Diaryl pyrimidone hydrazone derivatives and preparation method and application of diaryl pyrimidone hydrazone derivatives

A technology of diarylpyrimidinone hydrazones and derivatives, which is applied in the field of medicine to achieve the effect of novel structure, low cytotoxicity and good anti-HIV biological activity

Inactive Publication Date: 2011-08-17
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Classical NNRTIs are only effective ag...

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  • Diaryl pyrimidone hydrazone derivatives and preparation method and application of diaryl pyrimidone hydrazone derivatives
  • Diaryl pyrimidone hydrazone derivatives and preparation method and application of diaryl pyrimidone hydrazone derivatives
  • Diaryl pyrimidone hydrazone derivatives and preparation method and application of diaryl pyrimidone hydrazone derivatives

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Experimental program
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Embodiment 1

[0039] Embodiment 1: the synthesis of diaryl pyrimidinone hydrazone derivatives

[0040] Put the hydrazine derivatives and different substituted pyrimidinone derivatives II in the solvent, and then raise the temperature (alkali should be added for the hydrazine salt), after the reaction is completed, pour the reaction solution into ice water, extract with ethyl acetate, and distill The ester was washed once with 2 M hydrochloric acid and once with saturated brine, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain the target product. The following examples describe the preparation process method in detail with different examples:

[0041] Substituted pyrimidinone derivative II (6 mmol) and hydrazine dihydrochloride (3.15 g, 30 mmol) were dissolved in EtOH (30 mL), then pyridine (6.5 mL g, 80 mmol) was added, and then the temperature was raised to reflux for 2 h. After the reaction is complete, cool down, pour the reaction solution into water...

Embodiment 2

[0051] Example 2 Anti-HIV biological activity test

[0052] The anti-HIV virus activity at the cell level in vitro was determined by the Rega Institute of Pharmacy at Katholleke University in Belgium, mainly including two aspects: inhibitory activity and cytotoxicity to HIV-infected MT-4 cells. The method is described as follows: make the compound in HIV-infected MT-4 cells, at different times of HIV infection, use the MTT method to measure the protective effect of the drug on the cytopathic changes induced by HIV, and calculate that 50% of the cells are free from HIV-induced cell changes. half effective concentration IC 50 , Toxicity assay was carried out in parallel with anti-HIV activity experiment, and also in MT-4 cell culture, the concentration that caused 50% of uninfected cells to undergo cytopathic changes was determined by MTT method (CC 50 ), and calculate the selectivity index SI=CC 50 / IC 50 .

[0053] Materials and Methods:

[0054] The anti-HIV activity of ...

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Abstract

The invention belongs to the technical field of medicines, particularly relates to diaryl pyrimidone hydrazone derivatives and a preparation method and application of the diaryl pyrimidone hydrazone derivatives. The diaryl pyrimidone hydrazone derivatives also contain medicine salt, a stereochemical isomer, hydrate, solvate, polycrystals or eutectic crystals and a precursor and derivatives with the same biological functions. The preparation method comprises a step that hydrazonium salt and substituted hydrazonium salt react with diaryl pyrimidine in an organic solvent under the action of alkali to prepare target products, or hydrazine, a complex compound of hydrazine and a complex compound of substituted hydrazine directly react with diaryl pyrimidine to prepare the target products. A pharmacological test result shows that most of the compounds have strong inhibitory activity for replication of a wild-type HIV-1 strains and various drug resistant HIV-1 virus strains; part of the compounds have strong inhibitory activity for HIV-2; and the compounds are expected to become HIV-resistant candidate drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a diaryl pyrimidinone hydrazone derivative and its preparation method and application. Background technique [0002] AIDS (AIDS) caused by Human Immunodeficiency Virus (HIV) is one of the persistent diseases that are difficult to overcome in the scientific community. It is showing an outbreak trend and posing an increasingly serious threat to the survival and development of human beings. The existing drugs have certain curative effects, but also have problems such as poor drug resistance and large toxic and side effects. Therefore, searching for anti-AIDS drugs with high efficiency and low toxicity is still a major issue facing medicinal chemists. At present, the research and development of anti-AIDS drugs is mainly based on the understanding of the life cycle of HIV. Among them, reverse transcriptase (RT) plays an important role in the reverse transcription process ...

Claims

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Application Information

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IPC IPC(8): C07D239/42C07C59/255C07C59/265C07C57/15C07C59/245C07C51/41A61K31/505A61P31/18A61P35/00
Inventor 陈芬儿马晓东古双喜
Owner FUDAN UNIV
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