Application of p-dihydroxybenzene farnesyl compounds

A technology of hydroquinone farnesyl compounds, which is applied in the application field of hydroquinone farnesyl compounds, can solve the problems of curative effect failure, anti-tumor chemotherapy curative effect reduction, etc., and achieve reduction in treatment and prevention, cancer prevention or inhibition The effect of tumor cell proliferation

Active Publication Date: 2017-12-29
HANGZHOU BIO SINCERITY PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] 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 p-dihydroxybenzene farnesyl compounds
  • Application of p-dihydroxybenzene farnesyl compounds
  • Application of p-dihydroxybenzene farnesyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The preparation of compound shown in embodiment 1, formula 1-17

[0073] (1) Prepare the extract of Ganoderma lucidum

[0074] 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.

[0075] 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.

[0076] (2) Preparation of compounds

[0077] The LZ-E pr...

Embodiment 2

[0085] The synthesis of compound shown in embodiment 2, formula 3 and formula 4

[0086] For the synthetic route, please refer to literature Yajima, A.; Urao, S.; Katsuta, R.; Nukada, T. Eur. J. Org. Chem.2014, 731-738.

[0087]

[0088] 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% ).

[0089] (E)-3-[2,5-bis(methoxymethoxy)benzene]propenyl acetate (2): to anhydrous solu...

Embodiment 3

[0108] Confirmation of the structure of the compound shown in embodiment 3, formula 1-17

[0109] The 17 prepared compounds were detected by nuclear magnetic resonance, infrared and mass spectrometry to determine the structure of each compound.

[0110] The nuclear magnetic resonance instrument used is BrukerMercury-500 and BrukerMercury-600 megahertz (Bruker Spectrum Instrument Company), the infrared chromatograph is Nicolet IS5FT-IR (U.S. Nicolet Instrument Co., Ltd.), and the mass spectrometer is Bruker APEX III 7.0T and APEX II FT-ICR (Bruker Spectroscopy Instruments).

[0111] It was confirmed that these 17 compounds are all known compounds and have a common hydroquinone farnesyl structure.

[0112] Tables 1 to 8 show the NMR carbon spectrum and hydrogen spectrum confirmation data of each compound.

[0113] 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 acid

[0...

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Abstract

The invention provides an application of p-dihydroxybenzene farnesyl compounds and pharmaceutical salt of p-dihydroxybenzene farnesyl compounds as an alpha-glucosidase, protein-tyrosine-phosphatase IB or HMG-CoA reductase inhibitor, or in preparation of a drug for treating and / or preventing type II diabetes or hyperlipidemia, preparation of a drug or functional healthcare product for reducing blood glucose and blood lipids, preparation of a drug or functional healthcare product for treating or preventing the non-alcoholic fatty liver disease, preparation of a drug or functional healthcare product with the liver protection function and preparation of a drug or functional healthcare product for preventing and / or treating cancer or inhibiting tumor cell proliferation, or as RXR alpha (retinoid X receptor alpha) receptor binding inhibitor, or in preparation of a drug as the RXR alpha receptor binding inhibitor. The inhibitor, drug, food or healthcare product prepared from the p-dihydroxybenzene farnesyl compounds and pharmaceutical salt of the p-dihydroxybenzene farnesyl compounds have no toxic or side effects and have a remarkable treatment effect.

Description

[0001] This application is a divisional application, and its parent case is an invention patent application titled "Application of Hydroquinone Farnesyl Compounds", its application number is 201510578951.1, and its application date is September 11, 2015. The right is 201510217149.X, the priority date is April 30, 2015; 201510294277.4, the priority date is June 2, 2015. technical field [0002] The invention relates to the application field of compounds, in particular to the application of hydroquinone farnesyl compounds. Background technique [0003] 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/343A61K31/192A61K31/34A61K31/575A61K31/155A61P3/10A61P3/06A61P1/16A61P35/00A61P35/02A23L33/00
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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