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Kudzu-vine root daidzein-7, 4'-dioxo acetic acid compound and preparation method thereof

A technology of dioxoacetic acid and daidzein, which is applied in food preparation, food science, organic chemistry, etc., can solve the problem of insignificant compound properties, and achieve high pharmacological activity, good reproducibility, and high bioavailability Effect

Inactive Publication Date: 2010-06-30
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] CN101255149A discloses a kind of 7,4'-bis(succinic acid monoester) oxygen ethoxy group-daidzein (DZ5), but the performance of the compound of this invention is not remarkable

Method used

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  • Kudzu-vine root daidzein-7, 4'-dioxo acetic acid compound and preparation method thereof
  • Kudzu-vine root daidzein-7, 4'-dioxo acetic acid compound and preparation method thereof
  • Kudzu-vine root daidzein-7, 4'-dioxo acetic acid compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: Preparation of daidzein-7,4'-dioxoacetic acid

[0030] In a 500ml round bottom flask, add 2.54g of Pueraria daidzein, 2.80g of anhydrous potassium carbonate, 3.32g of potassium iodide, and 3.66g of ethyl chloroacetate, add it to 100ml of anhydrous acetone, reflux for 8 hours, distill off the acetone, wash with water, Filter and dry; take the above compound and dissolve it in 30ml of absolute ethanol, add an equimolar amount of 1mol / L HCL, reflux for 5 hours, filter and dry to obtain a white powder, recrystallize with 80% ethanol to obtain mp274.91 °C, 3.33 g of white flaky crystals, yield 90%.

Embodiment 2

[0031] Embodiment 2: Preparation of daidzein-7,4'-sodium dioxoacetate

[0032] In a 500ml round bottom flask, add 2.54g of kudzu root daidzein, 1.38g of anhydrous potassium carbonate, 3.32g of potassium iodide, 2.45g of ethyl chloroacetate, add 20ml of anhydrous N,N-dimethylformamide, 80°C React in a water bath for 10 hours, wash with water, filter, and dry; dissolve the above compound in absolute ethanol, add an equimolar amount of hydrochloric acid solution to obtain daidzein-7,4'-dioxoacetic acid, filter, and dry; The above compound was dissolved in 50ml of absolute ethanol, and an equimolar amount of sodium hydroxide solution was added dropwise, filtered, and dried to obtain 3.64g of white amorphous powder (mp>350°C), with a yield of 88%. UV(water): λmax=249nm, 302nm, IR(KBr)cm-1 : 3419.6(-OH), 1638(C=O); MS: [M-H] - : 368.7, [M+H] + : 370.9; 1 H-NMR: 4.41-4.85 (m, 4H), 6.77 (d, 1H), 6.90-6.93 (d, 2H), 6.95-6.99 (m, 1H), 7.24-7.27 (d, 2H), 7.83-7.86 (d, 1H), 7.92 (s, 1...

Embodiment 3

[0033] Embodiment 3: Preparation of daidzein-7,4'-ethyl dioxoacetate

[0034] In a 500ml round bottom flask, add 2.54g of kudzu root daidzein, 2.76g of anhydrous potassium carbonate, 0.25g of potassium iodide, and 7.35g of ethyl chloroacetate, add it to 100ml of anhydrous chloroform, react in a water bath at 70°C for 10h, wash with water, It was filtered and dried to obtain 3.62 g of white flaky crystals, mp=167.51° C., and the yield was 85%.

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Abstract

The invention belongs to the field of medical technology and relates to a kudzu-vine root daidzein-7, 4'-dioxo acetic acid compound and a preparation method thereof; the compound has the following formula, wherein R1 and R2 can be the same of different and are chosen from H, metal ions, organic cations, basic amino acid cations, C1-C10 alkyl group independently; R3 and R4 can be the same or different and are independently chosen from H or C1-C10 alkyl group; the kudzu-vine root daidzein-7, 4'-dioxo acetic acid compound, and a carrier or excipient which can be acceptable medically are combined to form medicine composite; the compound and the medicine composite has the advantages of cerebral ischemia resistance, oxygen-poor resistance, myocardial ischemia resistance, antagonistic dysmnesia resistance, platelet aggregation resistance and thrombopoiesis resistance and protecting rat cortical neuron damage caused by oxygen deficit.

Description

technical field [0001] The present invention relates to the technical field of medicine, and relates to daidzein-7,4'-dioxoacetic acid (DZV), a pharmaceutical composition containing the compound and its new medical application, especially the compound and its composition in Anti-cerebral ischemia, hypoxia, myocardial ischemia, hypoxia, antagonism memory impairment, anti-platelet aggregation and anti-thrombosis, and the application of drugs to protect rat cortical neuron damage caused by hypoxia. The present invention also relates to a synthetic method for preparing a water-soluble derivative pueraria daidzein-7,4'-dioxoacetic acid compound by utilizing the pueraria daidzein. Background technique [0002] Pueraria daidzein is an active ingredient of traditional Chinese medicine Pueraria lobata and soybean and other leguminous plants. It has been proved by a large number of pharmacological and clinical studies that it can significantly dilate coronary arteries, cerebral blood ...

Claims

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Application Information

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IPC IPC(8): C07D311/36A61K31/352A61P9/10A61P25/28A61P7/02A23L1/30A23L33/105
Inventor 王淑君
Owner SHENYANG PHARMA UNIVERSITY
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