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A kind of 1,2,4-triazine-coumarin type compound and its preparation method and application

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

Active Publication Date: 2018-05-22
南京润瞳畅达医药科技有限公司
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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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  • A kind of 1,2,4-triazine-coumarin type compound and its preparation method and application
  • A kind of 1,2,4-triazine-coumarin type compound and its preparation method and application
  • A kind of 1,2,4-triazine-coumarin type compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: 7-(3-((5,6-di(furan-2-yl)-1,2,4-triazin-3-yl)thio)-2-hydroxypropoxy)-2H - Preparation of benzopyran-2-one (1)

[0020]

[0021] Step 1: Put 7-hydroxycoumarin (0.58 g, 3.6 mmol), epichlorohydrin (4.75 g, 51.3 mmol), potassium hydroxide (0.25 g, 4.5 mmol) in a round bottom flask, add ethanol, The reaction was refluxed for 5 h, TLC showed that the reaction was complete, the reaction was stopped, cooled to room temperature, the filtrate was spin-dried, separated and purified by silica gel chromatography to obtain a white solid powder 7-(oxirane-2-ylmethoxy)-2H- Benzopyran-2-one, yield 96%.

[0022] Step 2: Mix 1,2-bis(furan-2yl)-ethane-1,2-dione (0.95 g, 5 mmol), thiosemicarbazide (0.46 g, 5 mmol), potassium carbonate (1.04 g , 7.5 mmol) in a round-bottomed flask, add 50 mL of water, reflux for 16 h, TLC shows that the reaction is complete, stop the reaction, cool to room temperature, adjust the pH to 5 with glacial acetic acid, and filter to obtain Brown-r...

Embodiment 2

[0025] Example 2: 7-(3-((5,6-diphenyl-1,2,4-triazin-3-yl)thio)-2-hydroxypropoxy)-2H-benzopyran - Preparation of 2-ketone (2)

[0026]

[0027] Yield 86%. 1 H NMR (d 6 -DMSO, 400 MHz) δ: 3.46 (dd, 1H), 3.65 (dd, 1H),4.15 (m, 3H), 5.69 (s, 1H), 6.28 (d, 1H), 6.92 (dd, 1H), 6.97 (d, 1H), 7.35(m, 10H), 7.60 (d, 1H), 7.97 (d, 1H); EIMS m / z = 484 [M + ].

Embodiment 3

[0028] Example 3: 7-(3-((5,6-bis(3-fluorophenyl)-1,2,4-triazin-3-yl)thio)-2-hydroxypropoxy)-2H - Preparation of benzopyran-2-one (3)

[0029]

[0030] Yield 80%. 1 H NMR (d 6 -DMSO, 400 MHz) δ: 3.45 (dd, 1H), 3.64 (dd, 1H),4.12 (m, 3H), 5.70 (s, 1H), 6.27 (d, 1H), 6.91 (dd, 1H), 6.96 (d, 1H), 7.23(m, 6H), 7.42 (m, 2H), 7.59 (d, 1H), 7.97 (d, 1H); EIMS m / z = 520 [M + ].

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Abstract

The invention discloses a 1, 2, 4-triazine-coumarin compound and a preparation method and application thereof. The compound is of the structure as indicated in the formula (I), and the preparation method comprises the steps that 7-umbelliferone and epoxy chloropropane serve as raw materials, 7-(oxirane-2-methoxyl)-2H-benzopyran-2-ketone is obtained, 1, 2-diphenylethane-1, 2-diketone and thiosemicarbazide serve as raw materials, 5, 6-diaryl-1, 2, 4-triazine-3-thioalcohol is obtained, and finally 7-(oxirane-2-methoxyl)-2H-benzopyran-2-ketone reacts with all types of 5, 6-diaryl-1, 2, 4-triazine-3-thioalcohol, so that the target compound is obtained. The compound can serve as the raw material of anti-diabetic medicine, the preparation method is simple, raw materials are easy to obtain, and operation is convenient.

Description

technical field [0001] The invention relates to a 1,2,4-triazine-coumarin type compound, its preparation method and its application as an alpha-glucosidase inhibitor in antidiabetic drugs. 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. α...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C07D405/14A61P3/10
CPCC07D405/12C07D405/14
Inventor 董泽贤
Owner 南京润瞳畅达医药科技有限公司
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