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3-carbonyl-6-ethoxycarbonyl-thiazole pyrimidine compound and synthesis method and application thereof

An ethoxyformyl and thiazolo technology is applied in the fields of 3-carbonyl-6-ethoxyformyl-thiazolopyrimidine compounds and synthesis, can solve the problems such as few reports on synthesis, and achieves concise preparation method, novel structure, Effects that are easy to implement

Inactive Publication Date: 2009-12-30
NANJING UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN1875955A has found some drug molecular structures can inhibit the formation of staphylococcal biofilm through computer-aided drug design, but there are few reports on the synthesis of these molecules

Method used

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  • 3-carbonyl-6-ethoxycarbonyl-thiazole pyrimidine compound and synthesis method and application thereof
  • 3-carbonyl-6-ethoxycarbonyl-thiazole pyrimidine compound and synthesis method and application thereof
  • 3-carbonyl-6-ethoxycarbonyl-thiazole pyrimidine compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: Synthetic steps and structural confirmation of intermediate (1)

[0039]

[0040] Step 1: Mix 2.88g of ethyl benzoyl acetate, 1.36g of thiourea, 2.04g of p-methoxybenzaldehyde, 675mg of stannous chloride, and 15ml of absolute ethanol, and stir and reflux for 8h. Cool to room temperature, add 200ml of ice water, stir until a white solid precipitates, filter, and recrystallize with absolute ethanol to obtain 4g (yield 72%).

[0041] Step 2: 736mg of the product of step 1, 189mg of chloroacetic acid, 164mg of sodium acetate, 12ml of acetic acid and acetic anhydride (volume ratio 3:1) were stirred and refluxed for 7h. Cool to 25° C., add 200 ml of ice water until a yellow solid precipitates, filter, and recrystallize with methanol to obtain 740 mg (90% yield) of intermediate (1).

[0042] 1 H-NMR (CDCl 3 )δ6.85~7.43(m, 9H), 3.73~3.92(m, 7H), 0.84(t, 3H).

Embodiment 2

[0043] Embodiment 2: Synthetic steps and structural confirmation of intermediate (2)

[0044]

[0045]Step 1: Mix 2.88g of ethyl benzoyl acetate, 1.36g of thiourea, 2.25g of piperonal, 675mg of stannous chloride, and 15ml of absolute ethanol, and stir to reflux for 6h. Cool to room temperature, add 250ml of ice water, stir until a white solid precipitates, filter, and recrystallize with absolute ethanol to obtain 3.6g (yield: 65%).

[0046] Step 2: 764mg of the product of step 1, 189mg of chloroacetic acid, 164mg of sodium acetate, 12ml of acetic acid and acetic anhydride (volume ratio 1:1) were stirred and refluxed for 9h. After cooling to room temperature, 200 ml of ice water was added to precipitate a yellow solid, which was filtered and recrystallized from methanol to obtain 700 mg (85% yield) of intermediate (2).

[0047] 1 H-NMR (CDCl 3 )δ6.10~7.44(m, 8H), 5.95(s, 2H), 3.75~3.92(m, 4H), 0.86(t, 3H).

Embodiment 3

[0048] Example 3: Synthesis steps and structural confirmation of 3-(2-(5-methoxyfuryl)) benzoate

[0049] Step 1: Add 2.05g of anthranilic acid to 24ml of water and 8ml of concentrated hydrochloric acid, add 7ml of sodium nitrite aqueous solution (0.18g / ml) to it, and stir at 0°C for 0.5h. Add 10ml of furfural in acetone (0.14g / ml) and 5ml of copper chloride aqueous solution (0.17g / ml), stir at room temperature for 24h, filter with suction, wash with hot water, and dry to obtain 2.4g of yellow solid (yield 73 %).

[0050] Step 2: 1g of the product of step 1, add 10ml of methanol and a catalytic amount of concentrated sulfuric acid, stir and reflux for 4h, stop the reaction, extract with ethyl acetate, flash column chromatography (ethyl acetate:petroleum ether=1:4) to obtain 250mg of viscous Liquid (25% yield).

[0051] 1 H-NMR (CDCl 3 )δ9.55(s, H), 6.80~8.30(m, 6H), 3.84(s, 3H).

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Abstract

The invention relates to a 3-carbonyl-6-ethoxycarbonyl-thiazole pyrimidine compound and a synthesis method and application thereof. The compound has a right structure formula. The 3-carbonyl-6-ethoxycarbonyl-thiazole pyrimidine compound serving as an inhibiting agent of YyCG histidine kinase protein for a staphylococcus epidermidis signal transduction system has a novel structure, and the adopted method for preparing the compound is simple and easy to implement. The test results of the minimal inhibitory concentration (MIC) and the minimal bactericidal concentration (MBC) show that the compound has excellent inhibitory action on the formation of a staphylococcal biological film and can effectively kill and wound the bacteria in the staphylococcal biological film.

Description

technical field [0001] The present invention relates to a class of 3-carbonyl-6-ethoxyformyl-thiazolopyrimidine compound, its synthesis method and application. In particular, the invention relates to a class of 3-carbonyl-6-ethoxyformyl-thiazolopyrimidine compound, a synthesis method and application thereof, which are inhibitors of the YycG histidine kinase protein of the Staphylococcus epidermidis signal transduction system. Background technique [0002] Staphylococcus is an important pathogen that causes bacterial infection, and it is at the forefront of various bacterial infections. Staphylococcus will stubbornly stay on the surface of medical indwelling objects to form bacterial biofilm. Not only can it resist the immune killing of the host, but it can also prevent traditional antibiotics from penetrating and acting on bacteria to exert a bactericidal effect. Its drug resistance can be as high as 1,000 times that of planktonic bacteria, and it is easy to cause chronic ...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61K31/519A61P31/04
Inventor 韩世清瞿涤潘斌朱明莉吴旸黄仁政
Owner NANJING UNIV OF TECH
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