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2,4-dihydroxy-5,6-substituted-1-halogenobenzene derivative, synthesis method and application thereof

A synthetic method, dihydroxy technology, applied in the field of 2,4-dihydroxy-1-halogenated benzene derivatives, to achieve good development and application prospects

Inactive Publication Date: 2013-05-08
TSINGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are many ways to treat and prevent obesity and obesity-induced complications. Except for physical exercise and changes in lifestyle and diet, there is no obvious effective drug to prevent and treat obesity.

Method used

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  • 2,4-dihydroxy-5,6-substituted-1-halogenobenzene derivative, synthesis method and application thereof
  • 2,4-dihydroxy-5,6-substituted-1-halogenobenzene derivative, synthesis method and application thereof
  • 2,4-dihydroxy-5,6-substituted-1-halogenobenzene derivative, synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The first type of compound in the patent of the present invention can be synthesized by the following scheme Synthesis (4) of the key intermediate compound 2,4-dimethoxy-5-chlorophenylboronic acid and the target compound.

[0019]

[0020] Compound (2): When R 3 When =H, add 2,4-dimethoxybenzene and THF into the round bottom flask, add dibromohydantoin (DBDMH) at room temperature, and continue stirring at room temperature for 6h after the addition is complete. TLC monitoring, after the reaction was completed, the solvent was evaporated in vacuo, water was added to the flask, the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, evaporated to dryness to obtain colorless transparent crystal compound (2), the yield was 96% ; 1 H NMR (300 MHz, CDCl 3 ): 7.39 (1H, d, J = 9.0 Hz, Ar-H), 6.47 (1H, s, Ar-H), 6.38 (1H, d, J = 9.0 Hz, Ar-H), 3.85 (3H, s , OCH 3 ), 3.78 (3H, s, OCH 3 ).

[0021] Compound (3): In a round bottom flask, add compo...

Embodiment 2

[0040] The second type of compound in the patent of the present invention can synthesize the key intermediate compound (8) and the target compound by the following scheme.

[0041]

[0042] Compound (2): Add raw materials p-chlorophenol, solid anhydrous potassium carbonate, and acetone into a 500 mL round bottom flask, add methyl iodide, install a reflux condenser, and heat to reflux. TLC followed the reaction, and the reaction was complete. Then the solvent and residual methyl iodide were evaporated under reduced pressure, the obtained solid was extracted with ethyl acetate, the organic phase was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the crude product of light yellow oil was separated and purified by silica gel column to obtain compound (2) as colorless oil with a yield of 98%. 1 H NMR (300 MHz, CD 3 Cl 3 ): δ 3.80 (3H, s), 3.88 (3H, s), 6.43(1H, dd, J = 9 Hz, 3Hz), 6.50 ...

Embodiment 3

[0064] The third type of compound in the patent of the present invention can synthesize the key intermediate compound (2) and the target compound by the following scheme.

[0065]

[0066]

[0067] Compound (2): dissolving m-phenylenedimethyl ether and n-chlorosuccinimide in acetonitrile, the system was heated to reflux for 17 hours, the solvent was evaporated, and the column was passed through petroleum ether to obtain a colorless oily compound (2 ), the yield is 90%. 1 H NMR (300 MHz, CDCl 3 ) δ: 7.26-7.23 (m, 1H), 6.51 (d, 1H, J =2.7Hz), 6.43 (dd, 1H, J =2.7, 8.7Hz), 3.87 (s, 3H), 3.79 (s, 3H ).

[0068]

[0069] Compound (3): Add 1-adamantanol to the mixture of compound (2) and trifluoroacetic acid, stir at room temperature for 0.5 hours, add 15 mL of water to the reaction system, then extract with ethyl acetate, combine organic phase, dried with anhydrous sodium sulfate, evaporated to dryness, and purified by thin-layer chromatography using petroleum ether as a deve...

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Abstract

The invention discloses a 2,4-dihydroxy-5,6-substituted-1-halogenobenzene derivative, a synthesis method and an application thereof, belonging to the field of pharmaceutical chemistry. The 2,4-dihydroxy-5,6-substituted-1-halogenobenzene derivative has the following structural general formula. The compound is of an active ingredient, and when the compound is applied to preparation of medicaments for treating, preventing or relieving complicating diseases and the like caused by obesity, the activity is better.

Description

technical field [0001] The present invention relates to a series of 2,4-dihydroxyl-1-halogenated benzene derivatives substituted at 5-position or 6-position and substituted 5,6-cyclization, their preparation method and the effects of these compounds on treating, preventing or alleviating obesity The application in aspects such as the complications caused by it belongs to the field of medicinal chemistry. Background technique [0002] With the rapid development of the global economy, the changes in diet structure and the reduction of physical labor caused by the improvement of people's living standards, the incidence of obesity is increasing day by day, and it has become the world's most important health problem. According to incomplete statistics, obesity in the world is doubling every five years at an astonishing rate, and the number of cases is roughly 500 million. The number of direct or indirect deaths caused by obesity has reached 300,000 each year, and it may become t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/747C07D313/00C07C39/42C07D311/60C07D311/94C07C49/83C07C49/84C07C205/45C07C233/60C07C69/753C07C45/64C07C37/055C07C201/12C07C231/12A61K31/122A61K31/365A61K31/055A61K31/353A61K31/352A61K31/12A61K31/167A61K31/216A61P3/04
Inventor 柴继杰常俊标韩志富宋传军
Owner TSINGHUA UNIV
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