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Methyl gallate analogue and application thereof

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

Active Publication Date: 2018-09-14
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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  • Methyl gallate analogue and application thereof
  • Methyl gallate analogue and application thereof
  • Methyl gallate analogue and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1 intermediate 2

[0026] Add 3,4,5-trihydroxybenzoic acid (0.5g, 2.94mmol), 20mL tetrahydrofuran, 3.66g potassium carbonate into a 50mL round-bottomed flask, slowly add 4.19mL benzyl bromide dropwise under nitrogen protection at 40°C, and dropwise , reacted at a constant temperature of 40° C. for 12 hours, and added 20 mL of water to the reaction liquid to terminate the reaction. Extract three times with chloroform, 20 mL each time, separate the organic phase, wash twice with water, dry with anhydrous MgSO4, evaporate the solvent on a rotary evaporator under reduced pressure, and dissolve the residue in 50% ethanol containing 5 mol / L sodium hydroxide The solution was refluxed at room temperature for 12 hours in 40 mL of the solution. After cooling, the pH value was adjusted to 2 with dilute hydrochloric acid. After precipitation, the white solid 2 was obtained by filtration, and the next step of reaction could be carried out directly without...

Embodiment 2

[0027] The synthesis of embodiment 2 intermediate 3a-3f

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

Embodiment 3

[0029] Synthesis of embodiment 3 target compound 4a-4f

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

[0031] 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, DMSO-d 6 )δ:9.02(2H,s,Ar-OH),8.65(...

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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 analogue and its synthesis method and application. 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 steroidal and non-steroidal anti-inflammatory drugs. Although steroidal hormone anti-inflammatory drugs have good anti-inflammatory effects , but has significant side effects and is not suitable for long-term use. Currently, non-steroidal anti-inflammatory drugs in clinical use are mainly organic acids, ...

Claims

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Application Information

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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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