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3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide, and preparation method and application thereof

A methoxy styryl ketone-based, dioxide technology, applied in the field of quinoxaline compounds, can solve the problems of poor curative effect, excessive drug residues, abuse of antibacterial drugs and the like

Inactive Publication Date: 2014-03-26
河北美荷药业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, due to the single variety of veterinary drugs and poor curative effect, the abuse of antibacterial drugs in animal husbandry production is very serious, and the drug resistance of bacteria is greatly enhanced, which makes it difficult to control many bacterial diseases, and drug residues in animal products seriously exceed the standard
Therefore, in order to meet the severe domestic and foreign market competition that our country is facing, solve the problems of single species and lack of independent intellectual property rights products in the research and development of new veterinary drugs and feed additives in our country, and research and develop new-type products with good application prospects and domestic and foreign market competitiveness. Veterinary drugs and feed additives are imminent

Method used

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  • 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide, and preparation method and application thereof
  • 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide, and preparation method and application thereof
  • 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0150] Preparation of 3-methyl-2-(o-methoxystyryl)-quinoxaline-1,4-dioxide

[0151] The structural formula is as follows:

[0152]

[0153] R is methoxy.

[0154] Its preparation method is:

[0155] 1) Synthesis of benzofurazan

[0156]

[0157] 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.

[0158] 1HNMR (CDCl3) δppm: 7.81-7.90 (m, 2H), 8.55-8, 58 (d, 1H), 8.62-8.64 (d, 1H); 13CNMR (CDCl3) δppm: 113.3, 114.7, 118.2, 132.4, 133.8...

Embodiment 2

[0168] Preparation of 3-methyl-2-(m-methoxystyryl)-quinoxaline-1,4-dioxide

[0169] The structural formula is as follows:

[0170]

[0171] R is methoxy.

[0172] Its preparation method is the same as in Example 1, referring to Example 1, except that 3-methoxybenzaldehyde is used in step 3).

[0173]

[0174] Compound b is finally obtained. Light yellow powder 1.685g, yield 52%. 1H NMR (400MHz, DMSO-d6) δ: 9.70(s, 1H), 8.52(d, J=5.6Hz, 1H), 8.43(d, J=5.6Hz, 1H), 7.98(s, 2H), 7.78( d, J=16Hz, 3H), 7.24~7.10(m, 4H), 6.89(s, 1H), 2.34(s, 3H).

[0175] 13CNMR(400MHz,DMSO-d6)δ:187.28,157.76,149.19,138.93,138.57,137.66,136.71,135.31,132.40,131.43,130.05,125.30,120.15,119.64,119.64,118.82,117,10,115.40,13.99。

Embodiment 3

[0177] Preparation of 3-methyl-2-(p-methoxystyryl)-quinoxaline-1,4-dioxide

[0178] The structural formula is as follows:

[0179]

[0180] R is methoxy.

[0181] Its preparation method is basically the same as that of Example 1, except that 4-methoxybenzaldehyde is used in step 3).

[0182]

[0183] Compound c is finally obtained. Light yellow powder 1.366g, yield 42%. 1HNMR (400MHz, DMSO-d6) δ: 10.31(s, 1H), 8.52~8.43(m, 2H), 7.98(s, 2H), 7.74(d, J=14.4Hz,, 3H), 7.61(s, 2H), 7.01(d, J=14.8Hz, 1H), 6.81(s, 2H), 2.35(s, 3H).

[0184] 13CNMR (400MHz, DMSO-d6) δ: 187.35, 161.65, 150.38, 139.32, 138.00, 137.18, 135.51, 132.74, 132.00, 131.83, 129.81, 125.55, 122.58, 120.11, 117.4491, 114

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Abstract

The invention discloses 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide and a preparation method thereof. Mequindox and methoxy benzaldehyde are subjected to aldol condensation to generate 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide by adopting a one-step method. Active experiments indicate that 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide has good bacteriostasis activity against escherichia coli, staphylococcus aureus, pseudomonas aeruginosa, bacillus subtilis and the like. Through studies on growth promotion and drug residues, 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide (a) has relatively good effect of promoting growth, and is safe to use. The prepared 3-methyl-2-(methoxy styrene keto)-quinoxaline-1,4-dioxide (a) can be used as a livestock and poultry antibacterial growth-promoting veterinary drug feed additive and can be widely applied.

Description

technical field [0001] The present invention relates to a quinoxaline compound, its preparation method and its application in medicine. Background technique [0002] With the continuous improvement of the scale of animal husbandry production in my country, the demand for non-nutritive pharmaceutical feed additives with high efficiency, low toxicity and low residue is increasing rapidly. According to incomplete statistics, the total amount of livestock and poultry breeding in my country accounts for 1 / 4 of the world's total, while the total production value of veterinary drugs in my country in the same year only accounts for 1 / 10 of the world's total output value of veterinary drugs, which is extremely disproportionate to my country's status as a large breeding country . More than 68 kinds of veterinary drugs (excluding vaccines) are imported by the Ministry of Agriculture every year, which indicates that the development and research of veterinary drugs in my country is serio...

Claims

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Application Information

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IPC IPC(8): C07D241/52A61P31/04A23K1/17A23K1/16A23K20/195
CPCA23K20/137A23K20/195C07D241/52
Inventor 孟凡桥梁剑平陶蕾贾忠张铎郝宝成赵凤舞
Owner 河北美荷药业有限公司
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