A pleuromutilin derivative with 2-aminoethanethiol side chain and its preparation method and application

A technology of pleuromutilin and aminomethanol, which is applied in the preparation of organic compounds, medical preparations containing active ingredients, preparation of sulfides, etc., can solve the problem of rare pleuromutilin-resistant bacteria and other issues to achieve good antibacterial activity in vitro

Active Publication Date: 2019-09-03
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Due to the unique antibacterial mechanism of pleuromutilin antibiotics, and this type of drug will not produce cross-resistance with other drugs, drug-resistant bacteria against pleuromutilin antibiotics are still rare

Method used

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  • A pleuromutilin derivative with 2-aminoethanethiol side chain and its preparation method and application
  • A pleuromutilin derivative with 2-aminoethanethiol side chain and its preparation method and application
  • A pleuromutilin derivative with 2-aminoethanethiol side chain and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: 22-O-[2-(2-methylbenzamido) ethyl] thioacetyl muulin (compound 1) synthesis

[0057] Intermediate II 0.82g (1.88mmol) was dissolved in 35ml of ethyl acetate, 2-methylbenzoic acid (2.07mmol) and oxalyl chloride 2.07mmol were added, heated and stirred at 70°C for 1 hour to obtain the target product. The obtained mixed solution was rotary evaporated to dryness, and the mixture was redissolved in dichloromethane, and 1 g of 100-200 mesh silica gel was added to mix thoroughly. After the solvent evaporated, the above crude product-silica gel powder mixture was purified by column chromatography (200-300 Mesh silica gel powder is stationary phase, sherwood oil: ethyl acetate=1:1 is mobile phase), obtains product 22-O-[2-(2-methylbenzamido) ethyl] thioacetylmyulin ( Pure product of compound 1). Yield 86.21%. HR-MS (ESI): CalforC 32 h 45 NO 5 S(M-H+): 556.3091; Found: 556.3110.

Embodiment 2

[0058] Example 2: Synthesis of 22-O-[2-(3-methylbenzamido) ethyl] thioacetyl muulin (compound 2)

[0059] 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 70°C for 1 hour to obtain the target product. The obtained mixed solution was rotary evaporated to dryness, and the mixture was redissolved in dichloromethane, and 1 g of 100-200 mesh silica gel was added to mix thoroughly. After the solvent evaporated, the above crude product-silica gel powder mixture was purified by column chromatography (200-300 Mesh silica gel powder is stationary phase, petroleum ether: ethyl acetate=1:1 is mobile phase), obtains product 22-O-[2-(3-methylbenzamido) ethyl] thioacetylmyulin ( The pure product of compound 2). Yield 83.45%. HR-MS (ESI): CalforC 32 h 45 NO 5 S(M-H+): 556.3091; Found: 556.3107.

Embodiment 3

[0060] Example 3: Synthesis of 22-O-[2-(4-methylbenzamido) ethyl] thioacetyl muulin (compound 3)

[0061] Intermediate II 0.82g (1.88mmol) was dissolved in 35ml of dichloromethane, 4-methylbenzoic acid (2.07mmol) and thionyl chloride 2.07mmol were added, heated and stirred at 70°C for 1 hour to obtain the target product. The obtained mixed solution was rotary evaporated to dryness, and the mixture was redissolved in dichloromethane, and 1 g of 100-200 mesh silica gel was added to mix thoroughly. After the solvent evaporated, the above crude product-silica gel powder mixture was purified by column chromatography (200-300 Mesh silica gel powder is stationary phase, and petroleum ether: ethyl acetate=1:1 is mobile phase), obtains product 22-O-[2-(4-methylbenzamido) ethyl] thioacetylmyulin ( The pure product of compound 3). Yield 36.45%. HR-MS (ESI): CalforC 32 h 45 NO 5 S(M-H+): 556.3091; Found: 556.3118.

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Abstract

The invention belongs to the field of medicinal chemistry, and discloses a pleuromutilin derivative with 2-amino mercaptoethanol side chains and a preparing method and application of the pleuromutilin derivative. The pleuromutilin derivative is a compound shown in the formula 2 and the formula 3 and pharmaceutical salt of the compound. R1, R2 and R3 are independently selected from one of hydrogen atoms, hydroxyl, amino, sulfydryl, hydroxymethyl, amine methyl, nitro, halogen, tri-halogenated methyl radical, methyl, natural amino acid acylamino and alkoxy with the carbon number ranging from 1 to 6. The pleuromutilin compound with the 2-amino mercaptoethanol side chains can well restrain staphylococcus aureus and mycoplasma activity, and is particularly suitable for serving as a novel antibacterial agent to be used for preventing and treating infectious diseases, caused by mycoplasma or multidrug resistance bacterium infection, of people and animals.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a pleuromutilin derivative with a 2-aminoethanethiol side chain, a preparation method and application thereof. Background technique [0002] Mycoplasma is a prokaryotic microorganism similar to bacteria but without a cell wall discovered by Nocard in 1898. It can grow and reproduce on a lifeless artificial medium, with a diameter of 50-300nm and can pass through a bacterial filter. It is the smallest and simplest prokaryote found so far. The number of genes is 480. The only visible organelle in mycoplasma cells is the ribosome. Among human pathogenic mycoplasma, mycoplasma pneumoniae causes pneumonia, mycoplasma hominis, ureaplasma urealyticum and mycoplasma genitalium mainly cause urogenital tract infection; animal treatment mycoplasma often causes infectious diseases of livestock and poultry respiratory system in veterinary clinic. Because it has no cell wall, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/52C07C319/20C07C319/28C07C319/14A61K31/215A61P31/04
Inventor 汤有志黄允真刘雅红张昭圣
Owner SOUTH CHINA AGRI UNIV
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