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Application of Beta-aminoketones compound in preparing drug for inhibiting isocitrate lyase

A technology of isocitric acid and amino ketone, which is applied in the direction of active ingredients of heterocyclic compounds, drug combinations, antibacterial drugs, etc., can solve the problems of easy relapse, long course of tuberculosis chemotherapy, poor curative effect, etc.

Inactive Publication Date: 2009-12-30
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The latent infection of Mycobacterium tuberculosis (MTB) is one of the main reasons for the long course of tuberculosis chemotherapy, poor efficacy and easy relapse after chemotherapy.

Method used

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  • Application of Beta-aminoketones compound in preparing drug for inhibiting isocitrate lyase
  • Application of Beta-aminoketones compound in preparing drug for inhibiting isocitrate lyase
  • Application of Beta-aminoketones compound in preparing drug for inhibiting isocitrate lyase

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0109] One, the preparation general method of β-amino ketone compound

[0110]

[0111] Dissolve 20mmol of aromatic aldehyde and 20mmol of aromatic amine in 40-60mL of absolute ethanol, add a small amount of inorganic acid or Lewis acid as a catalyst, stir electromagnetically until solids are precipitated, then add 20mmol of aromatic ketone (when the aromatic ketone is nabumetone, Dissolve it in 5-20 mL of chloroform before adding it), adjust the pH to 4-5 with concentrated hydrochloric acid, continue to stir, and monitor with thin-layer chromatography (TLC) until the reaction reaches equilibrium or the reaction is complete. Stand overnight at ℃, filter with suction, wash the filter cake with water and ethanol in turn, drain and recrystallize to obtain β-aminoketone compounds.

Embodiment 1

[0112] Embodiment 1, ydcm01:1, the preparation of 3-bis(4-chlorophenyl)-3-(4-chloroanilino)propan-1-one

[0113]

[0114] Dissolve 2.8g (20mmol) of 4-chlorobenzaldehyde and 2.6g (20mmol) of 4-chloroaniline in 40mL of absolute ethanol, add a small amount of concentrated hydrochloric acid as a catalyst, stir electromagnetically until solids are precipitated, and then add 4-chlorophenylethyl Ketone 3.1g (20mmol), adjust the pH to 4-5 with concentrated hydrochloric acid, continue to stir, monitor with TLC until the reaction reaches equilibrium or the reaction is complete, the reaction solution is allowed to stand overnight at a temperature of 2-8°C, suction filtered, and the filter cake is watered in turn Washed with ethanol, drained, and recrystallized to obtain 6.93 g of the target product with a yield of 86%.

[0115] The structural characterization data of the product are as follows: IR (KBr, cm -1 ): 3407(s, v NH ), 1675 (vs, v C＝O ), 1593 (vs, ), 1499 (vs, ), 815(s...

Embodiment 2

[0116] Example 2, ydcm07: Preparation of 1-(4-chlorophenyl)-3-(3,4-dichlorophenyl)-3-(4-bromoanilino)propan-1-one

[0117]

[0118] Dissolve 3.5g (20mmol) of 3,4-dichlorobenzaldehyde and 3.4g (20mmol) of 4-bromoaniline in 45mL of absolute ethanol, add a small amount of concentrated hydrochloric acid as a catalyst, stir electromagnetically until solids are precipitated, and then add 4- Chloroacetophenone 3.1g (20mmol), adjust the pH to 4-5 with concentrated hydrochloric acid, continue to stir, monitor with TLC until the reaction reaches equilibrium or the reaction is complete, the reaction solution is left standing overnight at a temperature of 2-8°C, suction filtered, filtered The cake was washed with water and ethanol in sequence, drained and recrystallized to obtain 8.08 g of the target product with a yield of 84%.

[0119] The structural characterization data of the product are as follows: IR (KBr, cm -1 ): 3398 (vs, v NH ), 1670 (vs, v C＝O ), 1589 (vs, ), 1501 (vs,...

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Abstract

The invention discloses an application of a Beta-aminoketones compound with the following general formula in preparing a drug for inhibiting isocitrate lyase. The invention adopts a high throughput screening model of isocitrate lyase inhibitor, screens out the Beta-aminoketones compound with isocitrate lyase inhibiting activity from a great number of new synthesized compounds, and preliminarily tests the bioactivity of the Beta-aminoketones compound. According to a test result, the Beta-aminoketones compound has certain isocitrate lyase inhibiting activity and can be developed into a drug which inhibits the isocitrate lyase and is used for preventing or treating diseases caused by a plurality of pathogenic microorganisms such as mycobacterium tuberculosis, candida albicans, rhodococcus equi, etc.

Description

technical field [0001] The invention relates to the medical application of the compound, in particular to the application of the β-aminoketone compound in the preparation of a drug for inhibiting isocitrate lyase. Background technique [0002] The latent infection of Mycobacterium tuberculosis (MTB) is one of the main reasons for the long course of chemotherapy for tuberculosis, poor curative effect and easy relapse after chemotherapy. Isocitrate lyase (ICL) is the most positive factor found so far related to latent infection of Mycobacterium tuberculosis, and it is also one of the virulence factors of Mycobacterium tuberculosis. As a key enzyme of the glyoxylate cycle, isocitrate lyase catalyzes isocitrate to generate glyoxylate and succinate, thereby changing the flow direction of carbon sources, which is conducive to the accumulation of carbon sources, and is used by Mycobacterium tuberculosis in a latent state Fatty acids or acetic acid provide favorable conditions for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/137A61K31/36A61K31/635A61K31/196A61P43/00A61P31/04
Inventor 杨大成谢建平范莉冀磊刘红萍龙泉鑫唐雪梅周祖文张映霞苏小燕
Owner SOUTHWEST UNIV
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