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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: 2014-12-31
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 against HIV-1 virus but not against HIV-2 virus

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

Embodiment 1

[0025] Example 1 : 5-ethyl-6-cyclohexylmethyl-2-[(4-benzoyloxy)phenylcarbonylmethylthio]pyrimidine-4(3 H )-ketone synthesis, concrete operation is as follows:

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

[0027] 1a

[0028] Yield: 75%: Melting point: 169-170°C; 1 H NMR ((300MHz, CDCl 3 ) δ ppm 0.86-1.26 (m, 8H, C...

Embodiment 2

[0029] Example 2 : 5-ethyl-6-cyclohexylmethyl-2-[(4-cyclohexyloxy)phenylcarbonylmethylthio]pyrimidine-4(3 H )-ketone synthesis, concrete operation is as follows:

[0030] 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), stirred at room temperature for 0.5 hours, added α-chloro-4-cyclohexyloxyacetophenone (3.3 mmol), continued stirring reaction at 80 ° C, TLC traced the disappearance of the raw material point for about 20 hours, stopped For reaction, pour the reaction solution into 50 ml of ice water, stir to precipitate the precipitate, filter, wash the precipitate with water, suction filter and dry at 70°C to obtain the crude product, which is subjected to column chromatography (petroleum ether: ethyl acetate = 2:1) Finally, white crystal 1b was obtained, and the detection results were as follows:

[0031] 1b

[0032] Yield: 62%: Melting point: 154-155°C; 1 H NMR (300MHz, CDCl 3...

Embodiment 3

[0033] Example 3 : 5-ethyl-6-benzyl-2-[(4-benzoyloxy)phenylcarbonylmethylthio]pyrimidine-4(3 H )-ketone synthesis, concrete operation is as follows:

[0034] Dissolve 5-ethyl-6-benzyl-2-thiouracil (3 mmol) in 10 ml of dry N , N -Dimethylformamide solution, add K 2 CO 3 (3 mmol), stirred and reacted at room temperature for 0.5 hours, added α-bromo-4-benzoyloxyacetophenone (3.3 mmol), continued to stir and reacted at 20°C, TLC traced the disappearance of the raw material point for about 8 hours, and stopped the reaction , pour the reaction solution into 50 ml of ice water, stir to precipitate the precipitate, filter, wash the precipitate with water, suction filter and dry at 70°C to obtain the crude product, which is subjected to column chromatography (petroleum ether: ethyl acetate = 2:1) , to obtain white crystal 1c, the detection results are as follows:

[0035] 1c

[0036] Yield: 68%: Melting point: 172.6-173.8°C; 1 H NMR (300MHz, CDCl 3 ) δ ppm 1.04 (t, 3H,...

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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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Patent Type & Authority Patents(China)
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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