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4-(4-benzamido phenoxy)-2-(methylcarbamoyl) pyridine derivatives, preparation method and application thereof

The technology of benzamidophenoxy and benzamidophenoxy is applied in the field of chemical medicine and can solve the problems of killing tumor cells and damaging normal cells, low selectivity, toxic and side effects, etc.

Active Publication Date: 2009-02-11
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the low selectivity of existing treatment methods or drugs, some types of normal cells in the body are damaged while killing tumor cells, resulting in obvious toxic and side effects during the treatment process.

Method used

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  • 4-(4-benzamido phenoxy)-2-(methylcarbamoyl) pyridine derivatives, preparation method and application thereof
  • 4-(4-benzamido phenoxy)-2-(methylcarbamoyl) pyridine derivatives, preparation method and application thereof
  • 4-(4-benzamido phenoxy)-2-(methylcarbamoyl) pyridine derivatives, preparation method and application thereof

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preparation example Construction

[0034] 4-(4-aminophenoxy)-2-(methylcarbamoyl)pyridine synthetic methods include the following:

[0035] Method 1: Dissolve p-aminophenol in anhydrous DMF at room temperature, then add potassium tert-butoxide, and stir for 2 hours under nitrogen protection. N-methyl-(4-chloro-2-pyridyl)formamide and potassium carbonate were added, and the reaction was heated for 6 hours. Ethyl acetate and water were poured into the reaction solution at room temperature, the organic layer was collected, dried and spin-dried to obtain a crude product, which was recrystallized to obtain brown crystals.

[0036] Method 2: Dissolve N-methyl-(4-chloro-2-pyridyl)formamide in THF, add p-aminophenol, phase transfer catalyst polyethylene glycol 600, sodium hydroxide and 45% sodium hydroxide solution , Reflux for 12h. THF was distilled off, water was added to the residue, filtered, the filter cake was recrystallized with isopropanol, washed with cold isopropanol, and dried under reduced pressure at 40°C...

Embodiment 1

[0038] Example 1 Preparation of 4-(4-aminophenoxy)-2-(methylcarbamoyl)pyridine

[0039] The synthetic route is as follows:

[0040]

[0041] 1, Preparation of 4-chloro-2-pyridinecarbonyl chloride hydrochloride

[0042] Prepared from 2-formic acid pyridine according to the existing published method, for example: in a dry reaction flask, 2-formic acid pyridine (30.00g, 0.244mmol) and NaBr (4.00g, 0.040mmol) were mixed, then added to chlorine In benzene (40ml), when the suspension was heated to 50°C, thionyl chloride (61ml, 0.840mmol) was slowly added to make the released gas (SO 2, HCl) are effectively controlled. The mixture was heated to 85°C and stirred for 19 hours. After the reaction is completed, cool to 20° C., and remove excess thionyl chloride and chlorobenzene mixture by rotary evaporation. Toluene (65.70g, 75.5ml) was added, and the remaining thionyl chloride and a large amount of chlorobenzene were removed by rotary evaporation again. The obtained crude produc...

Embodiment 2

[0049] Example 2 Preparation of 4-(4-aminophenoxy)-2-(methylcarbamoyl)pyridine

[0050] Dissolve p-aminophenol (0.70 g, 6.40 mmol) in 7 ml of anhydrous DMF at room temperature, add potassium tert-butoxide (0.72 g, 6.40 mmol) and stir for 2 hours under nitrogen protection. N-methyl-(4-chloro-2-pyridyl)formamide (0.50g, 2.90mmol) and potassium carbonate (0.20g, 1.40mmol) were added, and the reaction was heated for 6 hours. The reaction solution was poured into the mixed solution (ethyl acetate 200ml+water 20ml) at room temperature, the organic layer was collected, and the solvent was removed to obtain a crude product, which was separated by column chromatography to obtain 0.41 g of a brown-black solid (57.1% yield).

[0051] 1 H NMR (400MHz, CDCl 3 ): 3.0 (d, J = 5.2Hz, 3H, -NHCH 3 ), 3.7 (br, s, 2H, -NH 2 ), 6.7(d, J=8.8Hz, 2H), 6.9(m, 3H), 7.67(d, J=2.4Hz, 1H), 8.0(s, 1H, NH), 8.3(d, J=6Hz, 1H)

[0052] MS-ESI(m / z): 244.4(M+1), 266.4(M+23)

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Abstract

The invention relates to a derivative of 4-(4-benzoyl amino-phenoxy)-2-(methyl ammonia formyl) pyridine and a preparation method and purposes thereof, belonging to the chemical medicine field. The structure of the derivative is shown as Formula I: R1 is hydrogen, halogenated base, trifluoromethyl, nitro, alkoxy, dimethoxy or amino; R2 is hydrogen, halogenated base, trifluoromethyl, nitro, alkoxy, dimethoxy or amino; R3 is hydrogen, halogenated base, trifluoromethyl, nitro, alkoxy, dimethoxy or amino. The derivative can be used for preparing anti-tumor medicines.

Description

technical field [0001] The invention relates to 4-(4-benzamidophenoxy)-2-(methylcarbamoyl)pyridine derivatives, a preparation method and application, and belongs to the field of chemical medicine. Background technique [0002] Malignant tumors have become the second leading cause of human death, seriously threatening human health. In my country, according to the latest statistics, tumors have become the number one cause of death for our people. According to the latest epidemiological survey data, there are more than 3 million cancer patients in my country, and about 1.3 million patients die of malignant tumors every year. Every year, there are 1.6 to 2 million new cases of malignant tumors, and they are increasing at a rate of 3%, which poses a huge threat to the life and health of our people and brings huge pressure to society and families. To a certain extent, it restricts the sustainable economic development of our country. Traditional tumor treatment methods are mainly m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/81A61K31/44A61P35/00
Inventor 余洛汀赵瀛兰魏于全杨胜勇杨黎
Owner SICHUAN UNIV
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