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Application of dihydrofuran-2-ketone compounds in preparing medicament for resisting diabetes mellitus and glucose and lipid metabolism

A technology of ketone compounds and dihydrofuran, which is applied in the field of pharmacy, can solve the problems of ineffective hypoglycemic effect, high toxicity, and many side effects

Inactive Publication Date: 2012-05-16
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the existing drugs and their corresponding targets have their shortcomings, such as high toxicity, many side effects, ineffective hypoglycemic effect, and easy drug resistance. Therefore, it is urgent to develop new drugs for the treatment of diabetes.

Method used

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  • Application of dihydrofuran-2-ketone compounds in preparing medicament for resisting diabetes mellitus and glucose and lipid metabolism
  • Application of dihydrofuran-2-ketone compounds in preparing medicament for resisting diabetes mellitus and glucose and lipid metabolism
  • Application of dihydrofuran-2-ketone compounds in preparing medicament for resisting diabetes mellitus and glucose and lipid metabolism

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: Preparation of 4-(3,4-dimethoxybenzyl)-3-(4-methoxybenzyl)dihydrofuran-2(3H)-one (compound 10a)

[0052]

[0053] 1-1: Preparation of Compound 6a

[0054] 67.6g (0.602mol) potassium tert-butoxide is dissolved in 600ml tert-butanol, dimethyl succinate and 3,4-dimethoxybenzaldehyde (0.602mol) are mixed and dissolved in a small amount of tert-butanol, and then Add it dropwise to the solution of potassium tert-butoxide, control the temperature of the reaction system not higher than 40°C, stir at room temperature for 30 minutes, pour the mixture into water (1000ml), wash with isopropyl ether (500ml), and wash the aqueous phase with concentrated Acidify with hydrochloric acid, extract with ethyl acetate (1000ml), take the ethyl acetate layer, wash with water, and wash with saturated sodium chloride solution once each, dry over anhydrous sodium sulfate, dry the solvent by rotary evaporation to obtain a yellow solid, add 100ml of ether, and oscillate ultrasonicall...

Embodiment 2

[0065] Example 2: Preparation of 4-(3,4-dimethoxybenzyl)-3-(4-hydroxyl-3-methoxybenzyl)dihydrofuran-2(3H)-one (compound 10b)

[0066]

[0067] 2-1: Preparation of Compound 7b

[0068] Dissolve compound 11b (1.88g, 12.3mmol) in 10ml methanol, add K 2 CO 3 (2.1g, 14.8mmol), refluxed for 2h, monitored by TLC, filtered and concentrated after the reaction was complete, the residue was dissolved in chloroform, washed twice with 20ml of water, dried over anhydrous sodium sulfate, and concentrated to obtain compound 7b.

[0069] 2-2: Preparation of compound 10b'

[0070] Compound 10b' was prepared in a similar manner as shown in Example 1.

[0071] 10b': 1 HNMR (300MHz, CDCl 3 ): δ7.25-7.48(m, 5H), 6.79(d, 1H, J=8.2Hz), 6.74(d, 1H, J=9.4Hz), 6.71(d, 1H, J=2.4Hz), 6.59 (dd, 1H, J=1.9, 8.1Hz), 6.52(dd, 1H, J=1.9, 8.1Hz), 6.47(d, 1H, J=1.9Hz), 5.13(s, 2H), 4.07-4.18( m, 1H), 3.80-3.92(m, 1H), 3.85(s, 3H), 3.84(s, 3H), 3.80(s, 3H), 2.90-3.00(m, 2H), 2.42-2.68(m, 4H) ).

[0072...

Embodiment 3

[0074] Example 3: Preparation of 4-(3,4-dimethoxybenzyl)-3-(3,4-dihydroxybenzyl)dihydrofuran-2(3H)-one (compound 10c)

[0075]

[0076] Compound 10c was prepared in a similar manner to Compound 10a in Example 1, except that the corresponding starting reactants were used.

[0077] 10c: 1HNMR (300MHz, CDCl3): δ6.41-6.78(m, 6H), 3.97(dd, J=13.12, J=8.92, 2H), 3.82(s, 3H), 3.81(s, 3H), 3.77 (s, 3H), 3.74 (s, 3H), 3.00-2.85 (m, 2H), 2.67-2.43 (m, 4H).

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Abstract

The invention belongs to the field of pharmacology, in particular relates to application of lignin compounds which use dihydrofuran-2-ketone as a mother nucleus and have a structural formula shown in the specification in preparing a medicament for treating diabetes mellitus and glucose and lipid metabolism, and especially relates to application in II-type diabetes mellitus.

Description

technical field [0001] The present invention belongs to the field of pharmacy, and specifically relates to the use of lignin compounds with dihydrofuran-2-one as the core and derivatives thereof in the preparation of anti-diabetic and glucose and lipid metabolism drugs, especially for type II diabetes, the above-mentioned The compound has significant functions of lowering blood sugar and regulating glucose and lipid metabolism activity. Background technique [0002] Lignin compounds show a wide range of biological activities, such as inhibition of cyclic AMP phosphodiesterase activity, anti-platelet aggregation activity, inhibition of peripheral blood lymphocyte proliferation activity, anti-liver injury activity, anti-viral activity, anti-cancer activity and anti-HIV activity , anti-inflammatory activity, etc. This type of compound also shows good insecticidal activity, and is often used as cough medicine and antiviral drug in traditional Chinese medicine. Patent document U...

Claims

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Application Information

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IPC IPC(8): A61K31/365A61K31/7048A61K31/443A61K31/5377A61K31/404A61P3/10
Inventor 冷颖陶燕铎胡有洪龚键黄淑玲于瑞涛
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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