Anti-obesity compound and preparing method and application thereof

A compound and obesity technology, applied in organic chemistry, drug combination, metabolic diseases, etc., can solve the problems of high toxicity and poor safety, and achieve the effect of low toxicity, short reaction time and good lipid-lowering activity

Active Publication Date: 2018-02-23
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to overcome the defects of poor safety and high toxicity of existing anti-obesity drugs, and provide an anti-obesity compound

Method used

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  • Anti-obesity compound and preparing method and application thereof
  • Anti-obesity compound and preparing method and application thereof
  • Anti-obesity compound and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: AOCN1

[0060] 5-Methoxyindole-2-carboxylic acid (0.96g, 5mmol) was dissolved in a round bottom flask containing 10mL of dehydrated dichloromethane, and oxalyl chloride (1.27mL, 15mmol) and 2 Drop N,N-dimethylformamide as a catalyst. After 2 hours of reaction, it turns from beige turbidity to dark yellow clarity. After spinning the solvent, it is dissolved in tert-butanol, and 0.68g of anthranilamide is added, and it immediately turns yellow turbidity. , followed by adding potassium tert-butoxide (1.12g, 10mmol), the solution gradually turned orange-red turbid, the temperature was slowly raised from 25°C to 100°C for about 8 hours, and the reaction was stopped. After the reaction solution was cooled to room temperature, it was filtered The filtrate was obtained, and the filtrate was poured into ice water, and a large amount of solids were precipitated by ultrasonication. The pH was adjusted to about 8 with dilute hydrochloric acid, and 1.02 g of a yellow soli...

Embodiment 2

[0066] Example 2: IQN4

[0067] Add 14.4g of anthranilamide into tert-butanol dissolved with 2-indole chloride at room temperature, at this time, the reaction solution turns from brown clear to light yellow turbid; then add 2.4 equivalents of potassium tert-butoxide , the temperature was slowly raised from room temperature to 80°C, and reacted for 9 hours, and the reaction solution turned reddish brown and turbid. Stop the reaction, cool and let it stand, pour into a large amount of ice water, adjust the pH to about 8 with dilute hydrochloric acid, a large amount of solid precipitates, filter and dry to obtain 21.56g of yellow-white solid (intermediate IQ4).

[0068] POCl 3 and DMF with POCl 3 : The equivalent of DMF = 2.25: 1 was used to generate Vilsmeier reagent under ice bath conditions, then slowly add 1g IQ4 to Vilsmeier reagent, and react at room temperature for 1h, the solution gradually turned reddish brown. Stop the reaction, slowly drop water into the reaction so...

Embodiment 3

[0073] Example 3: DS-B6

[0074] Stir 1.6 g (10 mmol) of indole-2 carboxylic acid in 8 mL of chloroform, slowly add SOCl in an ice-water bath 2 (2.2mL, 30mmol), reacted at 70°C for 1h, removed the solvent under reduced pressure, prepared 8mL of chloroform solution, and slowly added dropwise to the solution containing (1.2mL, 15mmol) pyridine and 3-amino-2-thiophenecarboxylic acid A solution of methyl ester (1.4g, 9mmol) in 8mL of chloroform was reacted at room temperature for 8h. After the reaction, it was allowed to stand, filtered, and air-dried to obtain 2.55 g of a yellow-white solid (intermediate DS1a).

[0075] Stir DS1a (0.3g, 2mmol) in 10mL of ethanol, add 2mo / L NaOH solution, and heat up to 80°C for 1h. After the reaction, the reaction solution was cooled to room temperature, poured into ice water, adjusted to acidic pH with 10% HCl, extracted with ethyl acetate, spin-dried the solvent, and the crude product was washed with a small amount of methanol to obtain 283 m...

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Abstract

The invention relates to an anti-obesity compound and a preparing method and application thereof. The compound structural formula is shown as the formula (I), or the formula (II) or the formula (III).The anti-obesity compound has high lipid-decreasing activity and is capable of effectively suppressing fat cell differentiation and reducing the lipid level in fat cells, high in stability and low intoxicity. In addition, the anti-obesity compound is prepared through a three-step method, the preparing process is simple and short in time and includes few reaction steps, and aftertreatment is easy.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, more specifically, to an anti-obesity compound and its preparation method and application. Background technique [0002] In today's society, the number of obese patients is increasing sharply around the world, showing a clear trend of younger age. Overweight and obesity make the incidence of other chronic non-communicable diseases in my country show an upward trend. Obesity has become a public health problem that affects residents' health. One of the security issues. Studies have shown that the formation of obesity is mainly due to the excessive formation of fat caused by the disorder of the body's metabolic balance, and mediates the disorder of the endocrine system. The formation of white fat is mainly the result of the joint action of many factors, which is mainly manifested as the breakdown of the balance of glucose and lipid metabolism, the enhancement of anabolism and the weakening...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D495/04C07D403/14C07D405/04C07D409/04A61P3/04
CPCC07D403/04C07D403/14C07D405/04C07D409/04C07D495/04
Inventor 黄志纾饶勇徐昭胡宇涛余宏高琳
Owner SUN YAT SEN UNIV
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