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Compound, and preparation method and application thereof

A compound and reaction technology, applied in the field of compounds and their preparation, can solve the problems of low yield, difficult synthesis and the like

Active Publication Date: 2016-08-31
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The three α-glucosidase inhibitors currently on the market are difficult to synthesize and have low yields

Method used

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  • Compound, and preparation method and application thereof
  • Compound, and preparation method and application thereof
  • Compound, and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0111] The processing steps of its synthetic method are:

[0112] Dissolve 2mmol of 3,4-dimethoxyacetophenone in 10mL of methanol, add 0.2mL of 50% KOH aqueous solution, heat at 70°C, dissolve 1mmol of p-benzaldehyde in 10mL of methanol, then add dropwise 3,4-dimethyl oxyacetophenone solution. After reacting for 2 h, stop heating, pour the reaction solution into water, and remove methanol by rotary evaporation, CH 2 Cl 2 Extraction, CH 3 COOCH 2 CH 3 :CH 2 Cl 2 =1:100 ccy-6 was obtained by column chromatography. Ice-water bath, under the protection of nitrogen atmosphere, inject 5ml 1mol / L BBr into the two-necked bottle 3 CH 2 Cl 2 solution, 0.3 mmol ccy-6 dissolved in 15 ml dry CH 2 Cl 2 and dropwise into BBr 3 In solution, ccy-6 and BBr 3 The molar ratio is 1 / 17. After reacting at 0-35°C for 24-48 hours, the solution is poured into ice water, stirred while pouring, and the solid is filtered, dried, and washed with methanol to obtain compound ccy-7.

[0113] Th...

Embodiment 1

[0142] Embodiment 1 compound ccy-7 and its synthesis

[0143] Dissolve 364mg (2mmol) of 3,4-dimethoxyacetophenone in 3mL of methanol, add 0.2Ml 50% KOH aqueous solution, heat at 70°C, dissolve (134mg) 1mmol of p-benzaldehyde in 4mL of methanol and add dropwise 3 , 4-dimethoxyacetophenone solution. After reacting for 2 h, stop heating, pour the reaction solution into water, and remove methanol by rotary evaporation, CH 2 Cl 2 Extraction, CH 3 COOCH 2 CH 3 :CH 2 Cl 2 =1:10~1:20 Column chromatography separation obtained 353mg ccy-6, yield 77%. Ice-water bath, nitrogen atmosphere protection, inject 5ml 1mol / L BBr into a 100ml two-necked bottle 3 CH 2 Cl 2 solution, 137mg (0.3mmol) ccy-6 dissolved in 15ml dry CH 2 Cl 2 and dropwise into BBr 3 In solution, ccy-6 and BBr 3 The molar ratio was 1 / 17. After reacting at 25°C±5°C for 24h, the solution was poured into ice water, stirred while pouring, filtered to obtain a solid, and the filter residue was dried, and column ch...

Embodiment 2

[0147] Embodiment 2 compound ccy-9 and its synthesis

[0148] 339 mg (2 mmol) of 3,4-dimethoxybenzaldehyde and 160 mg (1 mmol) of m-benzophenone were reacted to obtain 185 mg of ccy-8 with a yield of 41%. 188mg (0.4mmol) ccy-8 and 4.5ml 1mol / L BBr 3 CH 2 Cl 2 Solution reaction, ccy-8 and BBr3 The molar ratio of ccy-9 is 1 / 11, and the reaction conditions and synthesis method are the same as in Example 1 to obtain 100 mg ccy-9 with a yield of 61%. The product was tested by IR spectrum and 1 H NMR spectrum measurement, analysis result is as follows:

[0149] IR spectrum (KBr coating cm- 1 ): 3448,1654,1597,1514,1437,1367,1284,1167,1103,1061,978,790,678,567.

[0150] 1 H NMR Spectrum (ppm): (300MHz, DMSO) δ9.74(s, 2H), 9.13(s, 2H), 8.61(s, 1H), 8.32(dd, J=7.8, 1.5Hz, 2H), 7.71 (t,J=7.8Hz,1H),7.65(s,4H),7.28(d,J=1.8Hz,2H),7.19(dd,J=8.4,2.1Hz,2H),6.80(d,J= 8.1Hz,2H),6.80(d,J=8.1Hz,2H).

[0151] (solvent DMSO-d 6 , TMS internal standard)

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Abstract

The invention relates to the field of chemical engineering, in particular to a compound and a preparation method thereof. The compound has high alpha-glucosaccharase inhibitory activity and can be used for preparing blood glucose reduction drugs. According to the preparation method, a double-chalcone type alpha-glucosaccharase inhibitor can be obtained through two-step reaction, and accordingly, reaction steps are simple. In-vitro pharmacological experiments show that the compound has a certain inhibition effect on alpha-glucosaccharase. Cellular level detection shows that the compound does not obviously affect ingestion activities of HepG-2 cells from exogenous glucose; a compound ccy-13 (1 micrometer) can obviously (p<0.05) reduce the glucose content (about 40%) of the cells, close to a positive control group PG (5 micrometers), thereby having high alpha-glucosaccharase inhibitory activity. The compound can be used for preparing the blood glucose reduction drugs.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to compounds and their preparation methods and applications. Background technique [0002] Chalcones are a class of natural compounds widely present in licorice, safflower, Oxytropis falciparum and other plants. They have various pharmacological activities and are widely used in daily production as organic pigments. [0003] In terms of structure, because chalcone compounds have greater flexibility and can bind to different receptors, they have a wide range of biological activities, such as anti-tumor, anti-inflammatory, anti-fungal, anti-viral, etc. Therefore, chalcones have potential value for drug development. Sofalcone, a new anti-gastric ulcer drug that has been used clinically in Japan, is a chalcone compound modified with prenyl ether. It has strong anti-Helicobacter pylori (H.pylori) activity and can regulate gastric acid secretion. And it can increase the content of pros...

Claims

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Application Information

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IPC IPC(8): C07C49/835C07C45/64A61K31/12A61P3/10
CPCC07C49/835
Inventor 汪波蔡超云郭锦轩饶勇肖志尊曹警予
Owner SUN YAT SEN UNIV
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