Dextro-gossypol amino acid sodium salt derivative for blocking invasion of H5N1 avian influenza virus, and preparation method and application thereof

A technology of d-gossypol amino acid and avian influenza virus, which is applied in the field of organic medicinal chemistry, can solve problems such as unsatisfactory selectivity index, and achieve the effects of practical value, low toxicity, and strong anti-H5N1 avian influenza virus activity

Inactive Publication Date: 2012-11-14
WUHAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Through further research, the inventors found that gossypol with different optical activities had certain differences in anti-H5N1 avian influenza virus activity, and d-gossypol was anti-H5N1. 5 N 1 Avian influenza virus activity is stronger than L-gossypol, D-gossypol (half inhibitory concentration IC 50 =0.97μg / ml, half toxic concentration CC 50 =1.83μg / ml) anti-H 5 N 1 The activity of avian influenza virus is about that of L-gossypol (half inhibitory concentration IC 50 =1.74μg / ml, half toxic concentration CC 50 =18.32μg / ml), twice as much as the positive control drug amantadine, but the cytotoxicity of D-gossypol is almost 10 times that of L-gossypol, and the selectivity index is not ideal
At present, there is no anti-H 5 N 1 Research Report on Avian Influenza Virus

Method used

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  • Dextro-gossypol amino acid sodium salt derivative for blocking invasion of H5N1 avian influenza virus, and preparation method and application thereof
  • Dextro-gossypol amino acid sodium salt derivative for blocking invasion of H5N1 avian influenza virus, and preparation method and application thereof
  • Dextro-gossypol amino acid sodium salt derivative for blocking invasion of H5N1 avian influenza virus, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of (+)-gossypol-L-alanine sodium Schiffer base, concrete steps are as follows:

[0037] 100mg (1.930×10 -4mol)(+)-gossypol (also known as D-gossypol) was dissolved in 10mL of absolute ethanol to obtain an organic solution of D-gossypol; 34.4mg (3.861×10 -4 mol) L-alanine and 15.4mg (3.861×10 -4 mol) sodium hydroxide was mixed and dissolved in 10 mL of absolute ethanol, and stirred at room temperature for 30 minutes to obtain an ethanol solution of sodium L-alanine. Add the organic solution of gossypol to the ethanol solution of L-sodium alanine to obtain the reaction solution, under the protection of nitrogen, use the methanol solution of sodium hydroxide to control the pH of the reaction solution = 7.0 ~ 7.5, the reaction solution in Reflux and stir at 80°C for 4 hours. After evaporating the solvent, the solid obtained was recrystallized from acetone, filtered and vacuum-dried successively to obtain (+)-gossypol-L-alanine sodium Schiffer base, yield: ...

Embodiment 2

[0039] The preparation of (+)-gossypol-L-tryptophan sodium Schiffer base, concrete steps are as follows:

[0040] 100mg (1.930×10 -4 mol)(+)-gossypol (also called d-gossypol) was dissolved in 10mL absolute ethanol to obtain an organic solution of d-gossypol; 78.8mg (3.861×10 -4 mol) L-tryptophan with 15.4mg (3.861×10 -4 mol) sodium hydroxide was mixed and dissolved in 10 mL of absolute ethanol, and stirred at room temperature for 30 minutes to obtain an ethanol solution of L-tryptophan sodium. Add the organic solution of gossypol to the ethanol solution of sodium L-chromoaminoacid to obtain the reaction solution, under the protection of nitrogen, use the methanol solution of sodium hydroxide to control the pH of the reaction solution = 7.0 ~ 7.5, the reaction solution at 80 Stir at reflux for 4 hours, distill off the solvent and recrystallize the obtained solid from acetone, filter and vacuum-dry successively to obtain (+)-gossypol-L-tryptophan sodium Schiffer base, yield: 7...

Embodiment 3

[0042] (+)-gossypol-sodium taurine Schiffer base, the specific steps are as follows:

[0043] 100mg (1.930×10 -4 mol)(+)-gossypol (also known as D-gossypol) was dissolved in 10mL of absolute ethanol to obtain an organic solution of D-gossypol; 42.1mg (3.861×10 -4 mol) taurine and 15.4mg (3.861×10 -4 mol) sodium hydroxide was mixed and dissolved in 10 mL of absolute ethanol, and stirred at room temperature for 30 minutes to obtain an ethanol solution of sodium taurine. Add the organic solution of gossypol to the ethanol solution of sodium taurate to obtain the reaction solution, under the protection of nitrogen, use the methanol solution of sodium hydroxide to control the pH of the reaction solution = 7.0 ~ 7.5, and put the reaction solution at 80 ° C Reflux and stir for 4 hours, evaporate the solvent and recrystallize the obtained solid with acetone, filter and vacuum-dry successively to obtain (+)-gossypol-sodium taurine Schiffer base, yield: 87.9%.[α] 20 D :+60°(c0.04,CH...

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Abstract

The invention discloses a dextro-gossypol amino acid sodium salt derivative for blocking the invasion of an H5N1 avian influenza virus, and a preparation method and application thereof. The preparation method comprises the following steps: dissolving dextro-gossypol in an organic solvent to prepare a dextro-gossypol organic solution; dissolving amino acid and NaOH in an organic solvent to obtain an amino acid sodium organic solvent; mixing the dextro-gossypol organic solution and the amino acid sodium organic solvent to obtain a reaction liquid, and controlling the pH value of the reaction liquid to be 7.0-7.5; and enabling the reaction liquid to react in reflux conditions under the protection of nitrogen, then distilling out the organic solvent, and recrystallizing the obtained solids with acetone to obtain the dextro-gossypol amino acid sodium salt derivative. The dextro-gossypol amino acid sodium salt derivative has high activity of inhibiting the H5N1 avian influenza virus, and the activity of the derivative is higher than that of amantadine; and the dextro-gossypol amino acid sodium salt derivative acts on the entry phase of H5N1 virus infected cells. Thus, the dextro-gossypol amino acid sodium salt derivative can be used as an effective constituent in medicaments for preventing or treating H5N1 avian influenza.

Description

technical field [0001] The invention belongs to the field of organic medicinal chemistry, and in particular relates to a method for blocking H 5 N 1 The invention relates to a sodium salt derivative of d-gossypol amino acid invaded by avian influenza virus, and also relates to a preparation method and application of the sodium salt derivative of d-gossypol amino acid. Background technique [0002] Avian influenza is a highly pathogenic and high-mortality infectious disease common to humans and birds. Now, the whole world is facing the danger of avian influenza pandemic, especially the antigenic variation of avian influenza virus, or its The gene reassortment of type A avian influenza virus prevalent in the population at present forms a reassortant strain, which causes human influenza outbreaks. [0003] Although avian influenza has a great impact, the development of anti-avian influenza virus drugs is slow and there are few varieties. Type A avian influenza virus has deve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/16C07C227/18C07D209/20C07C309/14C07C303/32C07C229/36A61P31/16
Inventor 杨健吴叔文李龙龙潘薇张芳李菊蓉
Owner WUHAN UNIV
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