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Nine PTP1B inhibitors and synthesis method and application thereof

An inhibitor, chemical synthesis technology, used in oxime preparation, drug combination, carboxylate preparation and other directions

Inactive Publication Date: 2017-01-04
南通中国科学院海洋研究所海洋科学与技术研究发展中心 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are insulin sensitizers that can improve metabolism in type 2 diabetes, PTP1B inhibitors do not have side effects such as fluid retention, weight gain, and obesity when PTP1B inhibitors improve metabolism. An important target in type 2 diabetes

Method used

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  • Nine PTP1B inhibitors and synthesis method and application thereof
  • Nine PTP1B inhibitors and synthesis method and application thereof
  • Nine PTP1B inhibitors and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1 "5-[3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzylidene]thiazolidine-2 , 4-diketone (1) and 5-[3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyl]thiazole Total Chemical Synthesis and Structure Identification of Alkane-2,4-dione(2),"

[0072] (1) Chemical Synthesis and Structure Identification of 5-Bromovanillin

[0073] At 0°C, add 2.8mL of Br2 dropwise to 60mL of methanol with 7.6g (0.05mol) of vanillin dissolved therein, and finish adding in 2 hours, stir at room temperature for 1 hour, then add 25mL of water dropwise thereto at 0°C (with Precipitation), after 20 minutes of adding, continue to stir for 15 minutes, filter the precipitate, wash the precipitate with ice water, and drain to obtain 10.7 g of white crystals. After spectral analysis, it is confirmed that the compound is 5-bromovanillin;

[0074]The physical and chemical properties of the compound are as follows: white crystals, melting point 160-162°C; proton nuclea...

Embodiment 2

[0103] Example 2 "5-{4-[3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyloxy]phenylene Methyl}thiazolidine-2,4-dione, 5-{4-[3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-di Chemical Total Synthesis and Structure Identification of Methoxybenzyloxy]phenyl}thiazolidine-2,4-dione

[0104] (1) 4-[3-bromo-2-(2′,3′-dibromo-4′,5′-dimethoxybenzyl)-4,5-dimethoxybenzyloxy]-benzene Chemical Synthesis and Structure Identification of Formaldehyde

[0105] Add 1.03 g of compound 17 to the reaction flask, dissolve in 10 mL of acetone, then add 0.306 g of p-hydroxybenzaldehyde and 0.462 g of K 2 CO 3 , TLC detection reaction process. After the reaction was completed, suction filtration was performed, and the filtrate was concentrated under reduced pressure. The oil was separated by column chromatography, and the eluent was petroleum ether: ethyl acetate = 6:1 to obtain 1 g of white solid.

[0106] The physical and chemical properties of the compound are as follows: white p...

Embodiment 3

[0113] Example 3 Chemical synthesis and structure of "3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyl-ethyl oxalate" identification

[0114] (1) Synthesis and structure identification of 3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyl-ethyl oxalate

[0115] Under ice bath conditions, 1 g of compound 18 was added to the reaction flask, dissolved in dichloromethane, then 119 mg of 4-dimethylaminopyridine (DMAP) was added, and 0.4 mL of ethyl oxalyl chloride was added. The progress of the reaction was detected by TLC. After the reaction was complete, the reaction solution was added into an equal volume of water and dichloromethane, and the organic phase was washed with saturated NaHCO3 and dried over anhydrous Na2SO4. The obtained oil was separated by column chromatography, and the eluent was petroleum ether: ethyl acetate = 4:1 to obtain 1.67 g of white solid.

[0116]The physical and chemical properties of the compound are as follows: white so...

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Abstract

The invention relates to a chemical total synthesis method of nine novel PTP1B inhibitors and application of the nine novel PTP1B inhibitors in medicine for treating type 2 diabetes. According to the PTP1B inhibitors, one or two or more of nine compounds serve as active ingredients, and the structural formulas of the nine compounds are shown in the specification. By means of the compounds, the sensitivity of insulin receptors can be enhanced by inhibiting the activity of PTP1B, and a good treatment effect is achieved for insulin resistance type 2 diabetes.

Description

technical field [0001] The present invention relates to biomedicine, specifically nine brominated compounds 5-[3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethyl Oxybenzylidene]thiazolidine-2,4-dione (1), 5-[3-bromo-2-(2,3-dibromo-4,5-dimethoxybenzyl)-4 ,5-Dimethoxybenzyl]thiazolidine-2,4-dione (2),5-{4-[3-bromo-2-(2,3-dibromo-4,5-dimethoxy benzyl)-4,5-dimethoxybenzyloxy]benzylidene}thiazolidine-2,4-dione (3), 5-{4-[3-bromo-2-(2, 3-Dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyloxy]phenyl}thiazolidine-2,4-dione (4),3-bromo-2 -(2,3-Dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyl-ethyl oxalate (5), 3-[3-bromo-2-(2 ,3-Dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyloxy]-3-oxopropionic acid (6), 3-bromo-2-(2, 3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzaldehyde oxime (7), 2,3-dibromo-1-{2-bromo-3,4- Dimethoxy-6-[(4-nitrophenoxy)methyl]phenyl}-4,5-dimethoxydimethoxybenzene (8), 4-[3-bromo-2- (2,3-dibromo-4,5-dimethoxybenzyl)-4,5-dimethoxybenzyloxy]aniline (9) and ...

Claims

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Application Information

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IPC IPC(8): C07C251/48C07C249/08C07D277/34C07C69/36C07C69/38C07C67/14C07C67/08C07C205/37C07C201/12C07C217/86C07C213/02A61P3/10
Inventor 史大永江波王立军吴宁王帅玉李祥乾杨猛
Owner 南通中国科学院海洋研究所海洋科学与技术研究发展中心
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