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3beta-hydroxy-ergosta-5-ene steroid derivative and drug application thereof

A technology of ergosteroids and enosteroids, which is applied in the field of drugs for the prevention or treatment of metabolic syndrome, and achieves an obvious lipid-lowering effect

Active Publication Date: 2019-01-29
MARINE BIOMEDICAL RES INST OF QINGDAO CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(The Journal of Neuroscience, October 30, 2013·33(44):17290–17300) At present, there is no information on the preparation of 3β-hydroxy-ergost-5-ene steroid derivatives for the prevention or treatment of LXRβ-related metabolic syndrome. Reports of new uses in diseases

Method used

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  • 3beta-hydroxy-ergosta-5-ene steroid derivative and drug application thereof
  • 3beta-hydroxy-ergosta-5-ene steroid derivative and drug application thereof
  • 3beta-hydroxy-ergosta-5-ene steroid derivative and drug application thereof

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Experimental program
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Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of compound 1

[0033] (1) Synthesis of intermediate 1-b

[0034] ①Add 89mg of potassium osmate dihydrate, 383mg of pyridine, and 1.14g of N-methyl-N-morpholine oxide into 70ml of dioxane-water (volume ratio: 10:1) mixed solution in sequence, and stir vigorously for about 4 hours. There was an obvious two-phase boundary, and the bottom layer was bright yellow. After cooling down to room temperature, 1.0 g of stigmasterol 1-a was added in batches, and the entire reaction solution was kept at the temperature and continued to stir for 20 h. ②After the reaction, sodium sulfite solution was added, extracted with ethyl acetate, the organic layer was washed successively with potassium hydroxide solution, hydrochloric acid solution, saturated sodium bicarbonate solution and brine, dried and concentrated to obtain the intermediate double hydroxylation product. ③Cool the crude intermediate above to 0°C, add 2.07g NaIO 4 , and the reaction solution wa...

Embodiment 2

[0048] Embodiment 2: the synthesis of compound 2

[0049]

[0050] Compound 1 (38.8mg, 0.1mmol) was dissolved in dry 2ml of dichloromethane, and boron trifluoride ether solution (30.0mg, 0.1mmol) was added at 0°C, then raised to room temperature, and reacted for 2h. After the reaction was completed, water was added to quench and extracted with dichloromethane. The combined organic layers were washed with brine, dried and concentrated. The obtained crude product was purified by column chromatography (30% ethyl acetate / petroleum ether) to obtain compound 2 (22.3 mg, 60%).

[0051] Table 2. The characterization result of embodiment 2 product

[0052]

Embodiment 3

[0053] Embodiment 3: the synthesis of compound 3

[0054]

[0055] Compound 1 (38.8 mg, 0.1 mmol), imidazole (20.4 mg, 0.3 mmol) and tert-butyldimethylsilyl chloride (30 mg, 0.2 mmol) were sequentially added into dichloromethane (5 mL), and stirred at room temperature for 16 h. Washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel flash chromatography (petroleum ether:ethyl acetate=5:1) to obtain compound 3 (35 mg, 70%).

[0056] The characterization result of table 3. embodiment 3 products

[0057]

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PUM

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Abstract

The invention provides a structure of a 3beta-hydroxy-ergosta-5-ene steroid compound, and applications of the compound and the pharmaceutically acceptable form of chemical protection or a prodrug in the preparation of drugs capable of preventing or treating LXRbeta related metabolic syndromes. The LXRbeta related metabolic syndromes include hyperlipidemia, atherosclerosis or hypertension. Throughthe discovery of the evaluation of lipid-lowering activity in animal bodies, the compound has obvious effects on lipid lowering, so that the compound has potentials of further developing into a novellipid-lowering drug.

Description

technical field [0001] The invention belongs to the field of pharmacy, and specifically relates to a class of 3β-hydroxy-ergost-5-ene steroid derivatives and their new application in the preparation of drugs for preventing or treating metabolic syndrome. Background technique [0002] Metabolic syndrome is mostly caused by abnormal metabolism of the human body, and its clinical symptoms are hypertension, hyperglycemia, hyperlipidemia, atherosclerosis and obesity. The pathological basis of metabolic syndrome is abnormal metabolism of sugar, fat and protein. Although it is not directly life-threatening, it can induce other serious life-threatening diseases. According to different targets, clinically used drugs for the treatment of metabolic syndrome are also divided into many types, such as the ACE inhibitor perindopril for lowering blood pressure, and the fibrate drug Libetel for lowering lipids And statins simvastatin, gastrointestinal lipase inhibitor orlistat for weight lo...

Claims

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Application Information

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IPC IPC(8): C07J9/00C07J51/00C07J43/00C07J71/00A61P3/06A61P3/00A61P9/10A61P9/12
CPCC07J9/00C07J43/003C07J51/00C07J71/001
Inventor 徐涛刘红兵蔡兵
Owner MARINE BIOMEDICAL RES INST OF QINGDAO CO LTD
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