of psoralen medicinal material was reflux extracted with 8 times the volume (80L) of 95% ethanol aqueous solution, refluxed for 2 hours each time, and refluxed for 3 times, the combined extracts were concentrated under reduced pressure to obtain the extract (approx. 800mL); add 1 times the amount (800mL) of water to the extract to suspend, then extract with petroleum ether (1000mL×3) and ethyl acetate (1000mL×3) successively, collect the ethyl acetate extract; recover under reduced pressure Carry out silica gel column chromatography after ethyl acetate, carry out gradient elution with petroleum ether and ethyl acetate successively (10:1-1:5); Use silica gel column chromatography of obtained fraction: use cyclohexane-acetone gradient first Elution (9:1-1:1), then use reverse column chromatography methanol-water gradient elution (60% methanol-80% methanol), and fi...

Embodiment 2

[0045] Embodiment 2: the preparation of formula B compound

[0046] Dissolve 20mg of psoralen dihydroflavone methyl ether [compound of formula A] in 1mL of pyridine, then add 1mL of acetic anhydride, let stand at room temperature for 24h, then add 10mL of ethyl acetate solvent, back-extract with water, collect the organic phase, concentrate, SephadexLH -20 column chromatography to obtain the compound of formula B as white powder.

[0047] 1 H-NMR (CDCl 3 ,400MHz)δ:1.72(3H,s,CH3-5″),1.76(3H,s,CH3-4″),2.35(3H,s,CH3CO),2.83(1H,dd,J=2.8,16.8Hz ,H-3),3.04(1H,dd,J=13.2,16.8Hz,H-3),3.27(2H,d,J=7.2Hz,H-1″),3.88(3H,s,OCH3), 5.29(1H,m,H-2″),5.47(1H,dd,J=2.8,13.2Hz,H-2),6.47(1H,s,H-8),7.18(2H,d,J=8.4 Hz, H-3', 5'), 7.52 (2H, d, J=8.4Hz, H-2', 6'), 7.70 (1H, s, H-5).

Embodiment 3

[0048] Embodiment 3: the preparation of psoralen flavone methyl ether (compound of formula C)

[0049]

[0050] Formula 3 intermediate: preparation of 2'-isopentenyloxy-4'-methoxyacetophenone:

[0051] Add 500mg of 2'-hydroxy-4'-methoxyacetophenone (compound of formula 1), 1.25g of anhydrous potassium carbonate, 15mL of acetone and 0.4mL of prenyl bromide (compound of formula 2) into the reaction flask, and make The temperature of the reaction solution was raised to reflux, and the heat preservation reaction was carried out; when the reaction was monitored by TLC (about 5 hours of reflux reaction), the reaction solution was cooled to room temperature, extracted with 30 mL of ethyl acetate and 15 mL of water, and the ethyl acetate layer was collected and carried out with saturated NaCl solution. After washing, drying over anhydrous sodium sulfate, and filtering, the filtrate was purified by silica gel column chromatography and rinsed with ethyl acetate / petroleum ether to obt...

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Abstract

The invention discloses application of bavachinin and analogs of bavachinin. According to the application, bavachinin or/and analogs of bavachinin serve as active ingredients to prepare compositions for enhancing exciting activity of PPARalpha or/and PPARgamma. Research results show that bavachinin and analogs of bavachinin can remarkably improve the transcriptional activity of a PPARgamma exciting agent to PPARgamma, enhance the transcriptional activity of a PPARalpha exciting agent to PPARalpha and serve as active ingredients of PPARalpha or/and PPARgamma exciting agents to prepare compositions for preventing or treating the metabolic syndrome, the application range of bavachinin and analogs of bavachinin can be widened, and decrement and synergism of PARalpha or/and PPARgamma exciting agents can be achieved to reduce the toxic and side effects of PARalpha or/and PPARgamma exciting agents and achieve wide clinical application of PARalpha or/and PPARgamma exciting agents.

Description

technical field [0001] The invention relates to the application of psoralen dihydroflavone methyl ether and its analogues, belonging to the technical field of medicine. Background technique [0002] Metabolic syndrome is a common disease characterized by abnormal glucose and lipid metabolism, accompanied by elevated low-density lipoprotein and low high-density lipoprotein cholesterol. The common symptoms are obesity, diabetes, hyperlipidemia and atherosclerosis Among them, diabetic patients often have hyperlipidemia, cardiovascular disease, diabetic nephropathy, diabetic neuropathy and other diseases. [0003] According to the World Health Organization, more than 220 million people worldwide suffer from diabetes. Among them, China has become the country with the largest number of diabetics in the world, with a total of 92 million diabetics. According to the "New England Journal of Medicine" published on March 25, 2010 According to the data of the research report, there are c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/352A61K31/353A61P3/08A61P3/06A61P3/10A61P3/04A61P9/10A23L1/30
Inventor 李医明黄诚冯丽郭夫江杜国新朱维良李波陈凯先
Owner SHANGHAI UNIV OF T C M
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