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
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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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