2-amido-4, 5-diaryl miazines compound, preparation and pharmaceutical use thereof

A technique for diarylpyrimidines and compounds, which is applied in the field of heterocyclic compounds and can solve problems such as weak effects

Inactive Publication Date: 2009-01-14
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007]Natural isoflavone compounds have broad-spectrum biomedical applications, such as genistein, which has obvious anti-tumor, hypolipidemic, anti-atherosclerosis and improvement of women's menopausal symptoms The role of daidzein has anti-arrhythmia, anti-hypoxic-ischemia, antis...

Method used

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  • 2-amido-4, 5-diaryl miazines compound, preparation and pharmaceutical use thereof
  • 2-amido-4, 5-diaryl miazines compound, preparation and pharmaceutical use thereof
  • 2-amido-4, 5-diaryl miazines compound, preparation and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of compound 1

[0038] In this example, first add 7-isopropoxy isoflavone into the reaction kettle, add 100 times the weight of ethanol of 7-isopropoxy isoflavone compound under stirring with a mixer, then add guanidine, 7-isopropoxy The molar ratio of 8-yl isoflavone to guanidine is 1:4, and the temperature of the reaction solution is 80°C with a temperature regulating device. During the reaction, 10% NaOH aqueous solution is continuously added dropwise to keep the pH of the reaction system=8-10, and react for 9 hours , to obtain a mixture of 2-amino-4-(2-hydroxyl-4-isopropoxyphenyl)-5-phenylpyrimidine and unreacted raw materials, the reacted mixture was distilled to dryness under reduced pressure, and then added to the mixture 80 times 3% HCl aqueous solution by weight, heated, dissolved, filtered, adjusted to neutral, left to stand overnight to form a precipitate, filtered under reduced pressure to obtain 2-amino-4-(2-hydroxyl-4-isopropoxyphenyl)- Crude ...

Embodiment 2

[0134] Preparation of Compound 1

[0135] In this example, first add 7-isopropoxy isoflavone into the reaction kettle, add 180 times the weight of 7-isopropoxy isoflavone compound toluene under stirring with a mixer, then add guanidine, 7-isopropoxy The molar ratio of 8-yl isoflavone to guanidine is 1:4, and the temperature of the reaction solution is 100°C with a temperature regulating device. During the reaction, 12% NaOH aqueous solution is continuously added dropwise to keep the pH of the reaction system=8-10, and the reaction is 5 hours , to obtain a mixture of 2-amino-4-(2-hydroxyl-4-isopropoxyphenyl)-5-phenylpyrimidine and unreacted raw materials, the reacted mixture was distilled to dryness under reduced pressure, and the mixture was added 50 times 5% HCl aqueous solution by weight, heated, dissolved, filtered, adjusted to neutral, left standing overnight, a precipitate was formed, filtered under reduced pressure to obtain 2-amino-4-(2-hydroxyl-4-isopropoxyphenyl) - C...

Embodiment 3

[0139] Preparation of Compound 1

[0140] In this example, first add 7-isopropoxy isoflavone into the reaction kettle, add 80 times the weight of methanol of 7-isopropoxy isoflavone compound under stirring with a mixer, then add guanidine, 7-isopropoxy The molar ratio of 8-based isoflavone to guanidine is 1:1, and the temperature of the reaction solution is 50°C with a temperature regulating device. During the reaction, 5% KOH aqueous solution is continuously added dropwise to keep the pH of the reaction system = 8-10, and the reaction is carried out for 30 hours , to obtain a mixture of 2-amino-4-(2-hydroxyl-4-isopropoxyphenyl)-5-phenylpyrimidine and unreacted raw materials, the reacted mixture was distilled to dryness under reduced pressure, and then added to the mixture 110 times 2% HCl aqueous solution by weight, heated, dissolved, filtered, adjusted to neutral, left to stand overnight to form a precipitate, filtered under reduced pressure to obtain 2-amino-4-(2-hydroxyl-4...

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Abstract

Disclosed is a 2-amido-4, 5-diaryl pyridine compound as well as a preparation method and drug purposes thereof, belonging to the heterocyclic compound technique field, and relating to a heterocyclic compound which is heterocyclic and not hydrogenated, contains six rings and takes two nitrogen atoms as exclusive heterocyclic atoms, and does not condense with other rings. An isoflavone is added into a reaction kettle, a solvent and carbamidine are added thereto under agitation, the isoflavone and the carbamidine are present in a molar ratio of 1:1-1:10, with a reaction solution temperature of between 50 and 100 DEG C, an alkaline solution is dripped continuously to make a reaction system have a pH value of 8 to 10, a mixture of 2-substituted-4, 5-diaryl pyridine and matters which do not undergo reaction is obtained after the reaction for 5 to 50 hours, the reaction mixture is distillated to be dry and is added with a 1 to 5 percent HCl aqueous solution with the weight 50 to 130 times that of the mixture, and the crude product of 2-amido-4, 5-diaryl pyridine is obtained through heating, dissolving, filtration, neutrality adjustment, standing, generation of precipitation and filtration, and the crude product is recrystallized with a 50 to 80 percent ethanol solution with the weight 40 to 120 times that of the crude product, so the pure product is acquired.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and specifically relates to a heterocyclic compound containing six-membered rings without hydrogenation, with two nitrogen atoms as the only ring heteroatoms and not fused with other rings. Background technique [0002] Pyrimidine compounds are a class of compounds with a wide range of biological activities, and have always played an important role in biomedicine and heterocyclic pesticides. The biological activity of pyrimidine compounds in medicine is mainly manifested in their anti-tumor and anti-virus effects; they can be used as effective herbicides, insecticides and fungicides in agriculture. Because of their broad application prospects in pharmacology and agrochemicals, the synthesis of pyrimidines has been one of the hotspots in organic synthesis in recent decades. Although natural pyrimidine compounds and their derivatives rarely exist in nature, they have always attracte...

Claims

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Application Information

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IPC IPC(8): C07D239/42A61K31/505A61P25/00
Inventor 张尊听高迷想刘谦光薛东
Owner SHAANXI NORMAL UNIV
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