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2-[(substituted phenylamino)carbonyl methylthio]-6-cyclohexylmethyl-3H-pyrimidine-4-ketone compounds, synthetic method thereof and purpose thereof

A technology of carbonylmethylthio and ketone compounds, applied in organic chemistry, antiviral agents, etc., can solve problems such as drug resistance mutations, toxic side effects, and high prices

Inactive Publication Date: 2013-06-19
YUNNAN UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, factors such as drug-resistant mutations, toxic side effects, and high prices caused by long-term medication have prompted scientists from various countries to continuously explore new targets, new drugs, and new treatment options for the treatment of AIDS in order to develop more effective treatments.

Method used

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  • 2-[(substituted phenylamino)carbonyl methylthio]-6-cyclohexylmethyl-3H-pyrimidine-4-ketone compounds, synthetic method thereof and purpose thereof
  • 2-[(substituted phenylamino)carbonyl methylthio]-6-cyclohexylmethyl-3H-pyrimidine-4-ketone compounds, synthetic method thereof and purpose thereof
  • 2-[(substituted phenylamino)carbonyl methylthio]-6-cyclohexylmethyl-3H-pyrimidine-4-ketone compounds, synthetic method thereof and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment one. The general operation of the preparation reaction of 2-[(substituted phenylamino)carbonylmethylthio]-6-cyclohexylmethyl-3H-pyrimidin-4-one (1) is as follows:

[0024] 6-cyclohexylmethyl-2-mercapto-5-alkyl-3H-pyrimidin-4-one (2) (3mmol) and K 2 CO 3 (3.3mmol) in a dry three-necked flask, add 10ml of anhydrous pyridine, stir at room temperature for 30min, add various substituted bromoacetanilides (3.3mmol), stir at room temperature, TLC tracking until the raw material point disappears, stop reaction, pour the reaction solution into ice water and stir to precipitate precipitates, filter, wash with cold water, and dry to obtain white 5-alkyl-6-(cyclohexylmethyl)-2-(substituted phenylaminocarbonylmethylsulfanyl) The crude product of the target compound can be purified by column chromatography or recrystallized with an appropriate solvent to obtain the pure product of the target compound.

[0025] Using different 6-cyclohexylmethyl-2-mercapto-5-alkyl-3-H-py...

Embodiment 2

[0032] Embodiment two. Anti-HIV activity test in vitro

[0033] The compounds of the present invention are screened for HIV reverse transcriptase activity through the Academy of Military Medical Sciences of the Chinese People's Liberation Army and the AIDS Testing Center of the Chinese People's Liberation Army. The specific experimental methods and results are as follows:

[0034] Cells and Viruses:

[0035] MT-2 cells were cultured in RPMI1640 medium (containing 10% fetal bovine serum) for subcultured human T lymphocytes, and subcultured once every 3-4 days. One day before the start of the experiment, 1:2 passage was performed to ensure the state of the cells.

[0036] TZM b1 cells were cultured in DMEM medium (containing 10% fetal bovine serum), subcultured at 1:3, twice a week. HIV-1 ⅢB strain, HIV-1B subtype strain adapted to long-term passage in the laboratory

[0037] experimental method:

[0038] 1. Cell Culture

[0039] One day before the start of the experiment,...

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Abstract

The invention which relates to 2-[(substituted phenylamino)carbonyl methylthio]-6-cyclohexylmethyl-3H-pyrimidine-4-ketone compounds, a synthetic method thereof and a purpose thereof belongs to the technical field of medicaments. The general structure of the compounds is shown in the specification. In the general structure, R is C1-3 alkyl, and R' is C1-3 alkyl, C1-3 alkyloxy, halogen (F, Cl, Br),OH, or SO2NH2 substituting hydrogen at one or more positions of a benzene ring. The compounds which have an anti-HIV activity and a low cytotoxicity can be used as candidates of anti-AIDS medicaments, or can be used as active components of pharmaceutical compositions for anti-HIV in different dosage forms.

Description

technical field [0001] The invention belongs to the technical field of medicines, and specifically relates to 2-[(substituted phenylamino)carbonylmethylthio]-6-cyclohexylmethyl-3H-pyrimidin-4-one compounds, their synthesis method and application. Background technique [0002] It is well known that AIDS is harmful to human health and life, and the development of anti-HIV drugs has undoubtedly become the frontier of today's science. Most of the 33 anti-HIV drugs in clinical use are based on the protein of the virus itself as the target, mainly including: reverse transcriptase (RT) inhibitors that inhibit the reverse transcription of viral RNA and inhibitors that inhibit the assembly, maturation, and release of the virus in host cells Protease inhibitors, integrase inhibitors and fusion inhibitors, etc. Since 1996, high-efficiency antiretroviral therapy (ie, HAART therapy) consisting of reverse transcriptase inhibitors and protease inhibitors has shown a strong antiviral effec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/56A61K31/513A61P31/18
Inventor 何严萍庄道民蔡青青李敬云李聪王华
Owner YUNNAN UNIV
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