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3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide as well as preparation method and application thereof

A technology of styryl ketone and dioxide, applied in the field of quinoxaline compounds

Inactive Publication Date: 2014-04-16
河北美荷药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Nevertheless, the application of quinoxalines currently used in feed has certain risks after all. If there are economical, safe and effective substitutes to maintain high-efficiency livestock and poultry production, it will be the most ideal solution that people expect

Method used

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  • 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide as well as preparation method and application thereof
  • 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide as well as preparation method and application thereof
  • 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Preparation of 3-methyl-2-(o-aminostyryl)-quinoxaline-1,4-dioxide

[0062] The structural formula is as follows:

[0063]

[0064] R is an amine group.

[0065] Its preparation method is:

[0066] 1) Synthesis of benzofurazan

[0067]

[0068] Dissolve o-nitroaniline (40g, 0.29mol) in 225ml of methanol solution, add 21g of NaOH, stir until completely dissolved, slowly add 250ml of NaClO with a concentration of 1mol / L in an ice-water bath for about half an hour, continue stirring at room temperature for 2h, TLC Follow-up detection showed that a light yellow solid was continuously precipitated, and 300ml of water was added, the solid was filtered out with suction, washed with water and dried to obtain an orange-yellow crude product, which was recrystallized from 70% ethanol to obtain yellow flaky crystals. Yield 33g, 83% yield.

[0069] 1HNMR(CDCl3)δppm: 7.81-7.90(m, 2 H),8.55-8,58(d, 1 H),8.62-8.64(d, 1 H);

[0070] 13 CNMR (CDCl3) δppm: 113.3, 114.7, 118....

Embodiment 2

[0083] Preparation of 3-methyl-2-(m-aminostyryl)-quinoxaline-1,4-dioxide

[0084] The structural formula is as follows:

[0085]

[0086] R is an amine group.

[0087] Its preparation method is the same as that of Example 1 with reference to Example 1, the difference is that 3-aminobenzaldehyde is used in step 3).

[0088]

[0089] Compound b is finally obtained.

[0090] For the proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the final product compound b, see Figure 5 , 6 .

Embodiment 3

[0092] Preparation of 3-methyl-2-(p-aminostyryl)-quinoxaline-1,4-dioxide

[0093] The structural formula is as follows:

[0094]

[0095] R is an amine group.

[0096] Its preparation method is basically the same as that of Example 1, except that 4-aminobenzaldehyde is used in step 3).

[0097]

[0098] Compound c is finally obtained.

[0099] For the proton nuclear magnetic resonance spectrum and carbon nuclear magnetic resonance spectrum of the final product compound c, see Figure 7 , 8 .

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Abstract

The invention discloses 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide and a preparation method thereof. 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide (a, b, c) are generated through performing aldol condensation on mequindox and amino benzaldehyde by adopting a one-step method. An activity experiment on the 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide shows that the 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide has good bacteriostatic activity for the resistance to escherichia coli, salmonella, pseudomonas aeruginosa, and klebsiella. According to the invention, the prepared 3-methyl-2-(amino styrene ketone)-quinoxaline-1, 4-dioxide can be used as an antibacterial veterinary drug feed additive with the growth promotion function for livestock.

Description

technical field [0001] The invention relates to a quinoxaline compound, its preparation method and antibacterial activity. Background technique [0002] Quinoxaline-1,4-dioxyl derivatives as antibacterial and growth-promoting additives have low toxicity, small side effects, low dosage, and can be used in feed for a long period of time, playing a huge role in animal husbandry. For example, Carbadox, Olaquindox, and Maquindox have good activity on Gram-negative bacteria and positive bacteria, and have nitrogen retention and protein assimilation effects, which are helpful for improving feed conversion. It has a significant effect on rate and growth promotion. Therefore, it is widely used in various animal feeds, mainly used to promote growth, improve feed utilization rate and prevent diarrhea in young animals, improve the survival rate of young animals and poultry, and sometimes it is also used to treat fowl cholera, pullorum, piglet diarrhea and other diseases . Since Hadda...

Claims

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Application Information

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IPC IPC(8): C07D241/42A61K31/498A61P31/04A61P3/00
CPCC07D241/52
Inventor 孟凡桥梁剑平陶蕾赵凤舞贾忠
Owner 河北美荷药业有限公司