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Methyl gallate analogue containing amide structure and application

A technology for methyl gallate and analogs, which is applied in the field of methyl gallate analogs and their preparation, can solve the problem that the efficacy and function of MG are not yet determined, and achieve the effects of good inhibitory activity and good anti-inflammatory activity.

Active Publication Date: 2018-11-23
WENZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although methyl gallate (MG) has been shown to be beneficial in a variety of inflammatory diseases, the potency and function of MG in ALI have not been established

Method used

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  • Methyl gallate analogue containing amide structure and application
  • Methyl gallate analogue containing amide structure and application
  • Methyl gallate analogue containing amide structure and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The chemical structure characterization data of the compound 4a synthesized in Example 1

[0046] Compound (4a): 3,4,5-Trihydroxy-N-phenylbenzamide

[0047] 3,4,5-trihydroxy-N-phenylbenzamide

[0048] White powder, yield: 48.8%, melting point: 203.6-206.0.3°C. 1 H NMR (500MHz, DMSO-d 6 )δ: 9.90 (1H, s, Ar-NH), 9.08 (3H, s, Ar-OH), 7.74 (2H, d, J=7.864Hz, ArH 2 ), 7.31 (2H, t, J=7.830Hz, ArH 2 ), 7.05 (1H, t, J=7.351Hz, ArH), 6.95 (2H, s, ArH 2 ). 13 C NMR (125MHz, DMSO-d 6 )δ(ppm): 165.54, 145.44×2, 139.55, 136.71, 128.43×2, 124.99, 123.06, 120.09×2, 107.15×2. ESI-MS m / z: 246.09(M+H) + .Such as figure 1 Shown is the chemical structure of a class of methyl gallate analogues synthesized by the present invention with the hydrolyzed methyl gallate ester bond as the core structure.

Embodiment 2

[0049] The chemical structure characterization data of the compound 4b synthesized in Example 2

[0050] Compound (4b): N-(4-ethoxyphenyl)-3,4,5-trihydroxybenzamideN-(4-ethoxyphenyl)-3,4,5-trihydroxybenzamide

[0051] White powder, yield: 44.7%, melting point: 191.2-194.1°C. 11 H NMR (500MHz, DMSO-d 6 )δ: 9.76 (1H, s, Ar-NH), 9.13 (2H, s, Ar-OH), 8.79 (1H, s, Ar-OH), 7.61 (2H, d, J=8.429Hz, ArH 2 ),6.92(2H,s,ArH 2 ), 6.86 (2H, d, J=8.439Hz, ArH 2 ),3.98-3.95(2H,m,Ar-OCH 2 -), 1.31 (3H, t, J=6.640Hz, Ar-OCH 2 -CH 3 ). 13 C NMR (125MHz, DMSO-d 6 )δ(ppm): 165.12, 154.37, 145.41×2, 136.48, 132.54, 125.14, 121.64×2, 114.08×2, 107.02×2, 62.99, 14.67. ESI-MS m / z: 290.10(M+H) + .Such as figure 1 Shown is the chemical structure of a class of methyl gallate analogues synthesized by the present invention with the hydrolyzed methyl gallate ester bond as the core structure.

Embodiment 3

[0052] The chemical structure characterization data of the compound 4c synthesized in embodiment 3

[0053] Compound (4c): N-(3,5-dimethoxyphenyl)-3,4,5-trihydroxybenzamide

[0054] N-(3,5-dimethoxyphenyl)-3,4,5-trihydroxybenzamide

[0055] Gray powder, yield: 49.3%, melting point: 129.7-131.8°C. 1 H NMR (500MHz, DMSO-d 6 )δ: 9.81 (1H, s, Ar-NH), 9.19 (3H, s, Ar-OH), 7.07 (2H, d, ArH 2 ),6.93(2H,s,ArH 2 ), 6.21(1H, t, J=2.008Hz, ArH), 3.71(6H, s, Ar-OCH 3 ). 13 C NMR (125MHz, DMSO-d 6 )δ(ppm): 165.56, 160.25×2, 145.44×2, 141.25, 136.78, 124.92, 107.13×2, 98.20×2, 95.15, 55.00×2. ESI-MS m / z: 306.05(M+H) + .Such as figure 1 Shown is the chemical structure of a class of methyl gallate analogues synthesized by the present invention with the hydrolyzed methyl gallate ester bond as the core structure.

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Abstract

The invention discloses a methyl gallate analogue containing an amide structure and application. The structure of the methyl gallate analogue is shown as a formula (I); in the formula (I), R1 is independently selected from various alkoxy, hydroxyl, various halogens and aromatic heterocycles. The invention does a lot of experiment researches aiming at the technical field of a methyl gallate analogue which takes a hydrolyzed methyl gallate ester bond as a parent nucleus structure, and a lot of design, synthesis and pharmacological activity screening of the methyl gallate analogue which takes thehydrolyzed methyl gallate ester bond as the parent nucleus structure are carried out to obtain one type of the methyl gallate analogue which takes the hydrolyzed methyl gallate ester bond as the parent nucleus structure; the methyl gallate analogue provided by the invention has high-efficiency and broad-spectrum anti-inflammatory application. The formula I is shown in the description.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a methyl gallate analogue containing an amide structure and a preparation method and application thereof. Background technique [0002] As an important pathological process, inflammation is very common in the human body, and it itself is an autoimmune response of the body to external or foreign body stimuli. And when this response is dysregulated or excessively responds to the body's self-injury, it evolves into inflammation. Therefore, most diseases are accompanied by the mediation and occurrence of inflammation, and the mediation and occurrence of inflammation aggravate the damage to the body of the disease, such as acute lung injury, rheumatoid arthritis, diabetes complications, cancer, atherosclerosis sclerosis, inflammatory bowel disease, etc. In these processes, proinflammatory factors such as TNF-α, IL-6, IL-1β, etc. have played an important role. At prese...

Claims

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Application Information

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IPC IPC(8): C07D209/08C07D295/135C07D209/42C07D209/18C07D213/81C07D333/38C07D277/56A61P19/02A61P29/00A61P19/08A61P1/00A61P19/06A61P25/00A61K31/44A61K31/404A61K31/495A61K31/5375A61K31/381A61K31/426A61K31/40
CPCA61P1/00A61P19/02A61P19/06A61P19/08A61P25/00A61P29/00C07D209/08C07D209/18C07D209/42C07D213/81C07D277/56C07D295/135C07D333/38C07C2602/08
Inventor 刘志国张健钱建畅张亚利赵云洁梁广
Owner WENZHOU MEDICAL UNIV
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