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Pleuromutilin derivatives with piperazine side chain, and preparation method and application thereof

A technology for pleuromutilin and derivatives, which is applied in the field of pleuromutilin derivatives and its preparation, can solve the problem of rare drug-resistant bacteria, achieve good in vitro antibacterial activity and low preparation cost

Active Publication Date: 2016-08-10
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 derivatives with piperazine side chain, and preparation method and application thereof
  • Pleuromutilin derivatives with piperazine side chain, and preparation method and application thereof
  • Pleuromutilin derivatives with piperazine side chain, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis of 14-O-[4-(2-oxomethylphenyl)piperazin-1-yl]acetyl muulin (compound 1)

[0048]0.481g (0.905mmol) of intermediate I was dissolved in 10ml of acetonitrile, 0.203g (1.36mmol) of sodium iodide and 0.125g (0.905mmol) of potassium carbonate were added, and heated to reflux for 1 hour. Dissolve 0.192g (1.00mmol) of 1-(2-oxomethylphenyl)piperazine in 10ml of acetonitrile, slowly add to the above mixed solution and continue to heat and reflux for 2h, transfer the reaction solution to a separatory funnel after reaction, and add 3. Take 50ml of water, 50ml of chloroform, shake, let stand to separate layers, take the organic phase, dehydrate it with anhydrous sodium sulfate, evaporate the organic solvent under reduced pressure, and obtain the crude product as a solid. The solid was dissolved with 5 ml of ethyl acetate, and thoroughly mixed with 1 g of 200-300 mesh silica gel powder for chromatography. After the natural evaporation of ethyl acetate, the above...

Embodiment 2

[0049] Example 2: Synthesis of 14-O-[4-(3-oxomethylphenyl)piperazin-1-yl]acetyl muulin (compound 2)

[0050] 0.481g (0.905mmol) of intermediate I was dissolved in 10ml of acetonitrile, 0.203g (1.36mmol) of sodium iodide and 0.125g (0.905mmol) of potassium carbonate were added, and heated to reflux for 1 hour. Dissolve 0.192g (1.00mmol) of 1-(3-oxymethylphenyl)piperazine in 10ml of acetonitrile, slowly add to the above mixed solution and continue to heat and reflux for 2h, transfer the reaction solution to a separatory funnel after reaction, and add Mix 50ml of water and 50ml of chloroform, shake, let stand to separate layers, take the organic phase, dehydrate it with anhydrous sodium sulfate, evaporate the organic solvent under reduced pressure, and obtain the crude product as a solid. The solid was dissolved with 5 ml of ethyl acetate, and thoroughly mixed with 1 g of 200-300 mesh silica gel powder for chromatography. After the natural evaporation of ethyl acetate, the above...

Embodiment 3

[0051] Example 3: Synthesis of 14-O-[4-(4-oxomethylphenyl)piperazin-1-yl]acetyl muulin (compound 3)

[0052] 0.481g (0.905mmol) of intermediate I was dissolved in 10ml of acetonitrile, 0.203g (1.36mmol) of sodium iodide and 0.125g (0.905mmol) of potassium carbonate were added, and heated to reflux for 1 hour. Dissolve 0.192g (1.00mmol) of 1-(4-oxymethylphenyl)piperazine in 10ml of acetonitrile, slowly add to the above mixture and continue to heat and reflux for 2h, transfer the reaction solution to a separatory funnel after reaction, and add Mix 50ml of water and 50ml of chloroform, shake, let stand to separate layers, take the organic phase, dehydrate it with anhydrous sodium sulfate, evaporate the organic solvent under reduced pressure, and obtain the crude product as a solid. The solid was dissolved with 5 ml of ethyl acetate, and thoroughly mixed with 1 g of 200-300 mesh silica gel powder for chromatography. After the natural evaporation of ethyl acetate, the above crude ...

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Abstract

The invention belongs to the field of pharmaceutical chemistry, and discloses pleuromutilin derivatives with piperazine side chain, and a preparation method and application thereof. The derivatives have the structure disclosed as Formula 2 or Formula 3, wherein R1 is hydrogen atom, methoxy, methyl, hydroxy, nitro or chlorine atom; R2 is hydrogen atom, methoxy, methyl, hydroxy, nitro or chlorine atom; R3 is hydrogen atom, methoxy, methyl, hydroxy, nitro or chlorine atom; and R4 is phenyl or methyl. The pleuromutilin derivatives with piperazine side chain have favorable in-vitro antimicrobial activity, have the advantage of lower preparation cost than valnemulin and retapamulin, and thus, are specially suitable to be used as a novel antibacterial drug for preventing and treating human or animal bacterial infective diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a pleuromutilin derivative with a piperazine side chain, a preparation method and application thereof. Background technique [0002] The emergence of "superbugs" such as vancomycin-resistant enterococci (VRE), multidrug-resistant tuberculosis (MDR-TB), multidrug-resistant Streptococcus pneumoniae (MDRSP) and methicillin-resistant Staphylococcus aureus (MRSA), When people face this type of bacterial infectious disease, they are almost in a situation where there is no cure. In response to the increasingly serious problem of drug resistance, humans have been trying to find and develop antibacterial drugs with new antibacterial mechanisms. [0003] Pleuromutilin (Formula 1) is produced by higher fungi Pleurotusmutiliz (Fr.) Sacc. and Pleurotus Passeckeranius Pilat, a tricyclic diterpene compound with a parallel (5-6-8) tricyclic ring. Studies have shown that the targe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/15A61K31/495A61P31/04
CPCC07D295/15
Inventor 刘雅红骆健汤有志廖晓萍孙坚
Owner SOUTH CHINA AGRI UNIV
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