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Hypolipidemic compounds, preparation method thereof and purpose thereof

A technology for reducing blood lipids and compounds, applied in the field of hypolipidemic compounds and their preparation, can solve problems such as minor applications, and achieve the effect of simple process

Inactive Publication Date: 2012-04-04
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The adverse reactions of bile acid sequestrants include nausea, abdominal distension, constipation, diarrhea, intestinal obstruction and other gastrointestinal reactions. Due to the serious gastrointestinal reactions, they are not widely used in clinical practice.

Method used

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  • Hypolipidemic compounds, preparation method thereof and purpose thereof
  • Hypolipidemic compounds, preparation method thereof and purpose thereof
  • Hypolipidemic compounds, preparation method thereof and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Extraction scheme of 2,6-dihydroxybenzoic acid phenylethyl alcohol ester

[0044] 5Kg (dry weight) of the whole plant of Alderwort, crushed, extracted with 95% ethanol (50L×3), concentrated under reduced pressure to obtain 220g of total extract. The total extract was dissolved in 2.0L warm water (about 50°C), extracted with ethyl acetate (1.5L×3) after cooling, and concentrated under reduced pressure to obtain 80g of ethyl acetate. The ethyl acetate fraction was eluted by gradient silica gel column chromatography (CHCl3, CHCl3:CH3OH=50:1, 20:1, 10:1, 5:1, 2:1, CH3OH) and divided into 10 fractions (TLC for detection, The same parts are combined together); Fr2 is separated by silica gel column chromatography (petroleum ether: ethyl acetate=50:1) to obtain 4 small parts, wherein the second small part is obtained by silica gel column chromatography (petroleum ether: chloroform=3 : 1) 70 mg of the target compound was isolated, and spectroscopy and X-single crysta...

Embodiment 2

[0045] Embodiment 2: 2, the synthesis of phenylethyl alcohol ester (2) of 6-dimethoxybenzoate

[0046] Weigh 200mg of 2,6-dimethoxybenzoic acid, place it in a pre-dried round bottom flask, add 10mL of anhydrous CH2Cl2, stir; place the above device in an ice-water bath, and wait for the temperature of the mixture to drop to 0°C, add 250 mg of dicyclohexylcarbodiimide to the mixture, stir for 30 minutes, add 0.122 mL of phenethyl alcohol, 6 mg of 4-N, N-dimethyl-4-aminopyridine, stir at room temperature, TLC Detection, after the reaction is complete, filter directly, and concentrate the mother liquor to obtain a residue, which is separated by silica gel column chromatography (petroleum ether: chloroform = 2: 3) to obtain phenylethyl 2,6-dimethylbenzoate with a yield of 90.6%. Proton NMR spectrum (600MHz, CDCl 3 , δin ppm and TMS as internal standard): δ7.25~7.31(5H, m), 7.22(1H, m), 6.54(2H, d, J=8.2Hz), 4.54(2H, t, J=7.1Hz ), 3.78 (6H, s) and 3.06 (2H, t, J=7.1Hz). C NMR spec...

Embodiment 3

[0047] Embodiment 3: the synthesis of 2-hydroxyl-6-methoxyphenyl ethyl benzoate (3)

[0048] Place the 2,6-dimethylbenzoic acid phenylethyl alcohol ester obtained in the above-mentioned Example 2 in a pre-dried round bottom flask, add 10 mL of anhydrous CH 2 Cl 2 , stirred, and added 1.2 equivalents of AlCl in small amounts in batches 3 , stirred at room temperature, and detected by TLC. After the reaction was complete, the reaction solution was slowly poured into 20 mL of water, extracted and separated to obtain an organic layer, and the organic layer was concentrated to dryness to obtain 2-hydroxyl-6-methoxyphenylbenzoic acid phenylethyl alcohol ester, the obtained compound Without chemical characterization, proceed directly to the next reaction.

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry, and relates to hypolipidemic compounds, a preparation method thereof and a purpose thereof. According to the novel compounds with hypolipidemic activity, a rubiaceae plant geophilaherbacea is adopted as a raw material, and novel 2,6-phenethanol dihydroxybenzoate is obtained by separation and identification through a solvent extraction and chromatography method. According to the invention, substituted aryl acid and substituted aryl alcohol are adopted as raw materials, and are subject to a reaction in an appropriate solvent with the effect of a catalyst under a certain temperature, such that 2,6-phenethanol dihydroxybenzoate and similar substances are produced. The compounds show substantial hypolipidemic effects in hypolipidemic models, and can be used for preparing novel hypolipidemic medicines. The extraction, separation, synthesis and preparation methods disclosed by the invention are advantaged in mild reaction condition, easy operation, and high yield.

Description

[0001] Field [0002] The invention belongs to the technical field of medicinal chemistry, and relates to a class of blood lipid-lowering compounds and a preparation method and application thereof. Background technique [0003] The World Health Organization reports that cardiovascular and cerebrovascular diseases are the main cause of human death. Hypertension, myocardial infarction, cerebral infarction, stroke, etc. caused by hyperlipidemia in my country are increasing at a rate of 12% per year; only stroke patients are nearly 3.5 million per year; 1 / 3 of adults have generally high blood lipids. The death caused by atherosclerosis caused by hyperlipidemia accounts for 75% of the mortality rate of cardiovascular and cerebrovascular diseases, and 80-90% of adults over the age of 30 are found to have symptoms of atherosclerosis, which is an invisible killer of human health. In addition, studies have found that peripheral arterial disease is also a type of coronary heart disease...

Claims

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Application Information

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IPC IPC(8): C07C69/84C07C69/92C07C67/08A61K31/235A61P3/06
Inventor 罗应刚张国林
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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