A tetrahydropyridopyrimidine compound and its preparation method and application

A technology of tetrahydropyridine and compound, applied in the field of compound and preparation thereof, can solve problems such as limited synthesis method, and achieve the effects of high atom economy, simple operation and green raw material

Active Publication Date: 2021-06-25
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this strategy requires the pre-preparation of pyridopyrimidines, and the related synthetic methods are very limited

Method used

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  • A tetrahydropyridopyrimidine compound and its preparation method and application
  • A tetrahydropyridopyrimidine compound and its preparation method and application
  • A tetrahydropyridopyrimidine compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] The tetrahydropyridopyrimidine compound described in this example is 2-phenyl-tetrahydropyridopyrimidine (compound shown in formula 3a), and the preparation method includes the following steps: in the reactor, add 1.0 mmol o-aminopyridinemethanol and 0.5 mmol of benzamidine, add 1% triruthenium dodecacarbonyl of the amount of ortho-aminopyridinemethanol substance, then add cesium carbonate of 50% of the amount of ortho-aminopyridinemethanol substance, add 1.5ml of methanol and 1.5ml of t- Pentanol, under nitrogen atmosphere, stirred and reacted at 70°C for 24 hours, cooled to room temperature after the reaction, diluted the reaction solution, filtered, and evaporated under reduced pressure to remove the solvent to obtain the crude product, which was purified by column chromatography The compound represented by formula 3a (yield 81%), the product was in the form of yellow oil.

[0042]

[0043] Compound hydrogen spectrogram and carbon spectrogram shown in formula 3a a...

Embodiment 2

[0051] The tetrahydropyridopyrimidine compound described in this example is 2-(4-methyl-phenyl)-tetrahydropyridopyrimidine (compound shown in formula 3b), and the preparation method comprises the following steps: in the reactor , add 0.5 mmol o-aminopyridinemethanol and 1.0 mmol p-toluidine, add 3% cyclopentadienyl bis(triphenylphosphine) ruthenium(II) chloride to the amount of o-aminopyridinemethanol , then add 100% potassium tert-butoxide in the amount of o-aminopyridinemethanol, add 1.5ml isopropanol and 1.5ml tert-amyl alcohol, stir and react at 150°C for 8 hours, cool to room temperature after the reaction, and dilute the reaction solution , filtered, and the solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, which was purified by column chromatography to obtain the compound shown in formula 3b (80% yield), which was in the form of yellow oil.

[0052]

[0053] The hydrogen spectrogram and the carbon spectrogram of the compoun...

Embodiment 3

[0061] The tetrahydropyridopyrimidine compound described in this example is 2-(4-chloro-phenyl)-tetrahydropyridopyrimidine (compound shown in formula 3c), and the preparation method includes the following steps: in the reactor, add 1.0 Millimoles of ortho-aminopyridinemethanol and 1.0 mmoles of 4-chloro-benzamidine, 3% dichloro(pentamethylcyclopentadienyl)iridium(III) dimer was added to the amount of ortho-aminopyridinemethanol substance (Catalyst, Cat.), add the potassium hydroxide of 50% of the amount of o-aminopyridinemethanol again, add 1.5ml ethanol and 1.5ml tert-amyl alcohol, under nitrogen atmosphere, stir reaction at 120 ℃ for 12 hours, react After cooling to room temperature, the reaction solution was diluted, filtered, and the solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, which was purified by column chromatography to obtain the compound represented by formula 3c (yield 78%).

[0062]

[0063] The hydrogen spectrogr...

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Abstract

The invention discloses a tetrahydropyridopyrimidine compound. The tetrahydropyridopyrimidine compounds of the present invention have a good inhibitory effect on the tested human cancer K562, HL-60, HeLa, BGC-823 cells, and these compounds are used as anti-tumor agents for in vitro anti-tumor activity screening , can also be used in drugs for the prevention and treatment of tumors. The invention also discloses the preparation method of the tetrahydropyridopyrimidines, the preparation method of the invention can realize the tetrahydropyridopyrimidines in moderate to good yields from the o-aminopyridinemethanol substrate and different amidine salts The synthesis of compounds, the products can be widely used in the fields of biomedicine and functional materials. The reaction does not require additional oxidant and inert gas protection, the raw materials are green and cheap, the operation is simple, and it has high atom economy. The invention also discloses the application of the tetrahydropyridopyrimidine compound in the preparation of anti-tumor agents or anti-tumor drugs.

Description

technical field [0001] The invention relates to a compound and its preparation method and application, in particular to a tetrahydropyridopyrimidine compound and its preparation method and application. Background technique [0002] Tetrahydropyridopyrimidine is the core structural unit of a large number of alkaloids and functional molecules, exhibiting very good biological and pharmaceutical activities, such as the compounds shown in the following formulas (1)-(3). [0003] [0004] Generally speaking, the current synthesis method is to hydrogenate quinazoline under high-pressure hydrogen to obtain our target hydrogenated product, as shown in the following formula: [0005] [0006] The synthesis of such compounds can be achieved by high-pressure hydrogenation of pyridopyrimidines. However, this strategy requires the pre-preparation of pyridopyrimidines, and the related synthetic methods are very limited. Therefore, how to directly and effectively synthesize such sem...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/519A61P35/00
CPCA61P35/00C07D471/04
Inventor 陈修文何芊林梁婉仪钟明利陈世杰李亦彪朱忠智
Owner WUYI UNIV
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