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Structure of quinoxalinone derivatives as aldose reductase inhibitor, preparation method and use

A technology of structural formula and raw materials, applied in the prevention and/or treatment of diabetic complications, structure and preparation field of aldose reductase inhibitors, can solve problems such as insufficient activity intensity, and achieve good inhibitory effect

Inactive Publication Date: 2015-05-20
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As natural antioxidants, flavonoids have been found to have aldose reductase inhibitory activity, but their activity intensity is not enough to obtain further development

Method used

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  • Structure of quinoxalinone derivatives as aldose reductase inhibitor, preparation method and use
  • Structure of quinoxalinone derivatives as aldose reductase inhibitor, preparation method and use
  • Structure of quinoxalinone derivatives as aldose reductase inhibitor, preparation method and use

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preparation example Construction

[0050] see figure 1 , the embodiment of the present invention provides a class of a class of quinoxalinone derivatives as the structure of an aldose reductase inhibitor and a preparation method thereof, which includes the following steps:

[0051] S2: the chlorination reagent used in the reaction can also be phosphorus oxychloride, phosphorus oxychloride, etc. in addition to thionyl chloride, and the reaction temperature is 40°C-50°C;

[0052] S3: The alkali used in the reaction, in addition to lithium hydroxide, can also be sodium hydroxide, potassium hydroxide, potassium carbonate, etc., and the reaction temperature is 55°C-75°C;

[0053] S5: the catalyst used in the reaction, except palladium acetate and tri-o-methylphenylphosphine, can also be tetrakistriphenylphosphine palladium, palladium acetate and triphenylphosphine, palladium chloride and triphenylphosphine, Palladium chloride and trimethylphenylphosphine etc.; The alkali used in the described reaction, except tr...

Embodiment 1

[0055] Example 1: Preparation of 2-(3-(3,4-dihydroxystyryl)-2-oxoquinoxaline-1(2H)-alkyl)acetic acid

[0056] (compound 1)

[0057]

[0058] Put 10.8g (100mmol) of o-phenylenediamine and 13.5g (150mmol) of oxalic acid into a round bottom flask, then add 100mL of water and 10mL of concentrated hydrochloric acid, heat, stir and reflux for 6 hours, and after returning to room temperature, filter the reaction solution, Repeated washing with water and drying gave quinoxaline-2,3(1H,4H)-dione (colorless crystals, yield 96%, 15.6g): 1 H NMR (400MHz, [D 6 ]DMSO): δ 7.063 (d, 2H, J = 6.4Hz), 7.114 (d, 2H, J = 6.4Hz), 11.893 (s, 2H).

[0059] Add 8.1g (50mmol) of quinoxaline-2,3(1H,4H)-dione, 11.9g (100mmol) of thionyl chloride, and 5mL of DMF into a round-bottomed flask containing 50mL of dichloromethane, and heat to reflux Stir until the starting material spot disappears as monitored by TLC. The reaction solution was cooled to room temperature, and poured into ice water careful...

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Abstract

The invention provides a structure of compounds shown in a formula I, a preparation method, and use of pharmaceutically acceptable salts or a mixture thereof in preparation of medicines for preventing and / or treating diabetic complication. The compounds as an aldose reductase inhibitor and an antioxidant effectively eliminate free radicals and inhibit generation of lipid peroxide by inhibiting the activity of aldose reductase so as to play a role of preventing and / or treating diabetic complication. The invention further provides pharmaceutical compositions which comprise the compounds and play a role of preventing and / or treating diabetic complication. The formulae are shown in the description.

Description

technical field [0001] The present invention relates to the fields of organic chemistry, medicinal chemistry and pharmacotherapy, in particular to the structure, preparation method, inhibitory effect on aldose reductase (Aldose Reductase, ALR2) of a class of novel aldose reductase inhibitors and the prevention of And / or applications in the treatment of diabetic complications. Background technique [0002] Diabetes Mellitus (DM) is a worldwide disease that seriously endangers human health. The danger of diabetes mainly lies in its complications. Diabetic complications include metabolic syndromes such as nephropathy, retinopathy, neurological diseases and cardiovascular and cerebrovascular diseases. Due to the high disability rate and high mortality rate of diabetes complications, it has become one of the main threats to the health and life expectancy of residents in most countries in the world. However, there are almost no drugs for diabetic complications in the world at pr...

Claims

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Application Information

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IPC IPC(8): C07D241/44A61K31/498A61P3/10
CPCC07D241/44
Inventor 朱长进马兵秦祥宇
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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