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N-substituted phenyl-2-(1-aryl-1H-imidazolyl-2-sulfhydryl) acetamides derivates, preparation method thereof and application

A technology of acetamide and derivatives, applied in the field of anti-HIV drugs, can solve problems such as metabolic instability in the body

Inactive Publication Date: 2009-02-11
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although triazole and tetrazole thioethanamide compounds have high activity against wild-type and drug-resistant strains, they still have disadvantages such as unstable metabolism in vivo.

Method used

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  • N-substituted phenyl-2-(1-aryl-1H-imidazolyl-2-sulfhydryl) acetamides derivates, preparation method thereof and application
  • N-substituted phenyl-2-(1-aryl-1H-imidazolyl-2-sulfhydryl) acetamides derivates, preparation method thereof and application
  • N-substituted phenyl-2-(1-aryl-1H-imidazolyl-2-sulfhydryl) acetamides derivates, preparation method thereof and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1. Preparation of intermediate 1-(4-chlorophenyl)-1H-imidazole-2-mercapto (3a)

[0032] Dissolve 8.5g (0.05mol) of p-chlorophenylisothiocyanate (1a) in 100ml of EtOH, add 5.3g (0.05mol) of aminoacetaldehyde dimethyl acetal dropwise under stirring at room temperature, and stir for 30min after dropping, the reaction is exothermic , a large amount of white solids were precipitated, the reaction liquid was cooled, suction filtered, washed with cold EtOH, and 1-(4-chlorobenzene)-3-(2,2-dimethoxyethyl)thiourea (2a) crude product was obtained, no purification was necessary , proceed directly to the next reaction. The crude product was heated to reflux with 50ml 5N HCl for 3h, cooled, the reaction solution was adjusted to be alkaline with 4N NaOH solution, filtered with suction, the filtrate was acidified with concentrated hydrochloric acid, a large amount of white solid was precipitated, washed with water, and dried to obtain 1-(4-chlorobenzene )-1H-imidazole-2-mer...

Embodiment 2

[0033] Example 2. Preparation of N-(2-chlorophenyl)-2-(1-(4-chlorophenyl)-1H-imidazole-2-mercapto)acetamide (5a1)

[0034] Add 0.08g (0.002mol) NaOH to the suspension of 0.42g (0.002mol) 1-(4-chlorobenzene)-1H-imidazole-2-mercapto (3a) in EtOH (30ml), stir at room temperature, and wait until the suspension After the liquid is clarified, add 0.40 g of equivalent 2-chloroacetyl-N-o-chloroaniline (4.1), continue to stir at room temperature, TLC detects that the reaction is complete, and evaporate the solvent to dryness under reduced pressure to obtain an off-white solid, to which 30 ml of dichloromethane is added , washed with 3×30ml water, the organic layer was dried, concentrated, and recrystallized from EtOH to obtain 0.37g of the target compound (5a1), white needle-like crystals, yield: 48.9%, mp: 233.1-235.0°C.

[0035] Product spectral analysis data:

[0036] 1 H-NMR (CDCl 3 , ppm) δ: 10.54 (s, 1H, NH), 8.33 (d, 1H, J=7.8Hz), 7.46 (d, 2H, J=8.4Hz, PhH), 7.35 (dd, 1H, J ...

Embodiment 3

[0040] Example 3. Preparation of N-(2-nitrophenyl)-2-(1-(4-chlorophenyl)-1H-imidazole-2-mercapto)acetamide (5a2)

[0041] Method as described in Example 2, the difference is to add 0.10g (0.001mol) Na to the EtOH (30ml) suspension of intermediate reagent 3a0.42g (0.002mol) prepared in Example 1 2 CO 3 , stirred at room temperature, and after the suspension was clarified, 0.43 g of an equivalent amount of 2-chloroacetyl-N-o-nitroaniline (4.2) was added, and continued to stir at room temperature. TLC detected that the reaction was complete, and the solvent was evaporated to dryness under reduced pressure to obtain a yellow solid , adding 30ml of dichloromethane to it, washing with 3×30ml of water, drying the organic layer, concentrating, and recrystallizing with EtOH to obtain 0.30g of the target compound (5a2), light yellow needle-like crystals, yield: 38.7%, mp: 240.1-241.8°C .

[0042] Product spectral analysis data:

[0043] IR (KBr, cm -1 )3156(υ NH ), 1708 (υ -CONH- ...

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Abstract

The invention provides an N-substituted phenyl-2(1-aryl-1H-imidazole-2-mercapto-) acetyl amine derivative and the structural general formula is shown as the formula on the right; wherein, Ar is p-chlorophenyl or 1-naphthyl; X is F, Cl, Br, NO2 or CH3; and Y is H or CH3. The derivative has novel structural framework and relatively high activity in inhibiting HIV and can be used as a lead compound for preparing anti-HIV drugs.

Description

technical field [0001] The invention relates to N-substituted phenyl-2-(1-aryl-1H-imidazole-2-mercapto)acetamide derivatives, a preparation method and an application as an HIV-1 non-nucleoside inhibitor, belonging to anti-HIV drugs technology field. Background technique [0002] Human immunodeficiency virus type 1 (HIV-1) is the main pathogen of AIDS (AIDS). Since its discovery in 1981, AIDS has become a major infectious disease that endangers human life and health. Although the implementation of HAART is a major breakthrough in anti-AIDS treatment, the emergence of drug resistance and the toxicity of long-term medication have greatly limited the application of this therapy, and the development of new anti-AIDS drugs is urgent. Reverse transcriptase plays a key role in the entire life cycle of the virus, non-nucleoside inhibitors (NNRTIs) targeting the non-substrate binding site of HIV-1RT have the advantages of high efficiency and low toxicity, and become an important par...

Claims

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Application Information

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IPC IPC(8): C07D233/84A61K31/4164A61P31/18
Inventor 刘新泳展鹏
Owner SHANDONG UNIV
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