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Quinazolone anti-coccidia compound containing 1-methoxy-naphthyl

A technology of quinazolinone and methoxynaphthyl, applied in the field of quinazolinone anticoccidial compounds, which can solve the problems of less application of quinazolinone anticoccidial compounds, complex synthesis, and large-scale use

Inactive Publication Date: 2009-12-23
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, the use of quinazolinone anticoccidial compounds is relatively low compared to other classes of coccidiostats
The only quinazolinone anticoccidiostats sold on the market is hemosanone, and because the synthesis of this compound is complex, the synthesis of the piperidinylbromoketone part requires more than ten steps, resulting in high production costs. Affected its large-scale use
Therefore, it is necessary to find some quinazolinone compounds with relatively simple structure and low cost with anticoccidial activity to solve the problem of drug rotation in the current process of coccidiosis control

Method used

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  • Quinazolone anti-coccidia compound containing 1-methoxy-naphthyl
  • Quinazolone anti-coccidia compound containing 1-methoxy-naphthyl
  • Quinazolone anti-coccidia compound containing 1-methoxy-naphthyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Synthesis of 6-fluoro-3-(2-(1-methoxynaphthalen-2-yl)-2-oxo-ethyl)-4-(3H)-quinazolinone

[0029] Add 1.64g of 6-fluoro-4-(3H)-quinazolinone into a 100mL three-neck flask, dissolve it in 10mL of DMSO, then add 0.48g of NaH and 0.10g of potassium iodide in sequence; after stirring for 5min, start to add the dissolved 2.79g of 2-bromo-1-(1-methoxynaphthalene-2-yl)ethanone in 5mL DMSO solution, after dripping, react at 70°C for 3h; after the reactant is cooled, add water for suction filtration, and reconstitute the crude product with absolute ethanol Crystallized twice to obtain 1.85 g of yellow powdery solid with a yield of 51%.

[0030] mp: 163-166°C; 1 H NMR (400MHz, CDCl 3 , δppm): 8.25(dd, 1H, J=7.6Hz, 1.6Hz), 7.98(s, 1H), 7.95(dd, 1H, J=8.4Hz, 2.4Hz), 7.91(dd, 1H, J=6.8 Hz, 2.0Hz), 7.85(d, 1H, J=8.8Hz), 7.80-7.76(m, 1H), 7.69(d, 1H, J=8.8Hz), 7.67-7.61(m, 2H), 7.51( ddd, 1H, J=8.8Hz, 8.0Hz, 2.8Hz).5.55(s, 2H), 4.20(s, 3H); IR(KBr, cm -1 ): 3059, 2960, ...

Embodiment 2

[0031] Example 2: Synthesis of 6-iodo-3-(2-(1-methoxynaphthalen-2-yl)-2-oxo-ethyl)-4-(3H)-quinazolinone

[0032] Add 2.45g of 6-iodo-4-(3H)-quinazolinone into a 100mL three-necked flask, dissolve it in 10mL of DMSO, then add 0.48g of NaH and 0.10g of potassium iodide in sequence; after stirring for 5min, start to add the dissolved 2.79g of 2-bromo-1-(1-methoxynaphthalene-2-yl)ethanone in 5mL DMSO solution, after dripping, react at 75°C for 3h; after the reactant is cooled, add water for suction filtration, and reconstitute the crude product with absolute ethanol Crystallized twice to obtain 3.15 g of yellow powdery solid, yield: 67%.

[0033] mp: 162-164°C; 1 H NMR (400MHz, CDCl 3 , δppm): 8.66(d, 1H, J=2.0Hz), 8.25(dd, 1H, J=7.2Hz, 1.6Hz), 8.05(dd, 1H, J=8.8Hz, 1.6Hz), 8.01(s, 1H), 7.90(dd, 1H, J=7.2Hz, 2.0Hz), 7.84(d, 1H, J=8.8Hz), 7.69(d, 1H, J=8.8Hz), 7.66-7.63(m, 2H) , 7.50 (d, 1H, J=8.8Hz), 5.54 (s, 2H), 4.19 (s, 3H); IR (KBr, cm -1 ): 2949, 2849, 1675, 1607, 1565, ...

Embodiment 3

[0034] Example 3: Preparation of 3-(2-(1-methoxynaphthalen-2-yl)-2-oxo-ethyl)-4-(3H)-quinazolinone

[0035]Add 1.46g of 4-(3H)-quinazolinone to a 100mL three-necked flask, dissolve it in 10mL of DMSO, then add 0.48g of NaH and 0.10g of potassium iodide in sequence. After stirring for 5 minutes, 2.79 g of 2-bromo-1-(1-methoxynaphth-2-yl)ethanone was dissolved in 5 mL of DMSO solution dropwise, and the reaction was carried out at 75°C for 2 hours. After the reactant was cooled, water was added and suction filtered, and the crude product was recrystallized with absolute ethanol to obtain 1.79 g of white powdery solid with a yield of 52%. mp: 151-153°C; 1 H NMR (400MHz, CDCl 3 , δppm): 8.33 (d, 1H, J = 8.0Hz), 8.26 (dd, 1H, J = 7.2Hz, 2.0Hz), 8.02 (s, 1H), 7.90 (dd, 1H, J = 6.8Hz, 2.4 Hz), 7.86(d, 1H, J=8.4Hz), 7.82-7.76(m, 2H), 7.69(d, 1H, J=8.8Hz), 7.67-7.61(m, 2H), 7.53(ddd, 1H , J=8.0Hz, 8.4Hz, 2.0Hz), 5.56(s, 2H), 4.20(s, 3H); IR(KBr, cm -1 ): 2961, 2850, 1674, 1610, 156...

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Abstract

The invention relates to a quinazolone compound containing 1-methoxy-naphthyl expressed in a structural general formula I, a synthesis method and applications thereof; and 2-bromine-1-(1-methoxy-naphthyl-2-radical) butanone and replaced quinazolone directly react to obtain the compound which has lower cost, is easy to be synthesized, and can prevent and treat coccidiosis in chicken.

Description

technical field [0001] The present invention relates to a class of quinazolinone anticoccidial compounds containing 1-methoxynaphthyl. Background technique [0002] Chicken coccidiosis is caused by one or several single-celled parasitic protozoa of Sporozoa, Eimeriaceae, and Eimeria parasitizing on chicken intestinal epithelial cells, causing diarrhea, bloody stool, growth retardation, and feed conversion. It is a parasitic disease characterized by reduced mortality and death, which is one of the diseases that currently cause heavy losses in the intensive chicken industry. For a long time, the systematic addition of drugs to feed has been a routine method for controlling coccidiosis in the aquaculture industry. However, due to the large amount of anticoccidial drugs used in the world, the area of ​​use is wide, and the application period is long, so far, coccidia can produce drug resistance to almost all drugs, and often show multi-drug resistance and cross-drug resistance ...

Claims

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Application Information

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IPC IPC(8): C07D239/88A61K31/517A61P33/02
Inventor 王玉良张园园陈广民张帅薛黎明刘庆辉刘建新王玉忠
Owner SICHUAN UNIV