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A kind of methyl gallate analogue and its application

A technology of methyl gallate and analogs, applied in the field of methyl gallate analogs and their synthesis, can solve the problems of limited toxic and side effects, poor patient tolerance, and unclear anti-inflammatory targets

Active Publication Date: 2021-03-16
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, non-steroidal anti-inflammatory drugs in clinical use are mainly organic acids, such as aspirin, indomethacin, and phenylbutazone. These drugs have unclear anti-inflammatory targets, long drug cycles, poor anti-inflammatory effects, Poor patient tolerance and a little toxic side effects are also greatly limited in practical application

Method used

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  • A kind of methyl gallate analogue and its application
  • A kind of methyl gallate analogue and its application
  • A kind of methyl gallate analogue and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of Example 1 Intermediate 2

[0026] 3,4,5-trihydroxybenzoic acid (0.5g, 2.94mmol), 20mL tetrahydrofuran, 3.66g potassium carbonate were added to a 50mL round-bottomed flask, and 4.19mL benzyl bromide was slowly added dropwise under nitrogen protection at 40°C. , the reaction was carried out at a constant temperature of 40 °C for 12 hours, and 20 mL of water was added to the reaction solution to terminate the reaction. Extract three times with chloroform, 20 mL each time, separate the organic phase, wash with water twice, dry with anhydrous MgSO4, evaporate the solvent under reduced pressure on a rotary evaporator, and dissolve the residue in 50% ethanol containing 5mol / L sodium hydroxide. 40 mL of the solution was refluxed at room temperature for 12 hours. After cooling, the pH value was adjusted to 2 with dilute hydrochloric acid. After the precipitation was precipitated, a white solid 2 was obtained by filtration.

Embodiment 2

[0027] Synthesis of Example 2 Intermediates 3a-3f

[0028] Taking the synthesis of 3a as an example, the specific operation is as follows: add 3,4,5-tribenzyloxybenzoic acid (0.3g, 0.7mol), 2-(7-benzotriazole oxide) to a 50mL round-bottom flask -N,N,N',N'-tetramethylurea hexafluorophosphate (0.26g, 0.7mol), 0.2mL N,N'-diisopropylethylamine and 10mL dichloromethane, stirred and refluxed at room temperature for 20 Minutes later, ethylpropylamine (0.06 g, 0.7 mol) was slowly added dropwise from the dropping funnel. After the dropping was completed, stirring was continued at room temperature for 5 hours, and 20 mL of water was added to the reaction solution to terminate the reaction. Extracted twice with ethyl acetate, each 30 mL, separated the organic phase, washed twice with water, anhydrous MgSO 4 After drying, the solvent was evaporated under reduced pressure on a rotary evaporator, and the residue was recrystallized from methanol-water (1:1) solvent system to obtain 0.15 g o...

Embodiment 3

[0029] Example 3 Synthesis of target compounds 4a-4f

[0030] Taking the synthesis of 4a as an example, the specific operation is as follows: in a 50mL round-bottomed flask, add the product 3a (0.29g, 0.6mmol) of the previous step, 12mL methanol-water (1:1v / v) and a catalytic amount of 10% palladium carbon ( 0.1 mmol), hydrogen was passed through under stirring conditions, the reaction was carried out at room temperature for 1 hour, and the reaction solution was filtered under reduced pressure. Methanol was evaporated under reduced pressure on a rotary evaporator, and dichloromethane was slowly added dropwise to the residue until all precipitates were precipitated, and filtered to obtain a gray solid, which was the target compound, 0.04 g, and the yield of compounds 4a-4f was 33.3-46.6 g. %between.

[0031] The product characterization data are as follows:

[0032] 3,4,5-Trihydroxy-N-propylbenzamide(4a)

[0033] Gyay powder, 33.3% yield.m.p:143.8-146.2℃. 1 H NMR (500MHz, D...

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Abstract

The invention discloses a methyl gallate analogue and application thereof. The structure of the methyl gallate analogue is as shown in a formula (I), wherein R is selected from C1 to C6 alkyl groups,N-methyl piperazine substituted C1 to C6 alkyl groups and N-alkyl carbazolyl groups. The methyl gallate analogue disclosed by the invention is capable of better inhibiting the release of inflammatoryfactors of TNF (Tumor Necrosis Factor)-alpha and IL (Interleukin)-6, and particularly, the anti-inflammatory activity of a compound 4e is obviously superior to that of a primer-methyl gallate so thatthe compound has certain anti-inflammatory ability and can be used as a potential anti-inflammatory drug. The formula (I) is shown in the description.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a methyl gallate analog and a synthesis method and application thereof. Background technique [0002] Inflammation is a physiological response of the body to various stimuli such as infection and tissue damage, both acute and chronic. Acute inflammatory responses are often beneficial as part of innate and adaptive immunity. Excessive or uncontrolled inflammatory responses lead to tissue damage. [0003] The use of anti-inflammatory drugs can effectively prevent or treat inflammatory diseases. The existing anti-inflammatory drugs are mainly divided into two categories, namely steroid and non-steroidal anti-inflammatory drugs. Among them, steroid hormone anti-inflammatory drugs have good anti-inflammatory effects. , but it has significant side effects and is not suitable for long-term use. The non-steroidal anti-inflammatory drugs currently in clinical use are mainly organ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/46C07C235/54C07C235/50C07D209/86A61K31/166A61K31/495A61K31/403A61P29/00A61P19/02A61P37/02A61P17/06A61P19/08A61P1/00A61P21/00A61P9/00A61P19/06A61P17/00A61P37/00A61P1/16A61P11/00A61P37/08A61P31/00
CPCA61P1/00A61P1/16A61P9/00A61P11/00A61P17/00A61P17/06A61P19/02A61P19/06A61P19/08A61P21/00A61P29/00A61P31/00A61P37/00A61P37/02A61P37/08C07C235/46C07C235/50C07C235/54C07D209/86
Inventor 刘志国赵云洁钱建畅梁广李校堃
Owner WENZHOU MEDICAL UNIV
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