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4,5-diarylpyrimidinethiourea compounds and pharmaceutical uses

A technology of diaryl pyrimidine thiourea and pyrimidine thiourea is applied in the field of heterocyclic compounds and can solve the problems of low yield, few synthesis methods of pyrimidine thiourea compounds and the like

Inactive Publication Date: 2012-02-22
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few synthetic methods for pyrimidinethiourea compounds. According to literature reports, people such as Nguyen Dinh have synthesized compound 4,6-diaryl-2-pyrimidinylthiourea derivatives, which are based on chalcone, guanidine, polyacetyl -D-glucopyranosyl isocyanate is the reaction raw material, synthesized by two steps, and the yield is relatively low (60%) (Thanh, Nguyen Dinh; Mai, Nguyen Thi Thanh.Carbohydr.Res.2009,344(17), 2399 -2405.)

Method used

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  • 4,5-diarylpyrimidinethiourea compounds and pharmaceutical uses
  • 4,5-diarylpyrimidinethiourea compounds and pharmaceutical uses
  • 4,5-diarylpyrimidinethiourea compounds and pharmaceutical uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Preparation of compound 1

[0039]In this example, first add 7-isopropoxy isoflavone to the reaction kettle, add methanol 20 times the weight of 7-isopropoxy isoflavone under stirring, then add sodium methoxide and amidinothiourea, the methanol used The amount of sodium is 4 times of the molar weight of the isoflavone compound, the amount of guanidinyl thiourea is 3 times of the molar weight of the isoflavone compound, and the temperature of the reaction solution is 65 ° C with a temperature regulating device, and the reaction is carried out for 3 hours to obtain compound 1 and A mixture of unreacted substances; the reacted mixture was poured into 5 times the amount of 5% hydrochloric acid, statically precipitated, filtered under reduced pressure, washed with distilled water to neutrality, and the crude product Compound 1 was obtained, and the crude product was recrystallized with absolute ethanol to obtain the compound Pure product of 1 (yield 79%).

[0040] The c...

Embodiment 2

[0088] (1) Preparation of compound 1

[0089] In this example, first add 7-isopropoxy isoflavone to the reaction kettle, add methanol 20 times the weight of 7-isopropoxy isoflavone under stirring, then add sodium ethoxide and amidinothiourea, the ethanol used The amount of sodium is 4 times of the molar weight of the isoflavone compound, and the amount of guanidinyl thiourea is 4 times of the molar weight of the isoflavone compound. The temperature of the reaction solution is 65 ° C with a temperature regulating device, and the reaction is carried out for 3 hours to obtain compound 1 and A mixture of unreacted substances; the reacted mixture was poured into 5 times the amount of 5% hydrochloric acid, statically precipitated, filtered under reduced pressure, washed with distilled water to neutrality, and the crude product Compound 1 was obtained, and the crude product was recrystallized with absolute ethanol to obtain the compound Pure product of 1 (73% yield).

[0090] (2) Pr...

Embodiment 3

[0093] (1) Preparation of compound 1

[0094] In this example, first add 7-isopropoxy isoflavone to the reaction kettle, add methanol 20 times the weight of 7-isopropoxy isoflavone under stirring, then add sodium hydroxide and amidinothiourea, the used The amount of sodium hydroxide is 6 times of the molar weight of the isoflavone compound, the amount of amidinyl thiourea is 4 times of the molar weight of the isoflavone compound, and the temperature of the reaction solution is 65 °C with a temperature regulating device, and the reaction is carried out for 4 hours to obtain the compound 1 and unreacted mixture; the reacted mixture was poured into 5 times the amount of 5% hydrochloric acid, static precipitation, filtered under reduced pressure, washed with distilled water until neutral, to obtain the crude compound 1, the crude product was recrystallized with absolute ethanol, The pure product of compound 1 was obtained (yield 71%).

[0095] (2) Preparation of compound 2-15

...

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Abstract

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. The present invention provides a class of 4,5-diarylpyrimidinethiourea compounds conforming to the general formula 1. The process includes: adding reactant isoflavones to a solvent, and then adding a basic catalyst, amidinothiourea, and isoflavones The compound reacts chemically with amidinothiourea to obtain a mixture of the compound of the present invention and unreacted matter, which is purified by suction filtration under reduced pressure and recrystallization or column chromatography to obtain the pure product of the compound of the present invention. Also provided are a class of bactericidal drugs and compositions. Formula 1

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] Pyrimidinethiourea compounds are a class of compounds with a wide range of biological activities. Pyrimidine derivatives are widely used in pesticides, medicines and synthetic intermediates. Pyrimidine derivatives are important components of nucleic acids and biological enzymes. They have anti-tumor, anti-cancer, antibacterial and anti-inflammatory effects, and also have broad-spectrum insecticidal properties. and herbicidal effect. Thioureas are also a hotspot of development at present, mainly used in anti-HIV, anti-cancer, and anti-viral drugs; they also have certain applications in sterilization and pain relief. [0003] Natural isoflavones have broad-spectrum ...

Claims

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Application Information

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IPC IPC(8): A61P31/04A61K31/505C07D239/42
Inventor 张尊听韩文勇李刚薛东刘谦光
Owner SHAANXI NORMAL UNIV
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