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Coumarin-isatin type compounds, and preparation method and purpose thereof

A compound, coumarin technology, applied in organic chemistry, drug combination, metabolic diseases, etc., can solve the problems of high toxicity and side effects, low activity, hindering application, etc., and achieve a good effect of inhibiting activity

Active Publication Date: 2016-01-13
贺州市八步区市场监督管理局
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing α-glucosidase inhibitors have disadvantages such as low activity and high toxicity and side effects, which hinder their clinical application.

Method used

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  • Coumarin-isatin type compounds, and preparation method and purpose thereof
  • Coumarin-isatin type compounds, and preparation method and purpose thereof
  • Coumarin-isatin type compounds, and preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Preparation of ethyl 2-((2-oxo-2H-benzopyran-7-yl)oxy)acetate

[0021]

[0022] Put 7-hydroxycoumarin (1.62g, 10mmol), ethyl bromoacetate (1.84g, 11mmol), potassium carbonate (4.15g, 30mmol) in a round bottom flask, add acetone 100mL, reflux for 6 hours, TLC It shows that the reaction is complete, stop the reaction, cool to room temperature, remove potassium carbonate by filtration, spin the filtrate to dryness, and recrystallize with ethanol to obtain a white solid powder with a yield of 86.4%. m.p.107-110 o c.

Embodiment 2

[0023] Example 2: Preparation of 2-((2-oxo-2H-benzopyran-7-yl)oxy)acetohydrazide

[0024]

[0025] Place ethyl 2-((2-oxo-2H-benzopyran-7-yl)oxy)acetate (2.48g, 10mmol), hydrazine hydrate (1.0g, 20mmol) in a round bottom flask , add 100mL ethanol, reflux reaction, TLC shows that the reaction is complete, stop the reaction, cool to room temperature, filter to obtain a white solid powder, the yield is 65.3%. m.p.171-175 o c.

Embodiment 3

[0026] Example 3: (Z)-2-((2-oxo-2H-benzopyran-7-yl)oxy)-N'-(2-oxoindolane-3-ylidene)acetyl Preparation of hydrazine (1)

[0027]

[0028] Put 2-((2-oxo-2H-benzopyran-7-yl)oxy)acetohydrazide (234mg, 1mmol), isatin (147mg, 1mmol) in a round bottom flask, add 10mL of methanol and A drop of glacial acetic acid was refluxed for 2 hours to stop the reaction, cooled to room temperature, and filtered to obtain a yellow solid powder with a yield of 87.4%. m.p.237-243 o C; 1 HNMR(d 6 -DMSO,400MHz)δ:5.01(s,2H),6.32(d,1H,J=9.6Hz),6.94(d,1H,J=8.0Hz),7.05-7.10(m,3H),7.37(d ,1H,J=8.4Hz),7.58-7.68(m,2H),8.00(d,1H,J=9.6Hz),10.23(s,1H),11.32(s,1H).

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PUM

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Abstract

The invention discloses a kind of coumarin-isatin type compounds, and a preparation method and a purpose thereof. The compounds possess a structure shown as a formula (I). The preparation method comprises taking 7-hydroxycoumarin and ethyl bromoacetate as raw materials to obtain [(2-oxo-2H-chromen-7-yl)oxy]acetic acid, and then performing hydrazinolysis reaction to obtain [(2-oxo-2H-chromen-7-yl)oxy]acetohydrazide, and finally reacting with various substituted isatins to obtain the corresponding target compounds. The compounds can be used as a raw material of an anti-diabetes medicament, and the preparation method is simple and easily-available in raw material and convenient to operate.

Description

technical field [0001] The present invention relates to a class of coumarin-isatin compound, its preparation method and its application as alpha-glucosidase inhibitor in antidiabetic medicine. Background technique [0002] Diabetes is a disease that seriously threatens human life and health. With the continuous improvement of people's living standards, the global incidence of diabetes has been showing an increasing trend year by year. Diabetes mellitus is a metabolic disorder. The main cause is insufficient insulin secretion or the failure of insulin secretion due to the damage of pancreatic islet function. The metabolic syndrome is characterized by persistent high blood sugar as the main biochemical feature. Sustained hyperglycemia is also the main cause of eye, kidney, nerve, cardiovascular and other system lesions. Therefore, controlling hyperglycemia in patients is of great significance for the treatment of diabetes and the prevention of complications caused by diabetes...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61P3/10
CPCC07D405/12
Inventor 王广成彭知云何典雄颜呈波刘文超
Owner 贺州市八步区市场监督管理局
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