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Benzodihydropyran compound with anti-hepatitis B virus and anti-coronavirus effect

A technology of chroman and dihydropyran, which is applied in antiviral agents, organic chemistry, medical preparations containing active ingredients, etc., to achieve the effect of easy raw materials, good inhibitory effect, and mild reaction conditions

Active Publication Date: 2022-08-09
YUNNAN MINZU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are limited antiviral drugs available to fight against SARS-CoV-2 infection. Under the background of the current COVID-19 global pandemic and the continuous mutation of SARS-CoV-2, effective and safe antiviral drugs have been developed and widely promoted. It is an important measure to reduce the risk of disease

Method used

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  • Benzodihydropyran compound with anti-hepatitis B virus and anti-coronavirus effect
  • Benzodihydropyran compound with anti-hepatitis B virus and anti-coronavirus effect
  • Benzodihydropyran compound with anti-hepatitis B virus and anti-coronavirus effect

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preparation example Construction

[0044] The preparation method of the compound shown in the formula I of the present invention includes but is not limited to the preparation method of the compound shown in the formula II and the compound shown in the formula III. The preparation method of the compound shown in the formula II: the compound shown in the formula IV is The raw material is reacted with copper bromide using ethyl acetate as a solvent under reflux conditions to obtain the brominated product shown in formula V. Then, the brominated product shown in formula V and triphenylphosphorus were dissolved in ethyl acetate, and reacted at room temperature to obtain a white solid; sodium hydroxide solution (2N) was added to the dichloromethane solution in which the white solid was dissolved, and adjusted pH to 12. After stirring at room temperature for 30 min, the compound represented by formula VI can be obtained. The compound represented by the formula VI and the aldehyde are dissolved in dichloromethane, an...

Embodiment 1

[0072] Example 1: Preparation of Intermediate I-1

[0073]

[0074] 2,4-Dihydroxyacetophenone (15.21 g, 0.1 mol) was dissolved in 1 L of acetone and potassium carbonate (55.2 g, 0.4 mol) was added. Dimethyl sulfate (0.11 mol) was added in an ice bath, the dropwise addition was completed, the temperature was returned to room temperature, and the mixture was heated to reflux in an oil bath for 5 hours. After the reaction was completed, 500 mL of ice water was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined and washed three times with saturated NaCl, then dried over anhydrous magnesium sulfate. After being concentrated by distillation under reduced pressure, intermediate I-1 was obtained after purification by silica gel chromatography with a yield of 90%.

[0075] 1 H-NMR (400MHz, CDCl 3 ),δ12.75(s,1H),7.63(d,J=8.7Hz,1H), 6.44(dd,J=8.7,2.5Hz,1H),6.42(d,J=2.4Hz,1H),3.84 (s,3H),2.56 (s,3H). 13 C-NMR (100MHz, CDCl 3)δ20...

Embodiment 2

[0076] Example 2: Preparation of Intermediate I-2

[0077]

[0078] Intermediate I-1 (16.62 g, 0.1 mol) was dissolved in ethyl acetate (1500 mL), copper bromide was added at room temperature, and heated under reflux for 12 h. After cooling to room temperature, the mixture was filtered and neutralized with saturated aqueous sodium bicarbonate solution. After three extractions with ethyl acetate, the organic phases were combined, washed three times with saturated NaCl, dried over anhydrous magnesium sulfate, and concentrated by distillation under reduced pressure to obtain the crude product. Then after purification by silica gel chromatography and recrystallization, intermediate I-2 was obtained in 90% yield.

[0079] 1 H NMR (400MHz, CDCl 3 )δ12.22(s, 1H), 7.65(d, J=8.9Hz, 1H), 6.48(dd, J=8.9, 2.5Hz, 1H), 6.45(d, J=2.5Hz, 1H), 4.36( s,2H),3.86(s,3H). 13 C-NMR (100MHz, CDCl 3 )δ195.3, 167.1, 166.4, 132.1, 111.3, 108.5, 101.3, 55.8, 29.8.

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Abstract

The invention relates to a benzodihydropyran compound with effects of resisting hepatitis B virus and coronavirus, especially SARS-CoV-2, and a preparation method and application of the benzodihydropyran compound. Specifically, the invention provides a preparation method and application of a compound as shown in a formula I. The compound is used for preventing, treating or relieving hepatitis B virus infectious diseases and coronavirus infectious diseases. The compound disclosed by the invention has relatively strong activity of resisting hepatitis B virus and coronavirus, especially SARS-CoV-2, and is used as an active component to be prepared into a medicine or a medicine composition for resisting hepatitis B virus or coronavirus together with a pharmaceutically acceptable carrier or auxiliary materials.

Description

technical field [0001] The present invention relates to chroman compounds with anti-hepatitis B virus and coronavirus, in particular to the use of chroman compounds in the preparation of anti-hepatitis B virus or anti-SARS-CoV-2 medicines. Background technique [0002] Viruses are non-cellular organisms that are small in size and simple in structure, take DNA or RNA as genetic material, and must parasitize in living cells and multiply by replication (Woolhouse M, Scott F, Hudson Z, et al.Humanviruses:discovery and emergence[J]. Philos Trans R Soc Lond B Biol Sci, 2012, 367:2864-2871). Virus infection can be divided into acute viral infection caused by influenza virus, new coronavirus pneumonia virus (SARS-CoV-2), and acute viral infection caused by human immunodeficiency virus (HIV) and hepatitis B virus (HBV) according to the time the virus stays in the body. persistent viral infection. The life cycle of a virus can be roughly divided into stages such as invasion, biosynt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/74A61K31/353A61P31/20A61P31/14
CPCC07D311/74A61P31/20A61P31/14Y02P20/55
Inventor 黄相中白溪山李育晓李艳红
Owner YUNNAN MINZU UNIV
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