2-(4-alkylformyloxyphenylcarbonylmethylthio)pyrimidine compounds and application thereof

A technology of hydrocarbyl formyloxybenzene and carbonylmethylthio, which is applied in the field of 2-pyrimidinone compounds to achieve good anti-HIV-1 virus activity, small cytotoxicity, and high selectivity index

Inactive Publication Date: 2012-07-11
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Classical NNRTIs are only effective again

Method used

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  • 2-(4-alkylformyloxyphenylcarbonylmethylthio)pyrimidine compounds and application thereof
  • 2-(4-alkylformyloxyphenylcarbonylmethylthio)pyrimidine compounds and application thereof
  • 2-(4-alkylformyloxyphenylcarbonylmethylthio)pyrimidine compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0025] Example 1 : 5-Ethyl-6-cyclohexylmethyl-2-[(4-benzoyloxy)phenylcarbonylmethylthio]pyrimidine-4(3 H )-The synthesis of ketone, the specific operation is as follows:

[0026] Dissolve 3mmol of 5-ethyl-6-(cyclohexylmethyl)-2-thiouracil in 10 ml of dry N,N -Dimethylformamide solution, add K 2 CO 3 (3 mmol), the reaction was stirred at room temperature for 0.5 hours, α-bromo-4-benzoyloxyacetophenone (3.3 mmol) was added, and the reaction was continued to stir at 40°C. The raw material point disappeared after tracking by TLC for about 18 hours, and the reaction was stopped , Pour the reaction solution into 50 ml ice water, stir to separate out the precipitate, filter, wash the precipitate with water, filter by suction and dry at 70°C to obtain a crude product. The crude product is subjected to column chromatography (petroleum ether: ethyl acetate = 2:1) , White crystal 1a is obtained, the test results are as follows:

[0027] 1a

[0028] Yield: 75%: Melting point: 169-170°C; 1 H ...

Example Embodiment

[0030] Example 2 : 5-Ethyl-6-cyclohexylmethyl-2-[(4-cyclohexanoyloxy)phenylcarbonylmethylthio]pyrimidine-4(3 H )-The synthesis of ketone, the specific operation is as follows:

[0031] Dissolve 5-ethyl-6-(cyclohexylmethyl)-2-thiouracil (3 mmol) in 10 ml of dry N , N -Dimethylformamide solution, add K 2 CO 3 (3 mmol), the reaction was stirred at room temperature for 0.5 hours, α-chloro-4-cyclohexanoyloxyacetophenone (3.3 mmol) was added, and the reaction was continued to stir at 80°C. TLC tracked the disappearance of the raw material for about 20 hours and stopped. To react, pour the reaction solution into 50 ml ice water, stir to precipitate the precipitate, filter, wash the precipitate with water, filter by suction and dry at 70°C to obtain a crude product. The crude product is subjected to column chromatography (petroleum ether: ethyl acetate = 2:1) Later, white crystals 1b were obtained, and the test results are as follows:

[0032] 1b

[0033] Yield: 62%: Melting point: 154-1...

Example Embodiment

[0035] Example 3 : 5-Ethyl-6-benzyl-2-[(4-benzoyloxy)phenylcarbonylmethylthio]pyrimidine-4(3 H )-The synthesis of ketone, the specific operation is as follows:

[0036] Dissolve 5-ethyl-6-benzyl-2-thiouracil (3 mmol) in 10 ml dry N , N -Dimethylformamide solution, add K 2 CO 3 (3 mmol), stir for 0.5 hour at room temperature, add α-bromo-4-benzoyloxyacetophenone (3.3 mmol), continue to stir the reaction at 20°C, TLC tracked for about 8 hours, the raw material point disappeared, stop the reaction , Pour the reaction solution into 50 ml of ice water, stir to precipitate the precipitate, filter, wash the precipitate with water, filter by suction and dry at 70°C to obtain a crude product. The crude product is subjected to column chromatography (petroleum ether: ethyl acetate = 2:1) , White crystal 1c is obtained, the test results are as follows:

[0037] 1c

[0038] Yield: 68%: Melting point: 172.6-173.8°C; 1 H NMR (300MHz, CDCl 3 ) δ ppm 1.04 (t, 3H, J =7.2Hz, CH 2 C H 3 ), 2.56 (q...

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Abstract

The invention discloses 2-(4-alkylformyloxyphenylcarbonylmethylthio)pyrimidine compounds shown as a general formula I, pharmaceutically acceptable salts or N-oxides thereof, or N-oxides of the salts, or pharmaceutically acceptable prodrugs of the compounds. The compounds have high activity of resisting HIV-1 virus, low toxicity and high selectivity index and can be applied to preparing related medicines for treating and preventing Aids.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a class of 2-(4-hydrocarbylformyloxyphenylcarbonylmethylthio)pyrimidinone compounds, which have good anti-HIV-1 virus activity and low toxicity , high selectivity index, can be used in the treatment of AIDS and other related drugs. Background technique [0002] AIDS (Acquired Immune Deficiency Syndrome) is an epidemic infectious disease caused by 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 the design of anti-AIDS drugs. [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 four anti-HIV ...

Claims

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Application Information

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IPC IPC(8): C07D239/56A61K31/513A61P31/18
Inventor 王月平何严萍刘小蜂姚赟
Owner KUNMING UNIV OF SCI & TECH
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