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Aryl gemfibrozil derivative hypervalent iodine compound and preparation method thereof

A technology for gemfibrozil and derivatives is applied in the field of aryl gemfibrozil derivatives hypervalent iodine compounds and their preparation, and can solve problems that are not conducive to the construction of gemfibrozil drug libraries and gemfibrozil drug molecules. Limited and narrow scope of application

Active Publication Date: 2021-07-06
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, common gemfibrozil derivatives are modified on the gemfibrozil aryl group by modifying the aliphatic chain hydrocarbon carboxyl group of gemfibrozil or directly performing C-H activation on the gemfibrozil aryl group, but this method Usually requires the use of transition metal catalysts, poor selectivity, narrow scope of application
The gemfibrozil-like drug molecules obtained from the reactions reported above are very limited, which is not conducive to the construction of a huge gemfibrozil-like drug library
Therefore, the synthesis of gemfibrozil derivatives lacks a simple preparation process, good selectivity, and an effective method with a wide range of applications.

Method used

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  • Aryl gemfibrozil derivative hypervalent iodine compound and preparation method thereof
  • Aryl gemfibrozil derivative hypervalent iodine compound and preparation method thereof
  • Aryl gemfibrozil derivative hypervalent iodine compound and preparation method thereof

Examples

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Effect test

Embodiment 1

[0061] The preparation of phenyl gemfibrozil methyl ester hypervalent iodine trifluoromethanesulfonate described in this embodiment comprises the following steps:

[0062] (1) In a 100 mL round bottom flask, add 10 mmol of hydroxy(p-toluenesulfonyloxy)iodobenzene into a mixed solution of 30 mL of dichloromethane and 5 mL of 2,2,2-trifluoroethanol, then Add 10 mmol gemfibrozil methyl ester compound, then add 10 mmol trimethylsilyl trifluoromethanesulfonate dropwise, then react at room temperature for 1 h;

[0063] (2) After the reaction was completed, the solvent was distilled off under reduced pressure, and 70 mL of diethyl ether was added to precipitate to obtain hypervalent iodine trifluoromethanesulfonate as a white solid with a yield of 83%.

[0064] figure 1 For the hypervalent iodine trifluoromethanesulfonate of phenyl gemfibrozil methyl ester prepared in Example 1 of the present invention 1 H NMR, figure 2 For the hypervalent iodine trifluoromethanesulfonate of phen...

Embodiment 2

[0068] The preparation of 4-methylphenyl gemfibrozil methyl ester hypervalent iodine trifluoromethanesulfonate described in this embodiment comprises the following steps:

[0069] (1) In a 100 mL round bottom flask, dissolve 10 mmol 4-methyliodobenzene in 40 mL methylene chloride, add 10 mmol m-chloroperoxybenzoic acid and then 10 mmol p-toluenesulfonate under stirring condition Acid monohydrate, stirred at room temperature for 1 h, after the reaction was completed, spin the solvent dry, add 70 mL of ether, stir well for 30 minutes to produce a precipitate, filter and dry in vacuum to obtain hydroxyl (p-toluenesulfonyloxy) 4-methyliodobenzene, the yield is 98%;

[0070] (2) In a 100 mL round bottom flask, add 8 mmol of hydroxy(p-toluenesulfonyloxy)4-methyliodobenzene in step (1) to 25 mL of dichloromethane and 4 mL of 2,2,2- In the mixed solution of trifluoroethanol, add 8 mmol gemfibrozil methyl ester compound subsequently, then add 8 mmol trimethylsilyl trifluoromethanesulf...

Embodiment 3

[0076] The preparation of hypervalent iodine trifluoromethanesulfonate 2,4,6-trimethylphenyl gemfibrozil methyl ester described in this example comprises the following steps:

[0077] (1) In a 250 mL round bottom flask, dissolve 10 mmol of iodine in 100 mL of dichloromethane, add 20 mmol of mesitylene under stirring, then add 30 mmol of m-chloroperoxybenzoic acid and 20 mmol of p-toluene Sulfonic acid monohydrate was reacted at room temperature for 1 hour. After the reaction was completed, the solvent was spin-dried, and 150 mL of diethyl ether was added, and stirred thoroughly for 30 minutes to produce a precipitate, which was filtered and dried in vacuum, and the obtained hydroxyl group (p-toluenesulfonyl Oxygen)-trimethyliodobenzene, the yield is 97%;

[0078] (2) In a 100 mL round-bottomed flask, add 8 mmol of hydroxy(p-toluenesulfonyloxy)-trimethyliodobenzene obtained in step (1) into 25 mL of dichloromethane and 3 mL of 2,2,2- In the mixed solution of trifluoroethanol, ...

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Abstract

The invention discloses an aryl gemfibrozil derivative hypervalent iodine compound and a preparation method thereof. The structural formula of the aryl gemfibrozil derivative hypervalent iodine compound is formula (I). The aryl gemfibrozil derivative hypervalent iodine compound is an efficient electrophilic reagent. The aryl gemfibrozil derivative hypervalent iodine compound can realize nucleophilic substitution reaction of specific sites on aryl of gemfibrozil molecules, and achieves the purposes of modifying the gemfibrozil drug molecules and expanding the types of the gemfibrozil drug molecules. Meanwhile, the invention provides a preparation method of the compound. The method is direct, simple, efficient and suitable for large-scale preparation of the aryl gemfibrozil derivative hypervalent iodine compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, in particular to an aryl gemfibrozil derivative hypervalent iodine compound and a preparation method thereof. Background technique [0002] Gemfibrozil belongs to the derivatives of clofibrate and is a commonly used lipid-lowering drug in clinical practice. The pharmacological effects mainly include the protective effect of myocardial ischemia-reperfusion injury, the effect of anti-hepatic fatty disease, the effect of reducing FFA and AFABP, the effect of hypoglycemia and the effect of dilating the aorta. For severe type IV or V hyperlipoproteinemia, coronary heart disease, high risk and ineffective diet control, weight loss; also for type IIb hyperlipoproteinemia, coronary heart disease, high risk and diet control , weight loss, and other blood lipid regulation drug treatment ineffective. Therefore, the field of synthesis of such compounds needs to develop an efficient, sim...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/712C07C67/307C07C59/68C07C51/363C07C309/06C07C303/32
CPCC07C69/712C07C67/307C07C59/68C07C51/363C07C309/06C07C303/32
Inventor 周均吴盼盼陈超陈泗林李冬利张焜
Owner WUYI UNIV
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