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Phytosterol phosphorylation amino-acid ester derivative and synthetic method thereof

A technology for phytosterol phosphorylation of amino acid esters and phosphorylated amino acids, which is applied in chemical instruments and methods, organic chemistry, steroids and other directions to achieve the effects of good oil solubility, high yield and simple raw materials

Active Publication Date: 2013-12-11
伊诺药物研究南京有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After esterification of phytosterols and N-phosphorylated amino acids, they are converted into sterol phosphorylated amino acid esters. No related reports have been seen so far.

Method used

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  • Phytosterol phosphorylation amino-acid ester derivative and synthetic method thereof
  • Phytosterol phosphorylation amino-acid ester derivative and synthetic method thereof
  • Phytosterol phosphorylation amino-acid ester derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of N-diisopropoxyphosphorylated alanine:

[0029] Weigh 1.78 g (20 mmol) of L-alanine into a 100 mL single-necked round bottom flask, add 5 mL each of water, ethanol, and triethylamine, cool to below 0°C, and add diisopropyl phosphite dropwise The mixture of 3.32 g (20 mmol) of ester and 15 mL of carbon tetrachloride was added dropwise within 30 minutes, then naturally rose to room temperature, and continued to stir for 5 hours. After the reaction, the solution was separated into layers, 30 mL of water was added, and low boiling point substances were evaporated under reduced pressure at 40°C to obtain a clear liquid, which was washed with petroleum ether, diethyl ether, and ethyl acetate (2×20 mL), and the aqueous phase was washed with 1mol / L The pH was adjusted to 3 with hydrochloric acid. Extracted with ethyl acetate (2×20 mL), combined the organic phases, washed 3 times with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent...

Embodiment 2

[0039] Synthesis of N-diisopropoxyphosphorylated tryptophan:

[0040] Weigh 2.85 g (15 mmol) of L-tryptophan into a 100 mL single-necked round bottom flask, add 4.0 mL each of water, ethanol, and triethylamine, and slowly add phosphorous acid to the above solution at 0 °C The mixed solution of 2.66 g (16 mmol) of diisopropyl ester and 10 mL of carbon tetrachloride was added dropwise within 30 minutes, then naturally rose to room temperature, and continued stirring for 5 hours. After the reaction, the solution was separated into layers, 25 mL of water was added, and low boiling point substances were evaporated at 40°C to obtain a clear liquid, which was washed with petroleum ether, diethyl ether, and ethyl acetate (2×20 mL), and the water phase was washed with 1mol / L hydrochloric acid Adjust the pH to 3. Extracted with ethyl acetate (2×20 mL), combined the organic phases, washed 3 times with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent at ...

Embodiment 3

[0050] Synthesis of N-diisopropoxyphosphorylated leucine:

[0051] Weigh 2.6 g (20 mmol) of L-leucine into a 100 mL single-necked round bottom flask, add 6.0 mL each of water, ethanol, and triethylamine, and slowly add phosphorous acid to the above solution at 0°C The mixed solution of 3.49 g (21 mmol) of diisopropyl ester and 12 mL of carbon tetrachloride was added dropwise within 30 minutes, then naturally rose to room temperature, and continued stirring for 5 hours. After the reaction, the solution was separated into layers, 25 mL of water was added, and low boiling point substances were evaporated at 40°C to obtain a clear liquid, which was washed with petroleum ether, diethyl ether, and ethyl acetate (2×20 mL), and the water phase was washed with 1mol / L hydrochloric acid Adjust the pH to 3. Extracted with ethyl acetate (2×20 mL), combined the organic phases, washed 3 times with saturated brine, dried over anhydrous sodium sulfate, and evaporated the solvent at 45°C to ...

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Abstract

The invention belongs to a phytosterol phosphorylation amino-acid ester derivative and a synthetic method thereof, belonging to the field of organic chemical synthesis. The synthetic method comprises the following steps of firstly, selecting different natural amino acids to generate phosphorylation reaction with a phosphorylation reagent to obtain N- phosphorylation amino acids; and then, directly mixing the phytosterol phosphorylation with the N- phosphorylation amino acids, and adding a catalyst and an organic solvent for reacting at 45 DEG C-85 DEG C to synthesize high-purity phytosterol phosphorylation amino-acid ester. The synthetic method is simple and convenient to operate, gentle in condition and high in conversation rate, and the used materials are easily available and low in price, so that the synthetic method is suitable for industrial production. The phytosterol phosphorylation amino-acid ester prepared by the synthetic method disclosed by the invention has good water solubility, and a part of compounds simultaneously have good water solubility and lipid solubility, so that a problem that the biological activity of the phytosterol phosphorylation is limited due to the limited solubility is solved. Moreover, the obtained product has the functional characteristics of lowering cholesterol, preventing and treating cardiovascular and cerebrovascular diseases, preventing oxidization and the like, and can be widely applied to a plurality of fields including food, medicines and cosmetics.

Description

technical field [0001] The invention relates to phytosterol phosphorylated amino acid ester derivatives and a synthesis method thereof, in particular to a method for synthesizing phytosterol phosphorylated amino acid ester derivatives by reacting with N-phosphorylated amino acids with phytosterol as a raw material. It belongs to the field of organic chemical synthesis. Background technique [0002] At present, cardiovascular and cerebrovascular diseases have become the "number one killer" of human health and life. According to the 2004 survey report on nutrition and health status of Chinese residents, the number of patients with dyslipidemia in my country is as high as 160 million, accounting for 18.6% of the total adult population in the country, of which 2.9% are hypercholesterolemia and 11.9% are hypertriglyceridemia. Low high density lipoproteinemia 7.4%. Dyslipidemia is a risk factor for cardiovascular and cerebrovascular diseases, and the main causes of dyslipidemia ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J51/00C07J75/00
Inventor 袁金伟买文鹏杨亮茹肖咏梅毛璞屈凌波
Owner 伊诺药物研究南京有限公司
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