New depside compounds, preparation method thereof and use

A technology of depacids and compounds, which is applied to a new class of depacids and the field of preparation method and application thereof, can solve the problem that there are not many depacids and the like

Inactive Publication Date: 2008-12-31
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, people's research on depsipates has been limited to extracting and separating them from plants containing such compounds and then studying their biological activities, but there are not many reports on the targeted design and synthesis of depsipates

Method used

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  • New depside compounds, preparation method thereof and use
  • New depside compounds, preparation method thereof and use
  • New depside compounds, preparation method thereof and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment one: the preparation of methyl o-hydroxyphenylacetate

[0020]

[0021] Dissolve o-hydroxyphenylacetic acid (7.6g, 50mmol) in anhydrous methanol (50mL). After it is completely dissolved, slowly add 3ml of 98% concentrated sulfuric acid dropwise at 90°C under stirring, and stop the reaction after reacting under reflux for 24 hours. . After cooling, add 100mL of water, then extract with ethyl acetate, wash the organic layer twice with saturated brine, then wash with anhydrous Na 2 SO 4 After drying, the solvent was evaporated to dryness under reduced pressure and then separated with a silica gel column. Elution with ethyl acetate:petroleum ether=1:5 gave the target compound. White powder, yield 90%, mp: 61~62℃, 1 H NMR (300MHz, d 6 -DMSO): 3.54 (s, 2H); 3.58 (s, 3H); 6.78 (m, 2H); 7.06 (m, 2H); 9.47 (s, 1H). 13 C NMR (DMSO-d6, δppm): 171.9, 155.5, 131.2, 128.2, 121.4, 118.9, 115.0, 51.6, 35.2. MS (ESI): 167.1 (C 9 h 11 o 3 ,[M+H] + ).Anal.Calcd for...

Embodiment 2

[0022] Embodiment two: the preparation of ethyl o-hydroxyphenylacetate

[0023]

[0024] Dissolve o-hydroxyphenylacetic acid (7.6g, 50mmol) in absolute ethanol (50mL), and after it is completely dissolved, slowly add 3.5ml of 98% concentrated sulfuric acid dropwise under stirring at 95°C, and stop the reaction after 24 hours under reflux reaction. After cooling, add 100mL of water, then extract with ethyl acetate, wash the organic layer twice with saturated brine, then wash with anhydrous Na 2 SO 4 After drying, the solvent was evaporated to dryness under reduced pressure, separated by silica gel column, and eluted with ethyl acetate:petroleum ether=1:4.5 to obtain the target compound as a white powder. Yield 86%, mp: 67~68℃; 1 H NMR (300MHz, d 6 -DMSO): 1.17 (t, J = 7.1 Hz, 3H); 3.53 (s, 2H); 4.01 (m, 2H); 6.75 (m, 2H); 7.07 (m, 2H); 9.46 (s, 1H) . 13 C NMR (DMSO-d6, δppm): 171.6, 155.3, 131.8, 127.9, 121.8, 118.3, 115.4, 51.5, 35.8, 14.3. MS (ESI): 181.1 (C 10 h 1...

Embodiment 3

[0025] Example 3: Preparation of 4-fluorophenylacetic acid-2-(methoxycarbonylmethyl)phenol ester (compound 1).

[0026]

[0027] The product methyl o-hydroxyphenylacetate (1.66g, 10mmol) obtained in Example 1 was dissolved in anhydrous dichloromethane (50mL), and after being completely dissolved, 4-fluorophenylacetic acid ( 1.85 g, 12 mmol). Then add N,N-dimethylaminopyridine (DMAP) (248mg, 2.03mmol) and N,N-dicyclohexylcarbodiimide (DCC) (2.26g, 11mmol), and stir under reflux for 12 hours to stop the reaction . After being completely cooled, add 100mL of water, then extract with ethyl acetate, wash the organic layer twice with saturated brine, and then wash with anhydrous Na 2 SO 4 After drying, the solvent was evaporated to dryness under reduced pressure and then separated with a silica gel column, eluting with ethyl acetate:petroleum ether=1:5 to obtain the target compound as a light yellow oil. Yield 89%, 1 HNMR (300MHz, d 6 -DMSO): 3.54 (s, 2H); 3.55 (s, 3H); 3.95 ...

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Abstract

Disclosed is a class of depside compounds as shown in the right general formula, wherein, R1 is equal to -CH3or-CH2CH3; R2 is equal to H, F, Cl or Br; R3 is equal to H, Cl, Br, OCH3, OCH2CH3 or NO2; R4 is equal to H, F, Cl, Br, OCH3, OCH2CH3 or CH3; R5 is equal to H or OCH3; n is equal to 0 or 1. The depside compounds of the invention can inhibit Gram-positive strains, while some of the depside compounds can inhibit Gram-negative strains, which are not reported in the previous literature. The invention also enables the selected compounds with good antibacterial activity to go through the test in inhibiting the IL-8 production amount caused by bacteria, while the result shows that one of the compounds has strong inhibition to IL-8 caused by the stimulation of escherichia coli, so the compound has the potential to join a class of non-steroidal anti-inflammatory drugs.

Description

technical field [0001] The invention relates to a preparation method and application of a novel class of depsipated phenolic acid compounds. Background technique [0002] Depsipolic acid, in a strict sense, refers to the compound formed by connecting two or more benzene rings with the participation of ester bonds formed by phenolic hydroxyl groups. Natural depsipates are mainly found in mosses, but higher plants such as heather shrubs and poppies also contain such compounds. It is reported that some depsipphenolic acid compounds isolated from bryophytes have many biological activities, including activities against mycobacteria, Gram-positive bacteria, insects and nematodes. In addition, they also exhibit anti-cell proliferation, anti-cancer, anti-HIV-1 integrase, anti-virus, and antipyretic and analgesic effects. There are also studies that show that some depsipates can become non-steroidal anti-inflammatory drugs by inhibiting the biosynthesis of prostaglandins and leukot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/66C07C69/734C07C67/08A61K31/216A61P29/00A61P31/04
CPCY02A50/30
Inventor 朱海亮吕鹏程宋忠诚
Owner NANJING UNIV
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