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A kind of methyl gallate analog 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 problems of undetermined efficacy and function of MG, and achieve the effects of good inhibitory activity and good anti-inflammatory activity.

Active Publication Date: 2022-04-05
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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  • A kind of methyl gallate analog containing amide structure and application
  • A kind of methyl gallate analog containing amide structure and application
  • A kind of methyl gallate analog 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 analog containing an amide structure and its application. The structure of the methyl gallate analog is shown in formula (I). In formula (I), R 1 independently selected from various alkoxy groups, hydroxyl groups, various halogens and aromatic heterocycles. The present invention conducts a large number of experimental studies on a class of methyl gallate analogues with hydrolyzed methyl gallate ester bonds as the mother core structure, and conducts a large number of methyl gallate with hydrolyzed methyl gallate ester bonds as the mother core structure. Analog design, synthesis, and pharmacological activity screening result in a class of methyl gallate analogs with a hydrolyzed methyl gallate ester bond as the mother core structure, and the methyl gallate analogs of the present invention have high-efficiency, broad-spectrum Anti-inflammatory use.

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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Patent Type & Authority Patents(China)
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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