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Macamides compound and synthetic method and application thereof

The technology of a macamide and a synthesis method, which is applied in the field of medicine, can solve the problem that a macamide monomer compound cannot be prepared in large quantities, and achieves the effects of low price, few by-products, and low toxicity

Inactive Publication Date: 2017-11-17
INST OF AGRO PROD PROCESSING SCI & TECH SICHUAN ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to provide a kind of macamide compound and its synthetic method, application, it aims at improving the problem that existing macamide monomer compound cannot be produced in large quantities

Method used

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  • Macamides compound and synthetic method and application thereof
  • Macamides compound and synthetic method and application thereof
  • Macamides compound and synthetic method and application thereof

Examples

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[0029] A method for synthesizing macamide, comprising: catalyzing and oxidizing linoleic acid and an oxidant to obtain a macaene mixture through pyridine derivatives; performing amidation reaction of the macaene mixture with benzylamine or benzylamine derivatives, and then separating by preparative chromatography;

[0030] Wherein: the oxidizing agent is any one of 2,2,6,6-tetramethylpiperidine-nitrogen-oxide, tribromopyridinium, and 2-iodylbenzoic acid. Benzylamine derivatives are 3-methoxybenzylamine or 3,4-dimethoxybenzylamine.

[0031] Linoleic acid, molecular formula: CH 3 (CH 2 ) 4 CH=CHCH 2 CH=CH(CH 2 ) 7 COOH; a kind of unsaturated fatty acid, colorless to pale yellow liquid, changes color when exposed to air.

[0032] TEMPO, tetramethylpiperidine nitrogen oxide; 2,2,6,6-tetramethylpiperidine-nitrogen-oxide; English name: 2,2,6,6-Tetramethyl-1-piperidinyloxy; Molecular formula: C 9 h 18 NO.

[0033] Py.HBr3 tribromopyridinium; English name: pyridinium hydrobro...

Embodiment 1

[0071] This embodiment provides a macamide compound, which is synthesized by the following steps:

[0072] Weigh 1g of linoleic acid and dissolve it in 20ml of acetonitrile, add 0.5g of 4-dimethylaminopyridine (DMAP) as a catalyst, then add 1.6g of TEMPO, react at room temperature for 4h, concentrate under reduced pressure at 30°C to remove acetonitrile, and wash the residue with 20ml of dimethicone Methane chloride was dissolved, and the filtrate was washed three times with saturated sodium carbonate solution and water successively, and concentrated under reduced pressure at 30°C to remove methylene chloride to obtain a macaene mixture.

[0073] Take 0.03mol of benzylamine and 0.02mol of the above-mentioned macaene mixture, add 50ml of dry dichloromethane, add 0.03mol of 4-dimethylaminopyridine, stir for 20min; then add 0.03mol of N,N'-cyclohexylcarbodiimide, The reaction was stirred at room temperature for 3 h, and filtered; the filtrate was washed with saturated sodium carb...

Embodiment 2

[0075] This embodiment provides a macamide compound, which is synthesized by the following steps:

[0076] Weigh 1g of linoleic acid and dissolve it in 20ml of acetonitrile, add 0.5g of 4-pyrrolidinylpyridine as a catalyst, then add 1.6g of TEMPO, react at room temperature for 4h, concentrate under reduced pressure at 30°C to remove acetonitrile, and dissolve the residue in 20ml of dichloromethane. The filtrate was washed successively with saturated sodium carbonate solution and water three times, and concentrated under reduced pressure at 30°C to remove dichloromethane to obtain a macaene mixture.

[0077] Take 0.03mol 3,4-dimethoxybenzylamine and 0.02mol of the above-mentioned macaene mixture, add 50ml of dry dichloromethane, add 0.03mol 4-pyrrolidinylpyridine, stir for 20min; then add 0.03mol N, N' -Dicyclohexylcarbodiimide, stirred and reacted at room temperature for 3h, filtered; the filtrate was washed with saturated sodium carbonate solution and water three times in seq...

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Abstract

The invention relates to the field of drugs, in particular to a macamides compound and a synthetic method and application thereof. The synthetic method of macamides comprises the steps that linoleic acid and an oxidizing agent are subjected to catalytic oxidation through pyridine derivatives to obtain a macaenes mixture; the macaenes mixture and benzylamine or benzylamine derivatives are subjected to amidation and then separated through preparative chromatography, wherein the oxidizing agent is one of 2,2,6,6-tempol-nitrogen-oxide, pyridinium tribromide, 2-Iodoxybenzoic acid; the benzylamine derivatives are 3-trimethoprim or 3,4-dimethoxybenzamine. Linoleic acid is adopted as a starting reactant to be synthesized, and compared with the prior art that mecamide is extracted from plant maca, the needed raw material is low in cost and easy to obtain; in addition, in the synthesis preparation process, operation is easy, few by-products are produced, the needed reagents and solvents are small in toxicity and easy to obtain, and the novel path is provided for preparing a large number of macamides monomeric compounds.

Description

technical field [0001] The invention relates to the field of medicines, in particular to a macamide compound and its synthesis method and application. Background technique [0002] Maca (Lepidium meyenii Walp.) belongs to the genus Lepidium L. of the Brassicaceae family. It is a 1-year or 2-year-old herbaceous plant, native to the Andes mountains above 3500m above sea level in Peru, and can grow in extremely harsh environments. Maca is rich in protein, amino acid, polysaccharide, dietary fiber, vitamins, minerals and other nutrients, as well as various secondary metabolites such as glucosinolate, macaene and macamide, among which macamide is unique to maca some. Maca is rich in nutrients and has various effects such as improving fertility, improving sexual function, anti-fatigue, anti-osteoporosis, anti-oxidation, anti-cancer and protecting nerves. As people study on the biological activity and functional health care application of macamides, the preparation of macamide m...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C235/76A61P39/00A61P25/28A61P15/00A61P19/10
CPCC07C51/373C07C231/02C07C235/76C07C59/76
Inventor 夏陈陈建邓俊琳
Owner INST OF AGRO PROD PROCESSING SCI & TECH SICHUAN ACAD OF AGRI SCI
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