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Application of hydroquinone farnesyl group compound

A technology for hydroquinone farnesyl compounds, which is applied to the application field of hydroquinone farnesyl compounds, can solve the problems of ineffectiveness of curative effect, decreased curative effect of anti-tumor chemotherapy, etc., so as to reduce treatment and prevention, prevent cancer or inhibit The effect of tumor cell proliferation

Active Publication Date: 2016-01-06
HANGZHOU BIO SINCERITY PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] Due to the continuous emergence of toxicity, side effects and drug resistance of traditional chemotherapy drugs, the efficacy of anti-tumor chemotherapy is reduced or invalid. Therefore, it is imminent to find new anti-tumor drugs.

Method used

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  • Application of hydroquinone farnesyl group compound
  • Application of hydroquinone farnesyl group compound
  • Application of hydroquinone farnesyl group compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] The preparation of compound shown in embodiment 1, formula 1-17

[0072] (1) Prepare the extract of Ganoderma lucidum

[0073] Ganoderma lucidum fruiting body is cut into pieces, weighing 5000 grams. Reflux extraction with 15L aqueous solution of 95% ethanol by volume for 3 times, 1 hour each time. The extracts were combined, concentrated and dried under reduced pressure to obtain 170 g of extract.

[0074] The extract was further dissolved with 600 ml of distilled water, extracted three times with an equal volume of n-hexane, and the organic phase was discarded. The aqueous phase was extracted three times with an equal volume of ethyl acetate, the aqueous phase was discarded, and the ethyl acetate extracts were combined. Evaporate ethyl acetate to dryness with a rotary evaporator (RE-52AA, purchased from Shanghai Yarong Biochemical Instrument Factory) to obtain 54 g of extract, which is designated as LZ-E.

[0075] (2) Preparation of compounds

[0076] The LZ-E pr...

Embodiment 2

[0084] The synthesis of compound shown in embodiment 2, formula 3 and formula 4

[0085] For the synthetic route, please refer to literature Yajima, A.; Urao, S.; Katsuta, R.; Nukada, T. Eur. J. Org. Chem.2014, 731-738.

[0086]

[0087] 2,5-bis(methoxymethoxy)benzaldehyde (1): 2,5-dihydroxybenzaldehyde (400mg, 2.90mmol) cooled to 0°C, potassium carbonate (4.09g, 29.0mmol) Chloromethyl methyl ether (689uL, 8.70mmol) was added to the acetone solution (60ml), and stirred at room temperature for 10 hours. Diluted with water (60ml) followed by extraction three times with ethyl acetate (60ml), the combined organic layers were extracted with water and brine, dried over sodium sulfate. After vacuum concentration, the extract was purified by silica gel column chromatography (n-hexane / ethyl acetate, 3:1) to obtain a colorless oily substance 2,5-bis(methoxymethoxy)benzaldehyde (1) (642mg, 98% ).

[0088] (E)-3-[2,5-bis(methoxymethoxy)benzene]propenyl acetate (2): to anhydrous solu...

Embodiment 3

[0107] Confirmation of the structure of the compound shown in embodiment 3, formula 1-17

[0108] The 17 prepared compounds were detected by nuclear magnetic resonance, infrared and mass spectrometry to determine the structure of each compound.

[0109] Wherein the nuclear magnetic resonance instrument used is BrukerMercury-500 and BrukerMercury-600 megahertz (Bruker Spectrum Instrument Company), the infrared chromatograph is NicoletIS5FT-IR (U.S. Nikolai Instrument Co., Ltd.), and the mass spectrometer is BrukerAPEXIII7.0T and APEXIIFT-ICR (Bruker Spectroscopy Instruments Inc.).

[0110] It was confirmed that these 17 compounds are all known compounds and have a common hydroquinone farnesyl structure.

[0111] Tables 1 to 8 show the NMR carbon spectrum and hydrogen spectrum confirmation data of each compound.

[0112] Compound 1: [(E)-2-(5-Hydroxybenzofuran-2-yl)-6,10-dimethyltetradecane-5,9-geranic acid](E)-2-(5 -hydroxybenzofuran-2-yl)-6,10-dimethylundeca-5,9-dienoic aci...

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Abstract

The invention provides a hydroquinone farnesyl group compound and application of a pharmaceutical salt thereof in serving as an alpha-glucosidase, protein-tyrosine-phosphatase 1B or HMG-CoA reductase inhibitor, or in preparing drug for treating and / or preventing type-II diabetes or hyperlipidemia, or in preparing drug or functional healthcare products having hypoglycemic and hypolipidemic functions, or in preparing drug or functional healthcare products having a function of treating or preventing non-alcoholic fatty liver disease, or in preparing drug or functional healthcare products having liver protection effect, or in preparing drug or functional healthcare products for preventing and / or treating cancer or inhibiting tumor cell proliferation, or in serving as an RXRalpha receptor binding inhibitor, or in preparing drug serving as the RXRalpha receptor binding inhibitor. The inhibitors, the drug, food or the healthcare products prepared through the hydroquinone farnesyl group compound and the pharmaceutical salt are free of toxic and side effect and remarkable in treatment effect.

Description

technical field [0001] The invention relates to the application field of compounds, in particular to the application of hydroquinone farnesyl compounds. Background technique [0002] With the development of society, the continuous improvement of people's living standards and the adjustment of diet structure, the diet tends to be surplus, which leads to the continuous increase of the incidence of metabolic diseases, among which hyperglycemia and hyperlipidemia attract the most attention. At present, diabetes all over the world The number is about 200 million, and it is increasing every year at an astonishing rate. The number of diabetics in China is 40 million, accounting for 1 / 5 of the total number of diabetics in the world. In addition, the incidence of cardiovascular diseases such as atherosclerosis and coronary heart disease caused by elevated blood lipids has increased year by year, and has a younger trend. Hypoglycemic and hypolipidemic drugs have become one of the fo...

Claims

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Application Information

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IPC IPC(8): A61K31/343A61K31/192A61K31/365A61K31/56A61K31/575A61P35/00A61P35/02A61P3/10A61P3/06A61P1/16A23L1/30
CPCA23V2002/00A61K31/155A61K31/192A61K31/34A61K31/343A61K31/575A23L33/00A61K2300/00A23V2200/30A23V2200/3262A23V2200/328A23V2200/308
Inventor 刘宏伟汪锴宝丽韩俊杰
Owner HANGZHOU BIO SINCERITY PHARMA TECH CO LTD
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