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Sulfonamide compound and its preparation method and use

A technology of sulfonamides and compounds, applied in the field of medicinal chemistry

Active Publication Date: 2020-12-01
FOSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the high mutation rate of HIV, drug resistance is still a major problem in the treatment of this virus. Therefore, it is still urgent to develop new protease inhibitors to overcome a series of problems of existing HIV-1 protease inhibitors. Therefore, the design and synthesis of new protease inhibitors is currently a hot spot in the field of new AIDS drug research and development.

Method used

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  • Sulfonamide compound and its preparation method and use
  • Sulfonamide compound and its preparation method and use
  • Sulfonamide compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061]A preparation method of a novel sulfonamide compound includes the following steps:

[0062](1) Put 300mg of NaBH4Add to 10mL of ethylene glycol dimethyl ether and stir evenly, then control its temperature at -5°C to obtain liquid A;

[0063](2) Add 1.9 g of methanesulfonic acid to 1 mL of ethylene glycol dimethyl ether and stir evenly to obtain liquid B;

[0064](3) Slowly add liquid B to liquid A and stir evenly, while controlling the temperature at -5°C to obtain mixed liquid C;

[0065](4) Add 1.2 g of compound 6 and 1.4 mL of isopropanol (i-PrOH) to 2.7 mL of ethylene glycol dimethyl ether and stir evenly to obtain D mixture;

[0066](5) Slowly add D mixture to C mixture, and control the temperature at -5℃, stir for 12h, then slowly add 1.2 mL of triethanolamine while keeping the temperature at -5℃, and stir at -5℃ for 30 Minutes later, slowly add 1.8mL NaBH containing 250mg4Dimethylacetamide solution to obtain E mixture;

[0067](6) Stir the E mixture at 0℃ for 2h, then quench with 10mL of...

Embodiment 2

[0072]A preparation method of a novel sulfonamide compound includes the following steps:

[0073](1) Put 300mg of NaBH4Add to 10mL of ethylene glycol dimethyl ether and stir evenly, then control its temperature at -5°C to obtain liquid A;

[0074](2) Add 1.9 g of methanesulfonic acid to 1 mL of ethylene glycol dimethyl ether and stir evenly to obtain liquid B;

[0075](3) Slowly add liquid B to liquid A and stir evenly, while controlling the temperature at -5°C to obtain mixed liquid C;

[0076](4) Add 1.2 g of compound 8 and 1.4 mL of isopropanol (i-PrOH) to 2.7 mL of ethylene glycol dimethyl ether and stir evenly to obtain a D mixture;

[0077](5) Slowly add D mixture to C mixture, and control the temperature at -5℃, stir for 12h, then slowly add 1.2 mL of triethanolamine while keeping the temperature at -5℃, and stir at -5℃ for 30 Minutes later, slowly add 1.8mL NaBH containing 250mg4Dimethylacetamide solution to obtain E mixture;

[0078](6) Stir the E mixture at 0℃ for 2h, then quench with 10mL ...

Embodiment 3

[0083] Same as Example 2, except that the amine group and amido group of compound 22 were deprotected to obtain compound 3.

[0084]Using 15 mg of compound 22 in Example 2 with 9:1 trifluoroacetic acid (TFA): CH2Cl2Treat for 30 minutes, use toluene to co-evaporate to remove the solvent, under the protection of nitrogen, the resulting residue is mixed with N-benzenesulfonylvaline in tetramethylurea tetrafluoroborate, triethylamine and dimethylformamide The solution was reacted at room temperature for 10 hours to obtain compound 3. The LCMS test confirmed that the obtained compound 3 had the stated structure.

[0085]In vitro enzyme assays and intracellular assays were used to determine the inhibitory activities of heterocyclic arylsulfonamide derivatives: compound 3, compound 4, compound 5, compound 23a, compound 23b, and compound 23c on HIV protease. See Table 1. Interestingly, the most effective analog was found to be compound 3 (Ki = 0.6 nM). Replacing the C5 benzyl ring with ethyl does...

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Abstract

The invention discloses a novel sulfamide compound, and a preparation method and application thereof. The preparation method of the novel sulfamide compound comprises the following steps: performing reaction on a compound 6 to generate a compound 9, obtaining a compound 12 by the compound 9, obtaining a compound 15 by the compound 12, obtaining a compound 21 by the compound 15, and obtaining a compound 4 by the compound 21; performing reaction on a compound 8 to generate a compound 11, obtaining a compound 14 by the compound 11, obtaining a compound 17 by the compound 14, obtaining a compound22 by the compound 17, and obtaining a compound 5 by the compound 22. Optionally, the compound 22 is subjected to reaction to generate a compound 3. The novel sulfamide compound can serve as an HIV-1protease inhibitor.

Description

Technical field[0001]The invention belongs to the technical field of medicinal chemistry, and specifically relates to a novel sulfonamide compound and a preparation method and application thereof.Background technique[0002]Because HIV-1 protease plays an important role in the replication of HIV virus, HIV-1 protease is the main target of AIDS drug treatment. Several protease inhibitors such as Lopinavir and Tipranavir have been shown to have effective inhibitory activity against HIV virus. However, due to the high mutation rate of HIV, drug resistance is still the main problem in the treatment of this virus. Therefore, there is still an urgent need to develop new protease inhibitors to overcome a series of problems of existing HIV-1 protease inhibitors. Therefore, the design and synthesis of new protease inhibitors is a hot spot in the research and development of new AIDS drugs.Summary of the invention[0003]Aiming at the problems in the prior art, the present invention provides a nov...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/71C07C311/19C07C303/40A61P31/18C07D409/04C07D261/08C07D231/12
Inventor 丁毅力李紫元王丙云
Owner FOSHAN UNIVERSITY
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