Chemically modified fusidic acid, preparation method thereof and application of chemically modified fusidic acid

The technology of geoacid chemistry and fusidic acid is applied in the field of chemical modification of fusidic acid and its preparation, which can solve the problems of antibiotic drug abuse, influence human health and safety, etc., and achieves high synthesis yield, simple preparation method and application. wide range of effects

Active Publication Date: 2018-04-24
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are many types of antibacterial antibiotics in the domestic and foreign markets, but at the same time, due to the abuse of antibiotics, many drug-resistant su

Method used

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  • Chemically modified fusidic acid, preparation method thereof and application of chemically modified fusidic acid
  • Chemically modified fusidic acid, preparation method thereof and application of chemically modified fusidic acid
  • Chemically modified fusidic acid, preparation method thereof and application of chemically modified fusidic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] The preparation of embodiment 1 fusidic acid chemical modification (FA-E-01)

[0056] First weigh 300mg (0.581mmol) of fusidic acid and 142mg (1.161mmol) of 4-dimethylaminopyridine (DMAP) in a 50mL round-bottomed flask containing magnets, and measure 10mL under the condition of nitrogen protection Put ultra-dry anhydrous dichloromethane in a flask, and stir for about 15 minutes at room temperature and under nitrogen. After it is completely dissolved, add 0.94 mL (1.161 mmol) of pyridine with a syringe, and stir for about After 20 min, 0.20 mL (1.743 mmol) of three times the amount of benzoyl chloride was finally added, and the reaction was stirred for 2 h at room temperature under nitrogen protection. The end point of the reaction was detected by TLC (developing agent: dichloromethane: ethyl acetate = 3: 1, chromogen: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio) = 85: 10: 5: 0.5), the reaction was completed , the crude product of compo...

Embodiment 2

[0057] Preparation of Example 2 Fusidic Acid Chemical Modifications (FA-E-02)

[0058] First weigh 300mg (0.581mmol) of fusidic acid and 142mg (1.161mmol) of 4-dimethylaminopyridine (DMAP) in a 50mL round-bottomed flask containing magnets, and measure 10mL under the condition of nitrogen protection Put ultra-dry anhydrous dichloromethane in a flask, stir for about 15 min at room temperature and nitrogen protection, and then add 0.94 mL (1.161 mmol) of pyridine with a syringe, and stir at room temperature and nitrogen After about 20 minutes, three times the amount of p-toluoyl chloride 0.23 mL (1.743 mmol) was finally added, and the reaction was stirred for 2 hours at room temperature under nitrogen protection. The end point of the reaction was detected by TLC (developing agent: dichloromethane: ethyl acetate = 3: 1, chromogen: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio) = 85: 10: 5: 0.5), the reaction was completed , the crude product of com...

Embodiment 3

[0059] Preparation of Example 3 Fusidic Acid Chemical Modifications (FA-E-03)

[0060] First weigh 300mg (0.581mmol) of fusidic acid and 142mg (1.161mmol) of 4-dimethylaminopyridine (DMAP) in a 50mL round-bottomed flask containing magnets, and measure 10mL under the condition of nitrogen protection Put ultra-dry anhydrous dichloromethane in a flask, stir for about 15 min at room temperature and nitrogen protection, and then add 0.94 mL (1.161 mmol) of pyridine with a syringe, and stir at room temperature and nitrogen After about 20 minutes, three times the amount of m-toluoyl chloride 0.23 mL (1.743 mmol) was finally added, and the reaction was stirred for 2 hours at room temperature under nitrogen protection. The end point of the reaction was detected by TLC (developing agent: dichloromethane: ethyl acetate = 3: 1, chromogen: methanol: acetic acid: concentrated sulfuric acid: anisaldehyde (volume ratio) = 85: 10: 5: 0.5), the reaction was completed , the crude product of com...

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Abstract

The invention belongs to the technical field of medicinal chemical small molecule structure modified medicines, and discloses chemically modified fusidic acid, a preparation method thereof and an application of the chemically modified fusidic acid. The chemical structural formula of the chemically modified fusidic acid is as shown in the specification, and R is mono-substituted or poly-substitutedaromatic ring groups containing benzene rings and/or thiophene rings or furan rings. Fusidic acid serving as an extract of a natural product is structurally chemically modified to obtain the aromaticring group substituted chemically modified fusidic acid. The chemically modified fusidic acid can be applied to preparation of a medicinal preparation and antibacterial activity of bacteria, and is also applied to preparation of bacterial infection prevention, inhibition, control and/or treatment. In addition, the chemically modified fusidic acid can also be applied to the field of food or drinksafety and/or instrument disinfection.

Description

technical field [0001] The invention belongs to the field of medicinal chemical small molecule structure modification, and more specifically relates to a chemical modification of fusidic acid and its preparation method and application. Background technique [0002] Fusidic acid cream or sodium fusidic acid prepared from fusidic acid is a natural antibacterial drug widely used in the market. The chemical structural formula of fusidic acid is shown in formula 2: [0003] [0004] The main common dosage forms of fusidic acid are antibacterial cream, tablet, eye drops and injection. Fusidic acid is an antibiotic with a steroidal skeleton structure. It was first extracted from fungi by the Danish Leo Pharmaceutical Company in 1962. Its chemical structure is similar to that of sporin P. It mainly inhibits the synthesis of bacterial proteins. antibacterial effect. Fusidic acid has a strong antibacterial effect on a series of Gram-positive bacteria, especially on strains of Sta...

Claims

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Application Information

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IPC IPC(8): C07J13/00C07J17/00C07J33/00A61K31/56A61K31/58A61P31/04A01N45/00A01N43/08A01N43/10A01N43/12A01P1/00
CPCA01N43/08A01N43/10A01N43/12A01N45/00C07J13/00C07J17/00C07J33/002
Inventor 赵肃清张炳杰吴盼盼钟颖颖梁汉英张春国江政云方颖林高美婷杨洋朱秋雁
Owner GUANGDONG UNIV OF TECH
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