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A kind of use of bakuchiol dihydroflavonoid methyl ether and analogs thereof

A technology of flavone methyl ether of psoraleae and its analogues, which is applied in the field of medicine and can solve the problems of toxic side effects, influence and limitation of clinical application, etc.

Active Publication Date: 2019-05-24
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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  • A kind of use of bakuchiol dihydroflavonoid methyl ether and analogs thereof
  • A kind of use of bakuchiol dihydroflavonoid methyl ether and analogs thereof
  • A kind of use of bakuchiol dihydroflavonoid methyl ether and analogs thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1: Preparation of bakuchiol dihydroflavonoid methyl ether (compound of formula A)

[0040] 10.0kg of Psoraleae medicinal material was extracted with 8 times the volume (80L) of a 95% ethanol aqueous solution, refluxed for 2 hours each time, and refluxed for extraction 3 times in total, combined the extracts, and concentrated under reduced pressure to obtain the extract (about 800mL); 1 times the amount (800mL) of water was added to the extract to suspend, followed by extraction with petroleum ether (1000mL×3) and ethyl acetate (1000mL×3), and the ethyl acetate extract was collected; recovery under reduced pressure Silica gel column chromatography followed by ethyl acetate, followed by gradient elution with petroleum ether and ethyl acetate (10:1-1:5); Elution (9:1-1:1), then use reverse column chromatography methanol-water gradient elution (60% methanol-80% methanol), and finally purify with Sephadex LH-20 (methanol) to obtain formula A Compound, white powder. ...

Embodiment 2

[0045] Example 2: Preparation of compound of formula B

[0046] Dissolve 20 mg of bakuchiol dihydroflavonoid methyl ether [compound of formula A] in 1 mL of pyridine, then add 1 mL of acetic anhydride, leave it at room temperature for 24 h, then add 10 mL of ethyl acetate solvent, back-extract with water, collect the organic phase, concentrate, Sephadex LH-20 column chromatography, the compound of formula B is obtained 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=8.4 Hz, H-2', 6'), 7.70 (1H, s, H-5).

Embodiment 3

[0048] Example 3: Preparation of bakuchiin flavonoid methyl ether (compound of formula C)

[0049]

[0050] Preparation of intermediate of formula 3: 2'-prenyloxy-4'-methoxyacetophenone:

[0051] 500 mg of 2'-hydroxy-4'-methoxyacetophenone (compound of formula 1), 1.25 g of anhydrous potassium carbonate, 15 mL of acetone and 0.4 mL of isopentenyl bromide (compound of formula 2) were added to the reaction flask to make The reaction solution was heated to reflux, and the reaction was incubated at the end of the reaction by TLC monitoring (about 5h of reflux reaction), the reaction solution was cooled to room temperature, extracted with 30 mL of ethyl acetate and 15 mL of water, the ethyl acetate layer was collected, and saturated NaCl solution was used to carry out Washed, dried over anhydrous sodium sulfate, filtered, and the filtrate was purified by silica gel column chromatography and rinsed with ethyl acetate / petroleum ether to obtain the intermediate of formula 3 as a ye...

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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 use of bakuchiol dihydroflavonoid methyl ether and an analog thereof, and belongs to the technical field of medicine. Background technique [0002] Metabolic syndrome is a common disease characterized by abnormal glucose and lipid metabolism, accompanied by increased low-density lipoprotein and decreased high-density lipoprotein cholesterol, and its common diseases are obesity, diabetes, hyperlipidemia and atherosclerosis Sclerosis, among which, diabetic patients are often complicated by hyperlipidemia, cardiovascular disease, diabetic nephropathy, diabetic neuropathy and other diseases. [0003] According to the World Health Organization, more than 220 million people are suffering from diabetes worldwide. Among them, China has become the country with the largest number of diabetics in the world, with a total of 92 million diabetic patients. According to the "New England Journal of Medicine" published on March 25, 2010 Acco...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/352A61K31/353A61P3/08A61P3/06A61P3/10A61P3/04A61P9/10A23L33/10
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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