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Puerarin derivative and its medicinal use

A technology of puerarin derivatives and halogens, applied in the directions of sugar derivatives, sugar derivatives, drug combinations, etc., can solve problems such as unfavorable crossing of the blood-brain barrier, patient inconvenience, tissue necrosis, etc.

Inactive Publication Date: 2007-04-11
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the polyhydroxy chemical structure of puerarin determines its poor fat solubility and low bioavailability. At present, it is mainly administered in the form of injection. For long-term cardiovascular and cerebrovascular chronic diseases, long-term injection not only brings inconvenience to patients, but even causes local damage. Tissue necrosis or infection, increasing patient suffering
Although some tablets, capsules, and granules have appeared, puerarin is poorly absorbed in the gastrointestinal tract and has low bioavailability after oral administration
Moreover, the polyhydroxy structure of puerarin is not conducive to crossing the blood-brain barrier, which affects the curative effect on cerebrovascular diseases

Method used

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  • Puerarin derivative and its medicinal use
  • Puerarin derivative and its medicinal use
  • Puerarin derivative and its medicinal use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1.7-O-pivaloyl puerarin

[0051]

[0052]0.416 g (1 mmol) of puerarin was dissolved in 50 ml of acetone, 0.414 g (3 mmol) of anhydrous potassium carbonate was added, and 1 mmol of pivaloyl chloride was added dropwise under stirring at room temperature, and the reaction was tracked by TLC. Stir until the raw material point disappears, spin off most of the solvent, add ethyl acetate to extract, wash with water, dry over anhydrous sodium sulfate, spin off the solvent, column chromatography (ethyl acetate: methanol = 10: 1) to obtain 0.345 g of a white solid product , melting point: 216-218°C, yield 69%.

[0053] 1 H NMR (300MHZ, CD 3 OD), δ: 8.261 (S, 3 / 7H, H2), 8.246 (S, 4 / 7H, H2), 8.17 (d, 1H, H5), 7.35 (d, 2H, H2'6'), 7.165 ( d, 3 / 7H, H6), 7.095 (d, 4 / 7H, H6), 6.80 (d, 2H, H3'5'), 1.37 (S, 9H, -CH 3 ), 5.05(d, 4 / 7H, H9), 4.66(d, 3 / 7H, H9), 4.16(t, 3 / 7H, H14), 3.94(t, 4 / 7H, H14), 3.83(d, 1H, H15), 3.64 (dd, 3 / 7H, H15), 3.54 (dd, 4 / 7H, H15), 3.22-3.52 (m, ...

Embodiment 2

[0054] Example 2.7-O-acetyl puerarin

[0055]

[0056] Dissolve 0.416 g (1 mmol) of puerarin in 50 ml of acetone, add 0.414 g (3 mmol) of anhydrous potassium carbonate, add 1 mmol of acetyl chloride dropwise under stirring at room temperature, follow the reaction by TLC, and stir at room temperature When the raw material point disappeared, most of the solvent was spun off, ethyl acetate was added for extraction, washed with water, dried over anhydrous sodium sulfate, the solvent was spun off, and column chromatography (ethyl acetate:methanol=10:1) gave 0.289 g of a white solid product. Melting point: 194-196°C, yield 63%.

[0057] 1 H NMR (300MHz, CD 3 OD), δ: 8.278 (S, 2 / 5H, H2), 8.246 (S, 3 / 5H, H2), 8.18 (d, 1H, H5), 7.36 (d, 2H, H2'6'), 7.175 ( d, 2 / 5H, H6), 7.15 (d, 3 / 5H, H6), 6.80 (d, 2H, H3'5'), 1.37 (S, 9H, -CH 3 ), 5.05(d, 3 / 5H, H9), 4.67(d, 2 / 5H, H9), 4.15(t, 2 / 5H, H14), 3.93(t, 3 / 5H, H14), 3.83(d, 1H, H15), 3.64 (dd, 2 / 5H, H15), 3.54 (dd, 3 / 5H, H15), 3.3-3.5 ...

Embodiment 3

[0058] Example 3.7-O, 4'-O-dipivaloyl puerarin

[0059]

[0060] Dissolve 0.416 g (1 mmol) of puerarin in 50 ml of acetone, add 0.414 g (3 mmol) of anhydrous potassium carbonate, add dropwise two mmoles of pivaloyl chloride under stirring at room temperature, follow the reaction by TLC, and Stir until the raw material point disappears, spin off most of the solvent, add ethyl acetate to extract, wash with water, dry over anhydrous sodium sulfate, spin off the solvent, column chromatography (ethyl acetate: methanol = 10: 1) to obtain 0.42 g of a white solid product . Melting point: 163-165°C, yield 71%.

[0061] 1 H NMR (300MHz, CDCl 3 ), δ: 8.01 (S, 2 / 3H, H2), 7.99 (S, 1 / 3H, H2), 8.31 (d, 1H, H5), 7.41 (d, 2 / 3H, H2'6'), 7.39 (d, 4 / 3H, H2'6'), 7.11(d, 1 / 3H, H6), 7.02(d, 2 / 3H, H6), 6.85(d, 2H, H3'5'), 5.28(d , 2 / 3H, H9), 4.83(d, 1 / 3H, H9), 5.62(dd, 1 / 3H, H14), 5.39(dd, 2 / 3H, H14), 3.40-4.20(m, 5H, H11 , H12, H13, H15).0.80-1.50(m, 18H, CH 3 ).

[0062] MS (FAB): M+1 = ...

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Abstract

The present invention discloses the puerarin derivatives, and their preparation process, medicine compositions and application in preparing medicine for treating cardiac and cerebral vascular diseases, obstruction of retinal artery and vein, sudden hearing loss and other diseases, improving memory and lowering blood sugar.

Description

technical field [0001] The present invention relates to a new puerarin derivative represented by general formula (I), its preparation method, a pharmaceutical composition containing one or more components of these compounds, and the use of such compounds in the preparation of diseases related to cardio-cerebral circulation, and retinal Arteriovenous obstruction, sudden deafness and other diseases and the application of drugs for improving memory and lowering blood sugar. Background technique [0002] Puerarin is an isoflavone glucoside extracted from the dried roots of the leguminous plants Pueraria lobata (Willd.) Ohwi and P. thomaonii Benth. The chemical name is 74'- Dihydroxy-8-β-D-glucosyl isoflavone is one of the main active ingredients in Pueraria lobata, a traditional Chinese medicine, and has a wide range of pharmacological effects. Studies have shown that puerarin has a dilating effect on coronary arteries, can protect global ischemic myocardium and myocardial isch...

Claims

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Application Information

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IPC IPC(8): C07H7/06C07H13/06A61K31/7048A61P9/00A61P27/16A61P25/28A61P3/10
Inventor 冯志强郭宗儒褚凤鸣孙飘扬周云曙袁开红
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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