Unlock instant, AI-driven research and patent intelligence for your innovation.

Chiral gossypol acid with activity on resistance to avian influenza virus and preparation method for same

A technology of avian influenza virus and gossypol acid, applied in the field of chiral gossypol acid and its preparation, can solve the problems of Tamiflu resistance, slow development of anti-avian influenza virus drugs, few varieties, etc., and achieve strong inhibitory effect Effect

Inactive Publication Date: 2012-06-27
WUHAN UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although bird flu has a great impact, the development of anti-bird flu drugs is slow and there are few varieties
Type A avian influenza virus has developed resistance to amantadine. Imported Tamiflu is currently the only effective drug for treating avian influenza at home and abroad, but there have been reports of Tamiflu resistance in foreign countries
There is no report on chiral gossypol acid against avian influenza virus

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Chiral gossypol acid with activity on resistance to avian influenza virus and preparation method for same
  • Chiral gossypol acid with activity on resistance to avian influenza virus and preparation method for same
  • Chiral gossypol acid with activity on resistance to avian influenza virus and preparation method for same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] L-gossypol acid ( I ), the specific steps are as follows:

[0042] 1. Preparation of L-gossypol ((-)-gossypol) (see publication number CN 101020626A, date of publication is August 22, 2007, invention name is high-purity optically active (-)-gossypol or (+ )-Chinese patent of the preparation method of gossypol), as follows:

[0043] 1.1 Preparation of (-)-gossypol-L-tryptophan methyl ester Schiff base and (+)-gossypol-L-tryptophan methyl ester Schiff base

[0044] (a) Preparation of (-)-gossypol-L-tryptophan methyl ester Schiff base:

[0045] Weigh 15.736g (61.776×10 -3 mol) L-tryptophan methyl ester hydrochloride was dissolved in 200ml ethanol, and 2.471g (61.776×10 -3 mol) NaOH, after dissolved, add 16.017g (30.888×10 -3 mol) gossypol, reacted at 45°C for 4h. After the reaction was complete, the system was turbid, and a yellow solid precipitated out. Suction filtration, the yellow solid was washed with ethanol and dried to obtain 6.453 g of (-)-gossypol-L-tryptop...

Embodiment 2

[0058] The preparation of D-gossypol acid, concrete steps are as follows:

[0059] 1. Preparation of dextro-gossypol ((+)-gossypol) (see publication number CN 101020626A, date of publication is August 22, 2007, invention name is high-purity optically active (-)-gossypol or ( +)-Chinese patent of the preparation method of gossypol), as follows:

[0060] Weigh 3.00g (3.268×10 -3 mol)(+)-gossypol-L-tryptophan methyl ester Schiff base (see step 1.1(b) in Example 1 for its preparation) was dissolved in 200ml of ether, added 12ml of glacial acetic acid, at 50°C Stir. Add 100 μL of concentrated hydrochloric acid (hydrochloric acid concentration is 37%), stir for 2 hours, after the reaction is over, filter to remove the insoluble white powder, wash the ether layer with water until pH ≈ 7, dry it with anhydrous sodium sulfate, concentrate the ether solution, add petroleum ether to crystallize Precipitate, dry to obtain 1.16g yellow powder D-gossypol ((+)-gossypol), yield 68.5%. [α]...

Embodiment 3

[0070] Anti-avian influenza virus experiment of L-gossyphenolic acid and D-gossyphenolic acid

[0071] 1. Experimental materials

[0072] (1) Virus: H 5 N1 The virus strain is A / VietNam / 1194 / 2004, and its titer was 4×10 9 PFU / ml, press 10 with culture medium at the time of infection -2 The dilution, namely 40~50PFU / well, was provided by the State Key Laboratory of Virology, Wuhan University.

[0073] (2) Cells: MDCK cells (sourced from China Center for Type Culture Collection, MDCK cells are classic cells for influenza virus plaque experiments), provided by the State Key Laboratory of Virology, Wuhan University.

[0074] (3) Positive control drug: amantadine, provided by the State Key Laboratory of Virology, Wuhan University.

[0075] (4) Sample treatment: Amantadine and the compound of the present invention were prepared into a 10 mg / ml mother solution with DMSO, and diluted with DMSO to form a corresponding gradient when used.

[0076] 2. Experimental method

[0077] 2...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses chiral gossypol acid with an activity on resistance to avian influenza virus and a preparation method for the same. The chiral gossypol acid disclosed by the invention comprises levorotatory gossypol acid and dextrorotatory gossypol acid, wherein the structural formulas of the levorotatory gossypol acid and the dextrorotatory gossypol acid respectively are as follows: FORMULA and FORMULA. The preparation method comprises the following steps of: using levorotatory gossypol or dextrorotatory gossypol as a raw material; performing acetylation protection on the phenolic hydroxyl of the levorotatory gossypol or the dextrorotatory gossypol; oxidizing the aldehyde group thereof; and finally performing deacetylation to obtain the levorotatory gossypol acid and the dextrorotatory gossypol acid. The chiral gossypol acid disclosed by the invention has a very strong inhibitory activity on H5N1 avian influenza virus A / VietNam / 1194 / 2004.

Description

[0001] technical field [0002] The invention belongs to the field of organic medicinal chemistry, and in particular relates to chiral gossypol acid with anti-avian influenza virus activity and a preparation method thereof. Background technique [0003] Influenza is an acute respiratory infectious disease caused by influenza virus. The first human case of H infection was reported in Hong Kong, China in 1997. 5 N 1 Since the fatal case of bird flu of type A virus, the virus has been prevalent in China, Vietnam, Thailand and the Netherlands, and has the characteristics of high pathogenicity and high mortality. The current type A bird flu virus circulating in my country is H 5 N 1 Subtype. Today, the whole world is facing the danger of avian influenza pandemic, especially the antigenic variation of avian influenza virus, or its genetic reassortment with the current A-type avian influenza virus circulating in the population to form a reassortment strain, resulting in Human ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/11C07C51/347A61K31/194A61P31/16
Inventor 杨健吴叔文田波陈刚
Owner WUHAN UNIV