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Quinoxaline-N1,N4-dioxide derivatives with antimicrobial activity

A technology of dioxide and antibacterial activity, applied in the field of quinoxaline-N1,N4-dioxide derivatives, can solve problems such as toxicity and limit its use

Active Publication Date: 2016-05-25
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen from the above that quinoxaline drugs have unique effects as veterinary antibacterial and growth-promoting drugs. They have been widely used in veterinary clinics, but their potential toxicity limits their use. Therefore, we are looking for better curative effect and lower toxicity. drugs are of great importance

Method used

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  • Quinoxaline-N1,N4-dioxide derivatives with antimicrobial activity
  • Quinoxaline-N1,N4-dioxide derivatives with antimicrobial activity
  • Quinoxaline-N1,N4-dioxide derivatives with antimicrobial activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 2-cyano-3-benzamido-quinoxaline-N 1 ,N 4 -The synthetic reaction formula of dioxide oxide (1) is as follows:

[0042]

[0043] The preparation steps are as follows:

[0044] (1) Add 13.4g (0.1mol) N-benzofurazan oxide, 6.6g (0.1mol) malononitrile and 50mL DMF into a 250mL single-necked flask, stir to dissolve completely, add dropwise 2mL triethylamine, keep 25 ℃, stirred and reacted for 4h, after the reaction was complete, placed at 0°C to cool for 1 hour, filtered with suction, washed the filter cake with 95% ethanol, and dried in vacuo to obtain 2-cyano-3-amino-quinoxaline-N 1 ,N 4 - Dioxide 17.8 g, yield 88%.

[0045] (2) Add 2-cyano-3-amino-quinoxaline-N to a 50mL single-necked flask 1 ,N 4 - Dioxide 2.0g (0.01mol), 30mL dichloromethane, 1mL pyridine, stirred and dissolved, then added dropwise 1.4g (0.01mol) of benzoyl chloride, stirred at 25°C for 2 hours. The reaction solution was distilled off the solvent under reduced pressure, and then 20 mL of ethyl ...

Embodiment 2

[0047] 2-cyano-3-p-methylbenzamido-quinoxaline-N 1 ,N 4 -The synthesis reaction formula of dioxide oxide (2) is as follows:

[0048]

[0049] The preparation steps are as follows:

[0050] The benzoyl chloride in embodiment 1 is changed into p-methylbenzoyl chloride, and other reaction conditions are with embodiment 1, obtain 2-cyano group-3-p-methylbenzamido-quinoxaline-N 1 ,N 4 - Dioxide 2.65 g, 72% yield in two steps. Melting point 218.2-220.5℃; MS: [M+H] + 321.0920;IR(KBr)υcm -1 : 3420, 3253, 3083, 2224 (weak), 1675, 1526, 1335; 1 HNMR (DMSO-d 6 ,400MHz) δppm: 8.53~8.65(q,2H,H 5 +H 8 ), 7.84~7.92(m,2H,H 6 +H 7 ), 7.31~7.33(d,2H,Ar--H 2’ +H 6’ ), 7.09~7.11 (d,2H,Ar-H 3’ +H 5’ ),2.30(s,3H,-CH 3 ).

Embodiment 3

[0052] 2-cyano-3-p-fluorobenzamido-quinoxaline-N 1 ,N 4 -The synthetic reaction formula of dioxide oxide (3) is as follows:

[0053]

[0054] The preparation steps are as follows:

[0055] The benzoyl chloride in embodiment 1 is changed into p-fluorobenzoyl chloride, and other reaction conditions are with embodiment 1, obtain 2-cyano group-3-p-fluorobenzamido-quinoxaline-N 1 ,N 4 - Dioxide 2.73 g, 74% yield in two steps. Melting point 208.5-210.5℃; MS: [M+H] + 325.0772;IR(KBr)υcm -1 : 3435, 3243, 3080, 2225 (weak), 1685, 1525, 1337; 1 HNMR (DMSO-d 6 ,400MHz) δppm: 8.57~8.63(q,2H,H 5 +H 8 ), 7.92~7.94(m,2H,H 6 +H 7 ), 7.84~7.88(d,2H,Ar-H 3’ +H 5’ ), 7.07~7.11(t,2H,Ar--H 2’ +H 6’ ).

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Abstract

The invention belongs to the technical field of pharmaceutical chemosynthesis, and particularly relates to quinoxaline-N1,N4-dioxide derivatives with antimicrobial activity. The invention also relates to preparation of the derivatives and antimicrobial activity testing of the derivatives. The new synthetic compounds are prepared by the following steps: carrying out Beirut reaction on the raw material N-benzofuroxan oxide and malononitrile under alkaline conditions to obtain 3-amino-2-cyano-quinoxaline-N1,N4-dioxide, and reacting with appropriate acyl chloride to obtain a series of 2-cyano-amidoquinoxaline-N1,N4-dioxides. The in-vitro antibacterial activity test result indicates that the quinoxaline-N1,N4-dioxide derivatives have favorable antibacterial activity for mycobacterium hominis and mycobacterium bovis and also have antibacterial activity for Staphylococcus aureus, Streptococcus pneumoniae and Pasteurella. The invention also discloses a structural formula of the compounds used as a target antibacterial drug.

Description

technical field [0001] The invention belongs to the technical field of veterinary drug synthesis, in particular to quinoxaline-N with antibacterial activity 1 ,N 4 - Dioxide derivatives. The invention also includes the preparation of the derivative and its antibacterial activity test. Among them, the newly synthesized compound is based on N-benzofurazan oxide as raw material, and undergoes Beirut reaction with malononitrile under alkaline conditions to obtain 3-amino-2-cyano-quinoxaline-N 1 ,N 4 The -dioxide is then reacted with a suitable acid chloride to obtain a series of 2-cyano-3-amidoquinoxaline-N 1 ,N 4 - Dioxide. In vitro antibacterial activity test results show that: it has good antibacterial activity against human Mycobacterium tuberculosis and Mycobacterium bovis; it has antibacterial activity against Staphylococcus aureus, Streptococcus pneumoniae, Escherichia coli and Pasteurella. Background technique [0002] Quinoxaline compounds are an important class ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/52C07D401/12A61K31/498A61P31/06A61P31/04
CPCC07D241/52C07D401/12
Inventor 袁宗辉潘源虎戴梦红李盼盼谢书宇陶燕飞陈冬梅黄玲利王玉莲王旭彭大鹏刘振利
Owner HUAZHONG AGRI UNIV
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