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Pleuromutilin derivative with 2-amino phenyl mercaptan side chain and preparing method and application of pleuromutilin derivative

A technology of pleuromutilin and aminophenylthiol, which is applied in thioether preparation, sulfonate preparation, organic chemistry, etc., can solve the problem of rare drug-resistant bacteria, and achieve the effect of good in vitro antibacterial activity

Inactive Publication Date: 2017-04-19
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]Since the mechanism of action of pleuromutilin compounds is different from that of antibiotics widely used in clinical practice, there are not many resistant bacteria to pleuromutilin antibiotics See

Method used

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  • Pleuromutilin derivative with 2-amino phenyl mercaptan side chain and preparing method and application of pleuromutilin derivative
  • Pleuromutilin derivative with 2-amino phenyl mercaptan side chain and preparing method and application of pleuromutilin derivative
  • Pleuromutilin derivative with 2-amino phenyl mercaptan side chain and preparing method and application of pleuromutilin derivative

Examples

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Effect test

Embodiment 1

[0061] Example 1: Synthesis of 22-O-[2-(2-methylbenzamide)phenyl]thioacetyl Murelin (Compound 1)

[0062] Intermediate II 0.82g (1.88mmol) was dissolved in 35ml ethyl acetate, 2-methylbenzoic acid (2.07mmol) and oxalyl chloride 2.07mmol were added, heated and stirred at about 70°C for 1 hour to obtain the target product. The resulting mixed solution was evaporated to dryness by rotating to make the mixture redissolved in dichloromethane. Add 1g of 100-200 mesh silica gel and mix thoroughly. After the solvent evaporates, the above crude product-silica powder mixture is purified by column chromatography (200~300 The mesh silica gel powder is the stationary phase, and petroleum ether: ethyl acetate=1:1 is the mobile phase) to obtain the product 22-O-[2-(2-methylbenzamide)phenyl]thioacetyl murine ( The pure product of compound 1). The yield was 86.55%. HR-MS(ESI): Cal: 604.3091; Found: 604.3117.

Embodiment 2

[0063] Example 2: Synthesis of 22-O-[2-(3-methylbenzamido)phenyl]thioacetylmurine (Compound 2)

[0064] Intermediate II 0.82g (1.88mmol) was dissolved in 35ml of dichloromethane, 3-methylbenzoic acid (2.07mmol) and tert-butyl chloroformate 2.07mmol were added, heated and stirred at about 70°C for 1 hour to obtain the target product. The resulting mixed solution was evaporated to dryness by rotating to make the mixture redissolved in dichloromethane. Add 1g of 100-200 mesh silica gel and mix thoroughly. After the solvent evaporates, the above crude product-silica powder mixture is purified by column chromatography (200~300 The mesh silica gel powder is the stationary phase, and petroleum ether: ethyl acetate=1:1 is the mobile phase) to obtain the product 22-O-[2-(3-methylbenzamide)phenyl]thioacetyl Murelin ( Compound 2) pure product. The yield was 85.75%. HR-MS(ESI): Cal: 604.3091; Found: 604.3110.

Embodiment 3

[0065] Example 3: Synthesis of 22-O-[2-(4-methylbenzamido)phenyl]thioacetylmurine (Compound 3)

[0066] 0.82g (1.88mmol) of Intermediate II was dissolved in 35ml of dichloromethane, 4-methylbenzoic acid (2.07mmol) and 2.07mmol of thionyl chloride were added, heated and stirred at about 70°C for 1 hour to obtain the target product. The resulting mixed solution was evaporated to dryness by rotating to make the mixture redissolved in dichloromethane. Add 1g of 100-200 mesh silica gel and mix thoroughly. After the solvent evaporates, the above crude product-silica powder mixture is purified by column chromatography (200~300 The mesh silica gel powder is the stationary phase, and petroleum ether: ethyl acetate=1:1 is the mobile phase) to obtain the product 22-O-[2-(4-methylbenzamide)ethyl]thioacetyl murine ( Compound 3) pure product. The yield was 83.09%. HR-MS(ESI): Cal: 604.3091; Found: 604.3110.

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Abstract

The invention belongs to the field of medicinal chemistry and discloses a pleuromutilin derivative with a 2-amino phenyl mercaptan side chain and a preparing method and application of the pleuromutilin derivative. The compound has the structures shown in formula 2 and formula 3, wherein R1, R2 and R3 are respectively and independently selected from the hydrogen atom, the hydroxyl, the amino, the sulfydryl, the hydroxymethyl, the amine methyl, the nitro, the halogen, the trihalogenated methyl, the methyl, the natural amino acid acylamino and the C1-6 alkoxy. The pleuromutilin derivative with the 2-amino phenyl mercaptan side chain has good activity for inhibiting the drug resistant staphylococcus aureus and the mycoplasma and is particularly suitable for serving as a novel antibacterial medicine for preventing infectious diseases caused by the human or animal mycoplasma or drug resistant staphylococcus aureus or multidrug resistant bacteria.

Description

Technical field [0001] The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with 2-aminobenzene mercapto alcohol side chain, and a preparation method and application thereof. Background technique [0002] Methicillin-resistant Staphylococcus aureus (MRSA) is a pathogen with a wide range of epidemics, strong pathogenicity, and high morbidity and mortality. Once the human body is infected, it can cause fever, poor spirits, and local infection symptoms. The most common is lung infection. Others such as skin, urinary tract, maternal reproductive tract infections, severe cases of sepsis, prolong the patient’s hospital stay, if treatment is not timely, Can endanger the life of the patient. An investigation in the Netherlands in 2003 showed that about 39% of slaughtered pigs contained ST398 MRSA and 27% of breeders carried MRSA from pigs. MRSA ST398 of animal origin can cause human infections in contact with animals. MRSA i...

Claims

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Application Information

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IPC IPC(8): C07C319/14C07C319/20C07C323/52C07C303/28C07C309/73A61K31/22A61P31/04
CPCC07C319/14C07C303/28C07C309/73C07C319/20C07C323/52
Inventor 汤有志张昭圣刘雅红
Owner SOUTH CHINA AGRI UNIV
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