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Linear furocoumarin derivates, preparation method and application thereof, pharmaceutical compositions containing the derivates

A furanocoumarin and derivative technology, which can be used in drug combinations, pharmaceutical formulations, and medical preparations containing active ingredients, etc., can solve problems such as weakening and blocking of insulin signals

Inactive Publication Date: 2008-11-19
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the specific mechanism is not clear, the weakening or even blockage of insulin signaling in its transduction pathway must be the direct factor

Method used

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  • Linear furocoumarin derivates, preparation method and application thereof, pharmaceutical compositions containing the derivates
  • Linear furocoumarin derivates, preparation method and application thereof, pharmaceutical compositions containing the derivates
  • Linear furocoumarin derivates, preparation method and application thereof, pharmaceutical compositions containing the derivates

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0071] Preparation Example 1 Preparation of Compound 2

[0072] (1) Preparation of 6-hydroxy-7-dimethoxycoumarin (2a)

[0073] For convenience, M in the following structural formula represents Me, that is, methyl.

[0074]

[0075] Methoxychloromethane (0.443mL, 5.84mmol) was added to aescin (520.5mg, 2.92mmol) and potassium carbonate (605mg, 4.38mmol) in N,N-dimethylformamide (14.6mL) solution, and After stirring for 13 hours at -20°C, the reaction solution was diluted with 10 mL of water, and then 1 equivalent of hydrochloric acid was added dropwise at 0°C until the solution changed from yellow to colorless. The aqueous layer was extracted with ethyl acetate (2×10 mL), the organic layers were combined, washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 9: 2 elution) to obtain compound 2a as a yellow solid.

[0...

preparation Embodiment 2

[0096] Preparation Example 2 Preparation of Compound 3

[0097] (1) Preparation of 4-methoxymethyl-7-hydroxycoumarin (3a)

[0098]

[0099] To a mixed solution of resorcinol (5.0g, 30mmol) and concentrated sulfuric acid (100mL) was added dropwise methyl-4-methoxyethyl acetoacetate (4.4g, 30mmol), and stirred at 0°C overnight, After the reaction was complete, the reaction solution was poured into ice water, stirred at room temperature for 1 hour, extracted with ethyl acetate (2×100 mL), combined the organic layers, washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain compound 3a (2.53 g, 38%).

[0100] (2) Preparation of 4-methoxymethyl-4'-methylpsoralen (3)

[0101]

[0102] (a) To an anhydrous acetone solution (100 mL) of 4-methoxymethyl-7-hydroxycoumarin (20.0 mmol) was added 10 g of potassium c...

preparation Embodiment 3

[0106] Preparation Example 3 Preparation of Compound 4

[0107]

[0108] According to the method of Preparation Example 2, using chloroacetophenone instead of monochloroacetone, compound 4 was prepared with a yield of 63%.

[0109] 1 H NMR(300MHz, CDCl 3 )δ: 7.92 (1H, s, 5-H), 7.81 (1H, s, 5'-H), 7.63-7.41 (6H, m, 4'-C 6 H 5 and 8-H), 6.53(1H, s, 3-H), 4.69(2H, s, 4-CH 2 -CH 3 ), 3.53(3H, s, 4-CH 2 CH 3 );

[0110] 13 C NMR(75MHz, CDCl 3 )δ: 130.9(C-1”), 129.2(C-3” and C-5”), 128.0(C-4”), 127.4(C-4” and C-6”), 123.9(C-4 '), 122.2(C-6).

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Abstract

The invention provides a linear furocoumarin derivate with a structure expressed by formula 1, a method for preparing the same, an application of the linear furocoumarin derivate and a drug composition containing the linear furocoumarin derivate. The linear furocoumarin derivate has an activating function to GLUT4 membrane transfer and protein expression, and can be used as drugs for treating diabetes mellitus and complicating diseases of the diabetes mellitus.

Description

Technical field [0001] The present invention relates to the field of medicinal chemistry. Specifically, the present invention relates to a new class of linear furanocoumarin derivatives, preparation methods and uses thereof, and pharmaceutical compositions containing the derivatives. The linear furanocoumarin derivative has an agonistic effect on GLUT4 membrane transfer and protein expression, and can be used as a medicine for treating diabetes and its complications. Background technique [0002] Diabetes (diabetes mellitus) is a group of clinical syndromes caused by the interaction of genetic and environmental factors, due to absolute or relative insufficient insulin secretion and decreased sensitivity of target tissue cells to insulin, causing sugar, protein, fat, water and electrolytes, etc. A series of metabolic disorders. Clinically, hyperglycemia is the main common sign. Prolonged illness can cause multiple system damages. Acute metabolic disorders such as ketoacidosis can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04A61K31/366A61P3/10
Inventor 胡立宏沈旭蒋华良张余马磊
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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