Flavone skeleton transition derivative and medical application thereof

A technology of skeleton transition and derivatives, applied in the field of medicine, can solve problems such as difficulty in lasting curative effect

Pending Publication Date: 2020-11-24
TIANJIN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the existing chemical drugs developed based on a single target point have a relatively clear mechanism of action, because diabe

Method used

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  • Flavone skeleton transition derivative and medical application thereof
  • Flavone skeleton transition derivative and medical application thereof
  • Flavone skeleton transition derivative and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1: the preparation method of compound 1

[0014]

[0015] Weigh 5 g of a commercially available pharmaceutical intermediate (CAS 110683-23-3) and suspend and disperse it in 30 ml of dichloromethane, add 6 ml of triethylamine dropwise with stirring in an ice bath, and then add 3.5 g of 4-dimethylaminopyridine. Weigh 12g in a small beaker, dissolve it completely with 10ml of dichloromethane, slowly add di-tert-butyldicarbonate solution in dichloromethane (12g / 10ml) dropwise into the reaction flask, and stir the reaction solution at 30°C after the dropwise addition 12h. After the TLC monitoring reaction was complete,

[0016] Add 3 mol / L hydrochloric acid solution to the reaction solution until the solution pH=3-4. The organic layer was washed three times with water until the aqueous layer was colorless, and the organic layer was concentrated to obtain a black paste. A large amount of methanol was added to suspend the paste, and a large amount of yellow pr...

Embodiment 2

[0018] Embodiment 2: the preparation method of compound 2

[0019]

[0020] Weigh 550 mg of potassium hydroxide and disperse it in 60 ml of methanol solution, add 1.1 g of compound 1 in batches while stirring in an ice bath, stir for 10 minutes, weigh, and slowly add 1 g of diacetoxyiodobenzene in portions under ice bath. After the addition, the reaction temperature was adjusted to 25°C, and the reaction was carried out for 3 hours. After the completion of the reaction was monitored by TLC, methanol was spin-dried to remove, redissolved with ethyl acetate, and the organic layer was washed three times with water; the organic layer was dried, filtered, and concentrated to obtain compound 2 as a white solid with a yield of 82%. 1 H-NMR (400MHz, CDCl 3 ) δ8.16(1H, d, J=6.8Hz), 7.42(1H, s), 7.25(1H, m), 7.04(1H, m), 3.35(3H, s, OCH3), 3.32(3H, s , OCH3), 3.26 (3H, s, OCH3), 1.78 (9H, s), 1.54 (9H, s).

Embodiment 3

[0021] The preparation method of embodiment 3 compound 3

[0022]

[0023] Add appropriate amount of acetone to dissolve 1 g of compound 2, keep stirring at 30°C for reaction, then add 10 ml of concentrated hydrochloric acid, and react for 5 h. After the TLC monitoring reaction was complete,

[0024] Add 20ml of ethyl acetate to the reaction solution, a large amount of flocculent precipitates appeared, filter with suction, and wash the filter cake with water to obtain compound 3 as a bright yellow solid. Yield 71% 1 H-NMR (400MHz, CDCl 3 )δ7.76(1H, s), 7.60(1H, d, J=8.04Hz), 7.22(1H, m), 7.06(1H, d, J=7.64Hz), 1.68(9H, s).

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Abstract

The invention provides a flavone skeleton transition derivative and a medical application thereof, and belongs to the technical field of medicines. Specifically, the invention relates to a compound asshown in a formula I, and the compound has anti-diabetes and anti-obesity effects. An experiment result of a DIO obese mouse model shows that the derivative as shown in the formula I can remarkably reduce the weight of a DIO obese mouse in a dose-dependent manner and remarkably reduce the waist fat volume rate of the obese mouse in a dose-dependent manner, and has a definite anti-obesity effect.On the other hand, the compound as shown in the formula I can significantly reduce fasting blood glucose of the DIO mouse in a dose-dependent manner, and significantly reduce plasma insulin level, total cholesterol, MDA, glycosylated hemoglobin and sugar tolerance of the model mouse in a dose-dependent manner, wherein the glycosylated hemoglobin can effectively reflect the blood glucose control condition of a diabetes patient in the past 1-2 months, is a gold standard for measuring blood glucose control, and has a remarkable anti-diabetes effect.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a flavone skeleton transition derivative and its medical application. Background technique [0002] Diabetes is a chronic lifelong disease that seriously endangers human health. It is an endocrine and metabolic disease characterized by high blood sugar and multiple complications caused by absolute or relative insulin deficiency. It is mainly divided into type 1 and type 2 diabetes. . Since the beginning of the 21st century, the incidence of diabetes has been increasing year by year due to the aging trend of the population and the lack of awareness of people's health care, leading to excessive intake of high-calorie foods, and it has become a major disease worldwide. According to the statistics of the International Diabetes Federation (IDF) in 2017, there are about 425 million adults with diabetes in the world, of which 114.4 million are diabetics in my country aged ...

Claims

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Application Information

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IPC IPC(8): C07D405/04A61P3/10A61P3/04
CPCA61P3/04A61P3/10C07D405/04
Inventor 段宏泉秦楠陈莹吴潇然成冯波
Owner TIANJIN MEDICAL UNIV
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