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2-substituted vinylsulfonate compound and preparation method and use thereof

A technology for ethylene sulfonate and compound, which is applied in the field of 2-substituted ethylene sulfonate compound and its preparation, and can solve problems such as large toxic and side effects

Inactive Publication Date: 2012-04-11
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Most of the traditional compounds that inhibit PTP1B have multiple phosphate groups as the head. Although this type of compound has good activity, but at the same time, this type of compound has a lot of side effects. We guess it is due to the presence of multiple phosphate groups It can induce the action of multiple phosphorylases in multiple tissues in vivo and induce different side effects

Method used

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  • 2-substituted vinylsulfonate compound and preparation method and use thereof
  • 2-substituted vinylsulfonate compound and preparation method and use thereof
  • 2-substituted vinylsulfonate compound and preparation method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0058] Synthesis of 2-(5-methyl-2-phenyloxazol-4-yl)methyl acetate II ( figure 1 ): Dissolve methyl 4-bromo-3-oxopentanoate (10g, 45mmol) in toluene (200ml), then add benzamide (5.45g, 45mmol) in batches, and reflux for 12 hours after the addition. After the reaction was completed, it was filtered and concentrated under reduced pressure, and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain methyl 2-(5-methyl-2-phenyloxazol-4-yl)acetate 4.4 g (yellow oil, yield 40%). 1 H NMR ((CD 3 ) 2 CO; 300MHz), δ H : 2.378 (s, 3H, CH 3 ), 3.587 (s, 2H, CH 2 ), 3.665 (s, 3H, OCH 3 ), 7.473-7.499 (m, 3H, ArH), 7.950-7.982 (m, 2H, ArH).

Embodiment 2

[0060] Synthesis of 2-(5-methyl-2-phenyloxazol-4-yl)ethanol III ( figure 1 ): Dissolve lithium aluminum tetrahydride (207.1mg, 5.45mmol) in anhydrous ether (20ml), add 2-(5-methyl-2-phenyloxazol-4-yl) dropwise at -5°C Diethyl ether solution of methyl acetate (890mg, 3.63mmol), after the dropwise addition, was stirred at room temperature for half an hour. After the reaction was completed, a saturated ammonium chloride aqueous solution was added dropwise to the reaction system to quench until white flocs appeared in the reaction system. Filter, wash the aqueous phase with ethyl acetate, combine the organic phases, wash with saturated brine three times, and dry over anhydrous sodium sulfate. Concentration under reduced pressure gave 710 mg of 2-(5-methyl-2-phenyloxazol-4-yl)ethanol (colorless solid, yield 96%). 1 H NMR (CDCl 3 ; 300MHz), δ H : 2.347 (s, 3H, CH 3 ), 2.754-2.792 (t, 2H, CH 2 CH 2 , J=5.7Hz), 3.924-3.963 (t, 2H, CH 2 CH 2 , J=5.8Hz), 6.0-6.5 (brs, 1H, O...

Embodiment 3

[0062] Synthesis of ethyl 2-(5-methyl-2-phenyloxazol-4-yl)methanesulfonate IV ( figure 1 ): Dissolve 2-(5-methyl-2-phenyloxazol-4-yl)ethanol (630mg, 3.1mmol) in dichloromethane (15ml), drop triethylamine (0.64ml, 4.65mmol ), and then methanesulfonyl chloride (0.37ml, 4.65mmol) was added dropwise to the reaction system at 0°C, and stirred at room temperature for 4 hours after the dropwise addition was completed. After the reaction was completed, saturated ammonium chloride aqueous solution was added dropwise to the reaction system to quench, the aqueous phase was washed with ethyl acetate, the organic phases were combined, washed three times with saturated brine, and dried over anhydrous sodium sulfate. Concentrated under reduced pressure and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain 700 mg of ethyl 2-(5-methyl-2-phenyloxazol-4-yl)methanesulfonate (colorless Solid, yield 80%). 1 H NMR (CDCl 3 ; 300MHz), δ H : 2.365 (s, 3H,...

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Abstract

The invention relates to a 2-substituted vinylsulfonate compound, and preparation method and use thereof in the field of chemical industry of drugs. The 2-substituted vinylsulfonate compound has the following structure formula: FORMULA, wherein R1 and R2 are substituted aromatic groups, R3 is alkyl substituted aromatic group, n1 is any one of integers of 1 to 4, n2 is 0, 1 or 2, X is O, substituted alkyl or aromatic group, and Y is any one of O, S, C and NH. The invention also relates to a preparation method of the compound and the use of the compound in preparing drug for inhibiting activity of PTPlB protein. The compound can be used for preparing drug for treating or preventing diabetes or obesity taking PTPlB as target point.

Description

technical field [0001] The invention relates to a compound in the field of pharmaceutical chemical technology and its preparation and application method, in particular to a 2-substituted ethylene sulfonate compound and its preparation method and application. Background technique [0002] In recent years, with the rapid increase in the incidence of type 2 diabetes syndrome and obesity, research on the design of new compounds for the treatment of these diseases has become an urgent need. Type 2 diabetes and obesity are two conditions that are closely related to insulin resistance. Insulin resistance exists in various tissues of the human body, such as muscle, liver, adipose tissue and central nervous system, and plays an important role in glucose homeostasis in the body. Insulin signaling occurs through activation of the insulin receptor, leading to the restoration of insulin receptor substrate proteins, which in turn activate phosphatidylinositol 3-kinase (PI3K), protein kin...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D277/42C07D261/08C07D263/32C07D277/24C07D277/26A61P3/10A61P3/04
Inventor 傅磊刘井宝姜发琴金焱刘晶晶刘文陆
Owner SHANGHAI JIAO TONG UNIV
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