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Curcumenol derivatives resisting influenza A(H1N1) virus

A technology of influenza virus and curcumol, applied in the field of medicine, can solve problems such as poor water solubility, achieve stable quality, high drug purity, and good research and development prospects

Active Publication Date: 2015-03-25
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor water solubility, it is only easily soluble in small polar organic solvents such as ethanol, acetone, and chloroform, and has not been developed into clinical medicine for a long time.
In view of the limitation of chemically variable sites in its structure, so far there are few reports on its structural modification by organic chemical methods

Method used

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  • Curcumenol derivatives resisting influenza A(H1N1) virus
  • Curcumenol derivatives resisting influenza A(H1N1) virus
  • Curcumenol derivatives resisting influenza A(H1N1) virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of compound of the present invention (1)

[0042] Preparation of intermediates:

[0043] Dissolve m-CPBA (17.2g, 1mol) in dichloromethane (100ml), add curcumol (11.8g, 0.05mol) in dichloromethane (100ml) solution at 0°C, keep stirring at 0°C for 2 hours . After the reaction, the reaction liquid was extracted three times with NaOH (2 mol / l) solution, the organic phases were combined, extracted with water until neutral, and dried over anhydrous sodium sulfate. The solution was concentrated and evaporated to dryness, and the crude product was purified by silica gel column chromatography (cyclohexane:ethyl acetate=50:1~10:1) to obtain 11.95 g of white waxy solid 10,14-epoxycurcumol, yield 95% .

[0044]10,14-epoxycurcumol (10.08g, 0.04mol) was dissolved in acetonitrile (600ml), and lithium perchlorate trihydrate (6.4g, 0.04mol) and diethylamine (20ml) were added at room temperature. The resulting mixture was heated to reflux overnight. The...

Embodiment 2

[0048] Embodiment 2: the preparation of compound of the present invention (2)

[0049] Preparation of intermediate: same as the preparation method of intermediate in Example 1.

[0050] Preparation of target compound (2):

[0051] Dissolve (1S,4S,5S,7S,8R)-5,8-epoxy-9,10-ene-14-chloroguaiacol (27mg, 0.1mmol) in DMF (2ml) and add acetic acid Sodium (12.3 mg, 0.15 mmol). The resulting mixture was reacted at 70°C for 3.5 hours. The reaction solution was concentrated and evaporated to dryness, and the resulting crude product was purified by PTLC (cyclohexane:ethyl acetate=3:1, ethyl acetate eluted) to obtain colorless oily compound (1S,4S,5S,7S,8R)-5,8 - Epoxy-9,10-ene-8-hydroxy-14-guaiacol acetate (2) 21.2 mg, yield 72%. The spectral data of the compound are as follows: MS(ESI)m / z:317.0[M+Na] + ; 1 H-NMR (300MHz, CDCl 3 )δ(ppm): 1.96(1H,dd,J=8.8,16.4Hz,H-1), 1.87(1H,m,H-2a), 1.56(1H,m,H-2b), 1.87(1H, m, H-3a), 1.56(1H, m, H-3b), 1.80(1H, m, H-4), 2.19(1H, dd, J=10.7, 12.6...

Embodiment 3

[0052] Embodiment 3: the preparation of compound (3) of the present invention

[0053] Preparation of intermediate: same as the preparation method of intermediate (1S, 4S, 5S, 7S, 8R)-5,8-epoxy-9,10-ene-8,14-guaiacol in Example 1.

[0054] Preparation of target compound (3):

[0055] Dissolve (1S,4S,5S,7S,8R)-5,8-epoxy-9,10-ene-8,14-guaiarediol (25.2mg, 0.1mmol) in dry pyridine (4ml) , succinic anhydride (15mg, 0.15mmol), DMAP (2.5mg, 0.02mmol) were added. The resulting mixture was reacted at 70°C for 2 hours. The reaction solution was concentrated and evaporated to dryness, and the resulting crude product was purified by PTLC (cyclohexane:ethyl acetate=2:1, eluted with ethyl acetate) to obtain colorless oily compound (1S,4S,5S,7S,8R)-5,8 - Epoxy-9,10-ene-8-hydroxy-14-guaiacol succinate (3) 24.6 mg, yield 71%. The spectral data of the compound are as follows: MS(ESI)m / z:361.2[M+Na] + ; 1 H-NMR (300MHz, CDCl 3 )δ(ppm): 1.95(1H,dd,J=8.8,16.3Hz,H-1), 1.86(1H,m,H-2a), 1.52(...

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Abstract

The invention belongs to the technical field of medical technology, and relates to novel compounds, which are shown in a general formula (I) and have the activity of resisting influenza A(H1N1) virus, wherein R1 and R2 are defined as in the specification. The invention also relates to application and a preparation method of the compounds, and clinically acceptable medicines for treating infectious diseases of influenza A(H1N1) virus, which are prepared by combining the compounds with pharmaceutically acceptable carriers. The structure of formula (I) is shown in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a curcumol derivative against influenza A (H1N1) virus. Background technique [0002] Influenza (influenza) is a highly contagious, fast-spreading acute viral respiratory infectious disease that seriously endangers the health of people, livestock and poultry caused by influenza virus, and is a typical zoonotic disease. It is generally accepted by the medical profession that the harm of influenza is no less than that of AIDS and war. Complications and death from influenza can be severe. According to the announcement issued by the World Health Organization (WHO), there are 600 million to 1.2 billion cases of influenza in the world every year, and 500,000 to 1 million deaths, including 3 million to 5 million cases of severe influenza, and the fatality rate of severe influenza is 8%. -10%. Influenza not only causes morbidity and death of a large number of people, but also causes ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08A61K31/35A61P31/16
Inventor 邱峰李天宪王绍杰陈丽霞康宁罗桓
Owner SHENYANG PHARMA UNIVERSITY
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