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Piperazine urea pleuromutilin derivative and application thereof

A technology of pleuromutilin and its derivatives, applied in medical preparations containing active ingredients, organic active ingredients, organic chemistry, etc., can solve the problem that the antibacterial effect does not have much advantage

Active Publication Date: 2020-10-20
XIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compound has good antibacterial activity of inhibiting Staphylococcus aureus and mycoplasma activity, but compared with the existing antibacterial drugs such as tiamulin, the compound does not have much advantage in antibacterial effect in vitro

Method used

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  • Piperazine urea pleuromutilin derivative and application thereof
  • Piperazine urea pleuromutilin derivative and application thereof
  • Piperazine urea pleuromutilin derivative and application thereof

Examples

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Embodiment 1

[0059] The synthesis of embodiment 1 compound 6a-v

[0060] Compounds 6a-v were synthesized according to the following synthetic route:

[0061]

[0062] Reagents and reaction conditions: (i) TsCl, triethylamine, DCM, 25°C; (ii) piperazine, K 2 CO 3 , NaI, THF, reflux; (iii) 9a~e, NaI, K 2 CO 3 ,MeCN,70℃; (iv)10f~u,K 2 CO 3 ,DMF,80℃; (v)11,DMAP,MeCN,70℃; (vi)SnCl 2 , EtOH, reflux; (vii) TFA, DCM, 25°C; (viii) (1) CDI, triethylamine, N-Bocpiperazine, MeCN and DMF, 25°C for 9a and 9b, or BTC, triethylamine, N-Boc Piperazine, THF and DCM, 25°C for 9c~e, (2) TFA, DCM, 25°C; (ix) Trichloroacetyl chloride, triethylamine, DCM, 25°C; (x) 4-nitrophenyl carbon Acid chloride, NMM, DCM, 25℃.

[0063] Synthesis of Compound 7:

[0064] Dissolve p-toluenesulfonyl chloride (1.91g, 10.0mmol) and pleuromutilin (3.56g, 9.4mmol) in DCM (10mL), then add triethylamine (4.54g, 12.0mmol), and react at room temperature for 20h. After the reaction was completed, water (50mL) was added, and...

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Abstract

The invention relates to a piperazine urea pleuromutilin derivative and application thereof, belonging to the technical field of antibacterial drugs. The technical problem to be solved by the invention is to provide the piperazine urea pleuromutilin derivative with good antibacterial activity. The structural formula of the piperazine urea pleuromutilin derivative is shown as a formula I in the specification. The piperazine urea pleuromutilin derivative disclosed by the invention is novel in structure and has excellent antibacterial activity. An in-vitro antibacterial experiment obviously showsthat the piperazine urea pleuromutilin derivative has an excellent antibacterial effect on standard drug-resistant staphylococcus aureus strains ATCC33591 and ATCC43300, and on escherichia coli strains ATCC25922 and ATCC25923, is expected to be applied to treatment of bacterial infection caused by staphylococcus aureus and escherichia coli, and provides a new choice for anti-infective drugs.

Description

technical field [0001] The invention relates to piperazinurea pleuromutilin derivatives and uses thereof, belonging to the technical field of antibacterial drugs. Background technique [0002] The discovery of antibiotics is of great significance in the history of human development, but now due to the widespread and long-term abuse of antibiotics in clinical practice, bacterial drug resistance is becoming more and more serious, which undoubtedly poses a huge threat to human life. In order to cope with the dilemma of decreasing effective antibacterial drugs and increasing drug-resistant bacteria, it is urgent to find an effective way to solve this thorny global problem. Facing the deteriorating trend, in 2012, the U.S. Food and Drug Administration (FDA) launched an incentive program (generating antibiotics incentives now, GAIN) aimed at promoting antibiotic research and development. Nearly 70% of anti-infective (anti-bacterial, anti-fungal, anti-parasitic and anti-viral) dru...

Claims

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Application Information

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IPC IPC(8): C07D295/192C07D215/38C07D213/75C07D295/215A61K31/495A61K31/496A61K31/5377A61P31/04
CPCC07D295/192C07D215/38C07D213/75C07D295/215A61P31/04Y02A50/30
Inventor 张园园吴春霞谢川雍灿余江林刘阳商凤
Owner XIHUA UNIV
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