Leonurine metabolite and preparation method thereof

A technology of leonurine and metabolites, which is applied to the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of the preparation method and activity of the main metabolites of leonurine that have not yet been seen, and achieve good pharmacological activity prospects, Easy to control, cheap and readily available raw materials

Inactive Publication Date: 2016-11-23
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there have been no research reports on the main metabolites of motherurine, its preparation method and activity, etc.

Method used

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  • Leonurine metabolite and preparation method thereof
  • Leonurine metabolite and preparation method thereof
  • Leonurine metabolite and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Synthesis of (2S,3S,4S,5R,6R)-1-methyl-3,4,5,6-tetra-hydroxy-tetrahydro-2H-pyran-2-methyl ester

[0034]

[0035] Add 100 mL of methanol and 0.4 g (0.01 mmol) of sodium hydroxide to a 250 mL flask, stir to dissolve, add 17.6 g (0.1 mmol) of glucuronic acid lactone, stir at room temperature, and add a small amount of sodium hydroxide during this period to keep the reaction solution. pH>8, a total of about 0.6 g of sodium hydroxide was added. After the raw materials were completely dissolved, stirring was continued for 1 h. The reaction solution was yellow and transparent. All methanol was evaporated under reduced pressure to obtain 16.8 g of a yellow syrupy viscous substance. The yield was 16.8 g. 100%.

Embodiment 2

[0037] Synthesis of (2S,3R,4S,5S,6S)-6-(methoxyformyl)tetrahydro-2H-pyran-2,3,4,5-tetra-acetyl-tetra-ethyl ester

[0038]

[0039] In a 250mL flask, add 60mL (0.6mol) acetic anhydride, 11g (0.05mol) compound 2, after dissolving, add dropwise a mixture of perchloric acid and acetic anhydride (0.3mL perchloric acid, 10mL acetic anhydride), control the drop Accelerate so that the temperature of the reaction solution does not exceed 40°C. After the dropwise addition, the reaction is stirred overnight, PE:EA=3:1 system, and separated by silica gel column chromatography to obtain 14.1 g of white solid with a yield of 86%.

Embodiment 3

[0040] Example 3 Synthesis of Compound 4

[0041]

[0042] 15g(0.04mol)(2S,3R,4S,5S,6S)-6-(methoxyformyl)tetrahydro-2H-pyran-2,3,4,5-tetra-acetyl-tetra-ethyl ester Dissolve in 33% HBr acetic acid solution (20 mL) under nitrogen protection, stir at 0 °C for 4 h, add 100 mL of dichloromethane, wash 5 times with ice water and saturated sodium bicarbonate respectively, combine the organic layers, add anhydrous sulfuric acid Dry over sodium and evaporate the solvent to give (2S,3R,4S,5S,6S)-2-bromo-6-(methoxyformyl)tetrahydro-2H-pyran-3,4,5-tri-acetyl- Triethyl ester (compound 3), yield 100%.

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Abstract

The invention belongs to the field of medicine synthesis, and particularly relates to a leonurine main metabolite and a preparation method thereof. The main metabolite which has a structure shown in the formula (I) (please see the formula in the description) and combines leonurine with glucuronic acid is synthesized by taking glucuronic acid lactone, 4-aminobutanol and syringic acid as starting raw materials through multi steps of reactions. The prepared leonurine main metabolite compound which has the novel chemical structure and combines leonurine with glucuronic acid has a good pharmacological activity prospect and can be used for further pharmacological activity evaluation. The method has the advantages that the synthetic route is simple, control is easy, the raw materials are cheap and easy to obtain, and the product stability is good.

Description

technical field [0001] The invention belongs to the field of drug synthesis and relates to leonurine metabolites, in particular to the main metabolites of leonurine and a preparation method thereof. The present invention uses glucuronic acid lactone, 4-aminobutanol and syringic acid as starting materials, and through multi-step reaction, the main metabolite of leonurine combined with glucuronic acid is synthesized. Background technique [0002] The prior art discloses that leonurine has been researched and developed as a national class I new drug candidate drug, and pharmacological studies have shown that it has a good cardioprotective effect. Pharmacokinetic studies have shown that Leonurine is rapidly combined with glucuronic acid and metabolized into Leonurine glucuronic acid complex in vivo. With the in-depth research of Leonurine by researchers in this field, the pharmacological activity and mechanism of action of its metabolites have attracted the attention of researc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00
CPCY02P20/55
Inventor 朱依谆古险峰王莹
Owner FUDAN UNIV
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