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Phenol AB ring structure compound and preparation method and application thereof

A compound and phenol technology, applied in the field of phenol AB ring structure compounds and their preparation, can solve the problems of few types of polyphenol compounds, low activity and the like, and achieves simple process, easy realization, good anti-influenza virus neuraminic acid The effect of enzymatic activity

Active Publication Date: 2020-05-29
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

For example, tea polyphenols are consistent with influenza neuraminidase and influenza-infected cells in vitro, and bitter tea extract has a good lung index inhibition rate for mice infected with H9N2 influenza virus strains; Gao Zengping’s research team will The isolated 12 polyphenolic compounds and the neuraminidase in influenza and the verification of the target compound by the cytopathic pathology (CPE) method reached a basically consistent conclusion, all of which can better inhibit the influenza virus (Mianma Guanzhong Anti-influenza virus activity screening of phloroglucinol compounds [J]. Chinese Herbal Medicine, 2018, 49(2): 305-312, Liu Chang, etc.), but there are few types of polyphenolic compounds against influenza virus in the prior art , the problem of low activity

Method used

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  • Phenol AB ring structure compound and preparation method and application thereof
  • Phenol AB ring structure compound and preparation method and application thereof
  • Phenol AB ring structure compound and preparation method and application thereof

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preparation example Construction

[0034] The present invention also provides that the phenolic AB ring structure compound has the structure shown in formula I and R 1 The preparation method when being 1-1, 1-2 or 1-3, comprises the following steps:

[0035] 2,4,6-trihydroxyacetophenone is subjected to condensation reaction with compound 1 to obtain 1 It is a phenolic AB ring structure compound of 1-1, 1-2 or 1-3, and the compound 1 is p-aminobenzoic acid, 2-hydroxyl-4-aminobenzoic acid or 3-methyl-4-aminobenzoic acid . In the present invention, the condensation reaction is preferably carried out under the conditions of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide) and 4-dimethylaminopyridine.

[0036] In a specific embodiment of the present invention, it is preferred to mix 1.2 equivalents of p-aminobenzoic acid (4.28 mmol, 587.22 mg), 1.5 equivalents of EDAC (1-(3-dimethylaminopropyl)-3-ethylcarbodi Imine) (5.35mmol, 830.94mg), 0.15 equivalents of DMAP (4-dimethylaminopyridine) (535.24mol, 65.39mg) were d...

Embodiment 1

[0072] Preparation of compound 1-1: There are two methods for the preparation of this compound. The first method is to obtain the product by one-step condensation with common condensing agents (DMAP, EDAC); the second method is to use p-aminobenzoic acid to form p- Aminobenzoyl chloride, the amino group generally does not participate in the reaction because the amino hydrochloride is formed, and then the reaction product is drained for use, and 2,4,6-trihydroxyacetophenone is dissolved in boron trifluoride ether, and the The target product can be obtained by adding the product dropwise into the reaction liquid. Due to the harsh experimental conditions required by the reaction and environmental pollution, the first method is used in this embodiment.

[0073] 1.2 equivalents of p-aminobenzoic acid (4.28mmol, 587.22mg), 1.5 equivalents of EDAC (1-(3-dimethylaminopropyl)-3-ethylcarbodiimide) (5.35mmol, 830.94mg), 0.15 equivalent of DMAP (4-dimethylaminopyridine) (535.24mol, 65.39m...

Embodiment 2

[0077] Preparation of compound 2-1: see the method of compound 1-1, the only difference is that the 2,4,6-trihydroxyacetophenone in Example 1 is replaced by 2,4-dihydroxybenzoic acid to obtain a white solid, the yield About 51%. 1 H NMR (DMSO-d 6 ,400MHz,25℃)δ10.69(s,1H),7.82(d,J=8.7,1H),7.79-7.76(m,2H),6.86-6.85(d,J=2.3,1H),6.81- 6.79(dd, J=8.7,2.3,1H),6.66-6.62(d,J=8.7,2H),6.22(s,1H),3.88(s,3H); 13 C NMR (DMSO-d 6 ,101MHz,25℃)δ168.8,163.9,161.2,156.5,154.6,132.2,131.2,113.9,113.8,112.9,110.7,110.5,52.5.

[0078] Preparation of compound 2-2: see the method of compound 1-2, the only difference is that the 2,4,6-trihydroxyacetophenone in Example 1 is replaced by 2,4-dihydroxybenzoic acid, white solid, the yield is about was 61%. 1 H NMR (DMSO-d 6 ,400MHz,25℃)δ10.68(s,1H),7.82(d,J=8.7Hz,1H),7.68(s,1H),7.66(d,J=2.1Hz,1H),6.85(d, J=2.2Hz, 1H), 6.80(dd, J=8.7, 2.3Hz, 1H), 6.66(dd, J=8.7, 2.3Hz, 1H), 5.98(br-s, 2H), 3.88(s, 3H ),2.10(s,3H); 13 C NMR (DMSO-d 6 101 MHz, 25°C...

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Abstract

The invention provides a phenol AB ring structure compound and a preparation method and application thereof, and belongs to the field of organic synthesis. An AB ring structure in the phenol AB ring structure compound provided by the invention has relatively good anti-influenza virus neuraminidase activity, and also has moderate-intensity inhibitory activity on daphenanthrene drug-resistant AnhuiN9 (H7N9). The preparation method provided by the invention is simple in process and easy to implement, the synthesis method is simpler than that of a positive drug daphenanthrene, the compound 1-1 can be completed in only one step, and the compound 3-5-10 needs to be synthesized in four steps.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a phenolic compound with an AB ring structure and a preparation method and application thereof. Background technique [0002] Polyphenolic compounds have great medicinal value in anti-influenza. 2,4,6-trihydroxyacetophenone and 2,4-dihydroxybenzoic acid methyl ester analogues belong to polyphenolic compounds. Polyphenols not only have potential antioxidant properties, protecting cells from oxidative damage, but have also made progress against influenza in recent years. For example, tea polyphenols are consistent with influenza neuraminidase and influenza-infected cells in vitro, and bitter tea extract has a good lung index inhibition rate for mice infected with H9N2 influenza virus strains; Gao Zengping’s research team will The isolated 12 polyphenolic compounds and the neuraminidase in influenza and the verification of the target compound by the cytopathic pathology ...

Claims

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Application Information

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IPC IPC(8): C07C229/60C07C229/64C07C233/54C07C205/57C07C237/32C07C237/44C07D277/06C07D277/36C07D277/40C07D277/56C07C243/20C07C243/18C07C241/02C07C201/12C07C227/18C07C231/12C07C231/02A61P31/16
CPCA61P31/16C07C205/57C07C229/60C07C229/64C07C233/54C07C237/32C07C237/44C07C243/18C07C243/20C07D277/06C07D277/36C07D277/40C07D277/56C07C2603/74
Inventor 周俊胡江苗侯博杨柳
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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