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Honokiol derivative as well as preparation method and application

A technology for medicines and compounds, applied in the field of honokiol derivatives and their preparation, can solve the problems of affecting drug efficacy, being insoluble in water, not easily absorbed and utilized, etc., and achieving the effects of good drug efficacy and good solubility

Active Publication Date: 2017-08-29
CHENGDU BIOBEL BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, honokiol is extremely difficult to dissolve in water, and is not easily absorbed and utilized by organisms, which seriously affects its efficacy.

Method used

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  • Honokiol derivative as well as preparation method and application
  • Honokiol derivative as well as preparation method and application
  • Honokiol derivative as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1 prepares honokiol sulfate and salt thereof

[0054] In 50ml of pyridine, add honokiol (cas35354-74-6, molecular weight 266) 10g, pyridine sulfur trioxide complex (cas26412-87-3, molecular weight 159) 17 grams (3 equivalents), stir overnight at room temperature, reduce Concentrate under pressure, add 50ml of dilute acid water, extract three times with 100ml of ethyl acetate, dry the ethyl acetate layer and concentrate to dryness to obtain 10.5 grams of honokiol disulfate as a white solid;

[0055] Add honokiol (cas35354-74-6, molecular weight 266) 10g, triethylamine sulfur trioxide complex (cas761-01-3, molecular weight 181.25) 19.4 grams (3 equivalents) in 50ml pyridine, stir overnight at room temperature , concentrated under reduced pressure, added 50ml dilute acid water, extracted three times with 100ml ethyl acetate, concentrated to dryness after the ethyl acetate layer was dried, and obtained 10.2 grams of honokiol disulfate as a white solid;

[0056] ...

Embodiment 2

[0073] Embodiment 2 prepares honokiol phosphate and salt thereof

[0074] Add honokiol (cas35354-74-6, molecular weight 266) 10g, phosphorus oxychloride (cas10025-87-3, molecular weight 153.33) 23 grams (4 equivalents) in 50ml pyridine, stir overnight at room temperature, concentrate under reduced pressure, Add 50ml of ice water and stir, concentrate under reduced pressure, add 50ml of acetone, a white solid precipitates, and filter to obtain 10.1 grams of honokiol bisphosphate;

[0075] Honokiol bisphosphate: 1 HNMR (300MHz,D 2 O): δ (ppm) 7.21-7.43 (m, 6H) 6.01 (brs, 2H), 4.96-5.07 (m, 4H), 3.33-3.66 (m, 4H);

[0076] ESI-MS m / z:425.2[M-H] - .

[0077] The structural formula of honokiol bisphosphate is as follows:

[0078]

[0079] Add honokiol (cas35354-74-6, molecular weight 266) 10g, phosphorus oxychloride (cas10025-87-3, molecular weight 153.33) 5.8 grams (1 equivalent) in 50ml pyridine, stir overnight at room temperature, concentrate under reduced pressure, Add...

Embodiment 3

[0092] The water solubility test of embodiment 3 honokiol sulfate, phosphoric acid ester and salt thereof

[0093] Detection method: Weigh the test sample ground into fine powder, put it in a certain volume of distilled water at 25°C±2°C, shake vigorously for 30s every 5min, observe the dissolution within 30min, if there are no visible solute particles or droplets, it is considered to be completely dissolved.

[0094] Very soluble means that 1g (ml) of solute can be dissolved in less than 1ml of solvent;

[0095] Soluble means that 1g (ml) of solute can be dissolved in 1 to less than 10ml of solvent;

[0096] Dissolution means that 1 g (ml) of solute can be dissolved in 10 to less than 30 ml of solvent;

[0097] Slightly soluble means that 1g (ml) of solute can be dissolved in 30 to less than 100ml of solvent;

[0098] Slightly soluble means that lg (ml) of solute can be dissolved in 100 to less than 1000ml of solvent;

[0099] Very slightly soluble means that 1 g (ml) of ...

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PUM

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Abstract

The invention discloses a compound shown in formula I: wherein R1 and R2 are selected from H, sulphate or pharmaceutically acceptable salts thereof, and phosphates or pharmaceutically acceptable salts thereof, and R1 and R2 are not simultaneously H. Compared with the honokiol, the novel compound provided by the invention have better solubility in the water, are more advantageous for being prepared into various dosage forms such as tablets and injections, and are easily absorbed and utilized by human body or animal body to have better efficacy. (The molecular formula of composition is described in the description.).

Description

technical field [0001] The invention belongs to the field of chemical medicines, and in particular relates to a honokiol derivative and a preparation method and application thereof. Background technique [0002] Honokiol is an active ingredient contained in magnolia plants or traditional Chinese medicine magnolia bark. It has been used in traditional medicine for a long time. It has a pungent taste and warm nature. Breathing effect. However, honokiol is extremely insoluble in water, and is not easily absorbed and utilized by organisms, which seriously affects its efficacy. Contents of the invention [0003] The object of the present invention is to provide a honokiol derivative and its preparation method and application. [0004] The compound shown in formula I provided by the present invention: [0005] [0006] In the formula, [0007] R 1 , R 2 selected from H, a sulfate ester or a pharmaceutically acceptable salt thereof, a phosphate ester or a pharmaceuticall...

Claims

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Application Information

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IPC IPC(8): C07C305/24C07C303/24C07F9/12A61K31/255A61K31/6615A61P35/00A61P31/04A61P1/04A61P1/02A61P29/00
Inventor 广兵谢建董韧涵廖循秦岭
Owner CHENGDU BIOBEL BIOTECHNOLOGY CO LTD
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