Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof

A technology of dihydrochalcone two-carbon glycoside compound and glucosyl dihydrochalcone two-carbon glycoside, which can be applied in the field of medicine and can solve the problems such as failure to achieve success

Active Publication Date: 2020-09-15
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

HSYA was isolated from safflower by Meselhy et al. in 1993. Many research groups at home and abroad have tried to synthesize it, but unfortunately they have not succeeded.

Method used

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  • Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof
  • Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof
  • Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] The synthetic method of compound 1, comprises the following steps:

[0059] (1) Synthesis of 2,4,6-trihydroxydihydrochalcone

[0060] Take phloroglucinol (5.0g, 40mmol) and phenylpropionic acid (6.0g, 40mmol) in a 100mL double-necked bottle, add boron trifluoride in ether solution (26mL, 200mmol), under nitrogen protection, at 85°C Stir the reaction for 4h, lower to room temperature, pour the reaction solution into 10% sodium acetate aqueous solution (200mL), let it stand for 4h, extract three times with ethyl acetate, 200mL each time, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter In addition to the desiccant, concentrated under reduced pressure to obtain the crude product, silica gel column chromatography, the eluent is petroleum ether / ethyl acetate = 5:1, 5.36g of 2,4,6-trihydroxydihydrochalcone was obtained, and the yield was 52%; the process takes place as follows:

[0061]

[0062] The structural characterizat...

Embodiment 2

[0071] The synthetic method of compound 2, comprises the following steps:

[0072] (1) Synthesis of 2,4,6,13-tetrahydroxydihydrochalcone

[0073] Take phloroglucinol (5.0g, 40mmol) and p-hydroxyphenylpropionic acid (6.24g, 40mmol) in a 100mL two-necked bottle, add boron trifluoride in ether solution (26mL, 200mmol), under air protection, 85°C Stir the reaction for 4 h under the conditions, lower to room temperature, pour the reaction solution into 10% sodium acetate aqueous solution (200 mL), let it stand for 4 h, extract three times with ethyl acetate, 200 mL each time, combine the organic phases, wash with saturated brine, and dry over anhydrous sodium sulfate , filtered off the desiccant, and concentrated under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography, and the eluent was petroleum ether / ethyl acetate=3:1 to obtain 6.58 g of 2,4,6,13-tetrahydroxydihydrochalcone , the productive rate is 60%; The process takes place i...

Embodiment 3

[0085] The synthetic method of compound 3 comprises the following steps:

[0086] (1) Synthesis of 2,4,6-trihydroxy-13-methoxydihydrochalcone

[0087] Take phloroglucinol (5.0g, 40mmol) and p-methoxyphenylpropionic acid (7.2g, 40mmol) in a 100mL double-necked bottle, add boron trifluoride ether solution (26mL, 200mmol), under nitrogen protection, Stir the reaction at 85°C for 4 hours, cool down to room temperature, pour the reaction solution into 10% sodium acetate aqueous solution (200mL), let stand for 4h, extract three times with ethyl acetate, 200mL each time, combine the organic phases, wash with saturated brine, anhydrous sulfuric acid Drying over sodium, filtering off the desiccant, and concentrating under reduced pressure to obtain the crude product, silica gel column chromatography, the eluent is petroleum ether / ethyl acetate = 4:1, to obtain 2,4,6,13-tetrahydroxydihydrochalcone 7.49g, productive rate is 65%; This process takes place following reaction:

[0088] ...

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Abstract

The invention discloses a class of quinoid dihydrochalcone C-glycoside compounds with glucose on a ring A, a preparation method and anti-cerebral ischemia injury activity thereof, wherein the compoundhas a structure represented by a general formula (I). The preparation method of the compound comprises the following steps: (1) synthesizing a 2,4,6-trihydroxy dihydrochalcone compound; (2) synthesizing a 2,4,6-trihydroxy-3,5-diglucosyl dihydrochalcone C-glycoside compound; and (6) synthesizing a class of quinoid dihydrochalcone C-glycoside compound with glucose in the A ring. The compound disclosed by the invention is simple in preparation method and has a remarkable effect of resisting cerebral ischemia injury.

Description

technical field [0001] The invention relates to the field of medicine, a class of compounds having a quinoidal chalcone dicarboside structure of glucose in the A ring, a preparation method, a pharmaceutical composition containing them and their application in ischemic stroke. Background technique [0002] Ischemic stroke is a major disease that seriously threatens human health and social development. Studies have shown that 1.5 million people die of stroke every year in China, and three-quarters of the survivors suffer from disabilities of varying degrees. With the rapid development of medical science and technology, although the level of diagnosis and treatment of cerebrovascular disease is constantly improving, the disease still has the characteristics of high incidence, high recurrence rate, high disability rate and high mortality rate. Therefore, it is more and more urgent to further study the pathogenesis of ischemic cerebrovascular disease and develop effective therap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/10A61K31/351A61P9/10
CPCC07D309/10A61P9/10
Inventor 张培成彭英高万杨桠楠姜建双冯子明周昱君
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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