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Diaryl ether derivatives as well as preparation method and application thereof

A kind of derivative, the technology of diaryl ether, applied in the application of related medicines, diaryl ether derivatives and the field of preparation thereof, to achieve the effects of small cytotoxicity, enhanced binding force, and strong anti-HIV-1 virus activity

Inactive Publication Date: 2015-09-02
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Classic NNRTIs only work on HIV-1, but not HIV-2, study shows

Method used

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  • Diaryl ether derivatives as well as preparation method and application thereof
  • Diaryl ether derivatives as well as preparation method and application thereof
  • Diaryl ether derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: the synthesis of final product I

[0025] At 20~40℃, add thioether II into the solvent, stir to dissolve, then add oxidant, and stir for 5-10h. TLC showed the reaction was complete. It was washed successively with saturated sodium sulfite solution, saturated sodium carbonate solution, water and saturated brine, and the organic phase was dried over anhydrous sodium sulfate overnight. Filtration, concentration, and recrystallization from toluene gave the desired solid.

[0026] The target compounds were prepared by the above method with different thioethers II, and some results are as follows:

[0027] At room temperature, add 2-{[4-(4-cyano-2,6-dimethylphenol)pyrimidin-2-yl]thio}acetanilide (5.53 mmol) into 60 mL of dichloromethane, stir Dissolved, then added m-chloroperoxybenzoic acid (12.16 mmol), stirred for 9h. TLC showed the reaction was complete. Wash with saturated sodium sulfite solution (20 mL × 2), saturated sodium carbonate solution (20 mL ×...

Embodiment 2

[0066] Embodiment 2: anti-HIV biological activity test

[0067] 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: inhibitory activity and cytotoxicity to HIV-infected MT-4 cells. The method is 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 HIV-induced cytopathy, and calculate that 50% of the cells are free from HIV-induced cytopathy half effective concentration EC 50 , the toxicity assay was carried out in parallel with the anti-HIV activity experiment, 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 / EC 50 .

[0068] Materials and Methods:

[0069] The anti-HIV activity of each compound is monitored by th...

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Abstract

The invention belongs to the technical field of medicine and particularly relates to diary ether derivatives having a general formula I, pharmaceutical salts, hydrates and solvates of the diary ether derivatives, polycrystal or eutectic crystal of the diary ether derivatives, precursors and derivatives having the same biological functions, a preparation method of the diary ether derivatives and application of compositions containing one or more of the compounds in preparation of related medicines for treating Aids. Pharmacological experiment results show that the compounds have remarkable activity of resisting HIV-1 virus, are capable of effectively inhibiting replication of MT-4 cell infected with HIV-1 virus and have relatively low cytotoxicity. The general formula I is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a diaryl ether derivative, a preparation method thereof, and an application in treating AIDS and other related medicines. Background technique [0002] AIDS (Acquired immune deficiency syndrome) is an epidemic infectious disease caused by human immunodeficiency virus (Human immunodeficiency virus, HIV). [0003] Reverse transcriptase (Reverse transcriptase, RT) plays a decisive role in the process of HIV reverse transcription from mRNA to DNA, so it has become one of the important targets for anti-AIDS drug design. [0004] In the existing anti-HIV drug research, non-nucleoside reverse transcriptase inhibitors (NNRTIs) have become one of the hotspots of medicinal chemists in various countries because of their high efficiency and low toxicity. Currently, there are five anti-HIV reverse transcriptase inhibitors approved by the US FDA: Nevirapine, Delavirdine, Efavirenz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/56A61P31/18
CPCC07D239/56
Inventor 陈芬儿万正勇
Owner FUDAN UNIV
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