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Five-membered heterocyclic dicarbonyl derivative and applications thereof for resisting multidrug-resistant bacteria

A kind of use and pharmaceutical technology, applied in the direction of antibacterial drugs, active ingredients of heterocyclic compounds, organic compounds, etc., to achieve the effect of anti-multidrug-resistant bacterial infection

Inactive Publication Date: 2015-05-06
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But even if used in combination, these compound preparations are not all effective for all drug-resistant bacteria, especially for NDM-1 enzymes, there is no effective inhibitor report, so developing new inhibitors has become the current microbial pharmacy, computer-aided drug Active field in related disciplines such as design and medicinal chemistry

Method used

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  • Five-membered heterocyclic dicarbonyl derivative and applications thereof for resisting multidrug-resistant bacteria
  • Five-membered heterocyclic dicarbonyl derivative and applications thereof for resisting multidrug-resistant bacteria
  • Five-membered heterocyclic dicarbonyl derivative and applications thereof for resisting multidrug-resistant bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 4-Methyl-2-acetyl-5-propionyl-3-hydroxyfuran (CPU-ZH003)

[0046]Add 9ml (0.1mol) of propionyl chloride, 8.8ml (0.1mol) of 1-hydroxy-2-butanone and 14g of potassium carbonate (0.1mol) into a 100ml three-necked bottle, stir electromagnetically, and react under reflux at 80°C for 6 hours. Raise the reaction temperature to 110°C, slowly drop 8.5ml (0.1mol) of 2-oxopropionic acid into the reaction solution, and continue the reaction for 10 hours after the addition. Suction filtration, the reaction solution was concentrated under reduced pressure, and the remaining liquid was extracted with ethyl acetate. Concentrate and dry to obtain 10.56 g of solid, with a total yield of 53.86%.

[0047] Molecular formula: C 10 h 12 o 4 , molecular weight: 196.20

[0048] MS (EI) m / z 196.

[0049] 1 H-NMR (AV-500, δ, DMSO-d 6 ): 1.15(t,3H); 1.92(s,3H); 2.48(s,3H); 3.75(q,2H); 5.40(s,1H)

Embodiment 2

[0051] 3-((1-H-1,2,4-Triazolyl)methylene)-2-acetyl-3-hydroxy-pyrrolecarboxylic acid (CPU-ZH008)

[0052] Add 11.6g (0.1mol) of sodium chloroacetate, 7.5ml (0.1mol) of 1-amino-2-propanone and 14g of potassium carbonate (0.1mol) into a 100ml three-necked flask, stir it electromagnetically, and reflux at 95°C for 6 hours , raise the reaction temperature to 110°C, slowly drop 15g (0.1mol) of 1-H-1,2,4-triazolyl-2-oxopropionic acid into the reaction liquid, react overnight, add concentrated hydrochloric acid to The pH of the solution was about 4.0. Suction filtration, the reaction solution was concentrated under reduced pressure, and the remaining liquid was extracted with a mixed organic solvent of ethyl acetate: chloroform = 3:1. Concentrate and dry to obtain 18.14 g of solid, with a total yield of 71.13%.

[0053] Molecular formula: C 10 h 10 N 4 o 4 , molecular weight: 250.22

[0054] MS (EI) m / z 249 (M-1).

[0055] 1 H-NMR (AV-500, δ, DMSO-d 6 ):2.08(t,3H);5.02(s,1H)...

Embodiment 3

[0057] Dimethyl 3,4-dibenzyloxy-2,5-thiophenedicarboxylate (CPU-ZH016)

[0058] Add 8ml (0.1mol) of acetyl chloride, 0.1mol of 1-mercapto-2-acetone, 200ml of DMF and 14g of potassium carbonate (0.1mol) into a 250ml three-necked bottle, stir with electromagnetic force, react at 40°C for 3 hours, and raise the reaction temperature At 85°C, 27 g (0.1 mol) of dibenzyl oxalate was slowly added to the reaction liquid, and the reaction was carried out for 5 hours. Suction filtration, the reaction solution was concentrated under reduced pressure, and the remaining liquid was extracted with chloroform. Concentrate and dry to obtain 20.14 g of solid, with a total yield of 53.02%.

[0059] Molecular formula: C 22 h 20 o 6 S, molecular weight: 412.47

[0060] MS (EI) m / z 435.1 (M+23)

[0061] 1 H-NMR (AV-500, δ, DMSO-d 6 ): 3.00(s,3H); 5.16(s,2H); 7.24-7.41(m,5H); 7.83(s,2H)

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Abstract

The invention relates to the field of medicinal chemistry, and particularly relates to a five-membered heterocyclic dicarbonyl derivative (I) and applications thereof for resisting multidrug-resistant bacteria. Proved by pharmacological tests, the compound is jointly combined with antibiotics, thus having better inhibition effect on the multidrug-resistant bacteria.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of five-membered heterocyclic biscarbonyl derivatives and their application in anti-multidrug-resistant bacteria. Background technique [0002] Antibiotics are a class of antibacterial and microbial drugs that are widely used clinically and used in large quantities. Since penicillin was used clinically in 1940, it has played an important role in controlling and treating diseases. At present, there are many kinds of antibacterial and microbial drugs used clinically, but with the large number of antibiotics, they are widely used, especially in clinical irrational application, and even abused, which eventually leads to the emergence of a large number of drug-resistant bacteria. In particular, the recent emergence of NDM-1 super bacteria has attracted global attention and tension. Metallo-1, NDM-1) is famous, the gene produces a special β-lactamase, its activity requires t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/58C07D403/06C07D333/38C07D307/68C07D333/36C07F9/38C07C221/00C07C225/20A61K31/407A61K31/135A61K31/34A61K31/4196A61K31/381A61K31/496A61K31/67A61P31/04
Inventor 郑珩沈秉正劳兴珍周亚丽
Owner CHINA PHARM UNIV
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