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N-substituted phenyl-2-((1H-benzimidazole-2-group) sulfydryl) amides derivatives and usage thereof

A technology of benzimidazole and acetamide, applied in the field of organic compound synthesis and pharmaceutical application, to achieve obvious anti-HIV-1 virus activity, high selectivity index, and small cytotoxic effect

Inactive Publication Date: 2014-11-05
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, problems such as drug toxicity caused by long-term medication, the emergence of HIV multidrug-resistant virus strains, and patient tolerance to drugs have forced people to continuously develop new anti-AIDS drugs and new clinical treatment options, especially high-efficiency, low-toxicity, anti-AIDS, and anti-AIDS. The development of new drugs for drug resistance has always been a research hotspot in the field of international drug research

Method used

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  • N-substituted phenyl-2-((1H-benzimidazole-2-group) sulfydryl) amides derivatives and usage thereof
  • N-substituted phenyl-2-((1H-benzimidazole-2-group) sulfydryl) amides derivatives and usage thereof
  • N-substituted phenyl-2-((1H-benzimidazole-2-group) sulfydryl) amides derivatives and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Intermediate 2-((1 H -Benzimidazol-2-yl)-mercapto)- N -(2-trifluoromethyl) phenyl) acetamide synthesis, concrete operations are as follows:

[0029]

[0030] Add 2-mercapto-1 to a dry three-necked flask H -Benzimidazole (0.02mol), dissolved in 10ml DMF, added anhydrous potassium carbonate solid (0.02mol), gradually heated to 70°C, added 2-bromo- N -(2-(trifluoromethyl)phenyl)acetamide, continue stirring reaction at 70°C, TLC tracking for about 4 hours, reactant 2-bromo- N -(2-(Trifluoromethyl)phenyl)acetamide disappeared. The reaction was stopped, and the reaction solution was poured into ice water to precipitate a precipitate, which was filtered under reduced pressure and dried to obtain a crude product, which could be directly used in the next step without purification.

Embodiment 2

[0031] Example 2 : N -(3-Bromophenyl)-2-((1-cyclohexylcarbonyl)-1 H - the synthesis of benzo [d] imidazol-2-yl) mercapto) acetamide (Ia), the specific operations are as follows:

[0032] Add 2-((1 H -Benzimidazol-2-yl)-mercapto)- N -(3-Bromophenyl)acetamide (0.002mol), dissolved in 5ml of DMF and then added to 0.5ml of triethylamine solution to adjust the pH value to 8. Cyclohexylformyl chloride liquid (0.002mol) was added, and the temperature was gradually raised to 65°C. After TLC followed the reaction for 6 hours, the reactant cyclohexylformyl chloride disappeared. The reaction was stopped, and the reaction solution was poured into ice water to precipitate a precipitate, which was filtered, washed three times with absolute ethanol, and dried by suction to obtain a crude product. After the crude product was subjected to column chromatography (petroleum ether: ethyl acetate = 3:1), a pure white solid Ia was obtained. The test results are as follows:

[0033] the I...

Embodiment 3

[0035] Example 3 : N -(3,5-difluorophenyl)-2-((1-cyclohexylcarbonyl)-1 H - Benzo [d] imidazol-2-yl) mercapto) acetamide (Ib) synthesis, concrete operations are as follows:

[0036] Add 2-((1 H -Benzimidazol-2-yl)-mercapto)- N -(3,5-difluorophenyl)acetamide (0.002mol), dissolved in 5ml of DMF, then added 0.5ml of triethylamine solution, and adjusted the pH value to 8. Cyclohexylformyl chloride liquid (0.002mol) was added, and the temperature was gradually raised to 65°C. After TLC followed the reaction for 6 hours, the reactant cyclohexylformyl chloride disappeared. Stop the reaction, pour the reaction solution into ice water, precipitate the precipitate, filter, wash the product with absolute ethanol 3 times, filter and dry to obtain the crude product. After the crude product is subjected to column chromatography (petroleum ether: ethyl acetate=3:1), a white solid Ib is obtained, and the detection results are as follows:

[0037] Ib

[0038] Yield: 17.4%; Melting p...

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Abstract

The invention discloses N-substituted phenyl-2-((1H-benzimidazole-2-group) sulfydryl) amides derivatives with the following structural general formula, wherein R1 is selected from hydrogen, halogen (F, Cl, Br and I), trifluoromethyl, methoxy, nitro or sulfamine; X is -C (=O)- or -SO2-; and R is cyclohexyl, phenyl or tolyl. The compounds have novel structure framework and better human immunodeficiency virus (HIV)-1 resistance activity, and can be used as lead compounds for preparing the medicine for resisting HIV.

Description

Technical field [0001] The present invention involves one N -Stephenyl-2- ((1 H -Phenylene pyramole-2-base) acetamide derivatives and their preparation methods and applications, which are the fields of organic compound synthesis and pharmaceutical application technology. Background technique [0002] AIDS (AIDS) is an epidemic infectious disease caused by Human ImmunodeFicience (HIV).Seriously endanger human health and social security and stability. [0003] Since the first anti -AIDS drug Zidov in 1987, the US FDA has approved 31 drugs for treating AIDS.They are targeted at different links and targets during HIV replication, including nucleoside and non -nucleoside reverse translotrase inhibitors, protease inhibitors, integrated enzyme inhibitors, fusion inhibitors, and trend factor receptor antagonists.These drugs effectively inhibit the replication of HIV virus in the human body, and play a positive role in reducing the virus load, improving the quality of life of HIV-1 infect...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/28A61K31/4184A61P31/18
Inventor 王月平闫婉露郭琼何严萍
Owner KUNMING UNIV OF SCI & TECH