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Stearoyl amino acid compound, and preparation method and applications thereof

A technology of fatty acyl amino acids and compounds, applied in the field of medicine, can solve the problem of no compound antioxidant effect, achieve significant antioxidant activity, and have broad application prospects

Inactive Publication Date: 2015-05-13
SHANGHAI JIAOTONG UNIV SCHOOL OF MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, prior to the present invention, there have been no published reports of the compounds of the present invention being used for their antioxidant effects

Method used

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  • Stearoyl amino acid compound, and preparation method and applications thereof
  • Stearoyl amino acid compound, and preparation method and applications thereof
  • Stearoyl amino acid compound, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation of embodiment 1N-stearyl amino acid

[0048] (1) Protection of amino acids - carboxymethyl esterification

[0049] Amino acid reacts with hydrochloric acid-methanol to obtain amino acid methyl ester. Stearic acid and thionyl chloride are heated to reflux to obtain stearyl chloride.

[0050] Amino acid methyl ester was dissolved in pyridine, the above stearyl chloride was added dropwise, and the reaction was stirred overnight. After extraction, recrystallization, etc., stearyl amino acid methyl ester is obtained. Then it is hydrolyzed under alkaline conditions to obtain stearyl amino acid.

[0051]

[0052] (2) Amino acid deprotection - first activation of stearic acid (active ester method)

[0053] Stearic acid (SA) reacts with N-hydroxysuccinimide (N-HOSu) to generate activated ester, and then reacts with amino acid compounds to obtain stearamide.

[0054] Stearic acid and N-hydroxysuccinimide were stirred and reacted for 16 hours under the acti...

Embodiment 2

[0069] The preparation of embodiment 2N-stearyl amino acid

[0070] In this example, N-stearyl amino acid is prepared by a one-pot method. The one-pot method has mild reaction conditions, is not limited by amino acid solubility and system pH, and has ideal yield and purity. The following takes the one-pot preparation of N-stearyl tyrosine (NSTyr) as an example to describe the reaction steps of the one-pot method in detail.

[0071] At room temperature, with 1-hydroxybenzotriazole HOBT as coupling agent, 4-dimethylaminopyridine DMAP as catalyst, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride in One-pot synthesis of N-stearyl tyrosine methyl ester under alkaline conditions with pre-synthesized L-tyrosine methyl ester, which was hydrolyzed to N-stearyl tyrosine (NSTyr).

[0072]

[0073] 1. Preparation of Tyrosine Methyl Ester

[0074] One side of a 25ml two-necked bottle was connected to a drying tube, and the other was connected to a dropping funnel, and 5ml of...

Embodiment 3

[0077] Example 3 Structure identification

[0078] The stearyl amino acid compound that above-mentioned embodiment 1 synthesizes all passes through 1 PHNMR, 13 PCNMR identified its structure. The structural identification data of compounds 6 and 11 are listed below.

[0079] Compound 6:

[0080] White solid, mp, 106-108°C. 1HNMR (500MHz, CDCl3, TMS) δppm: 7.0 (2H, d, J=10.2Hz, H on the benzene ring); 6.7 (2H, d, J=10.5Hz, H on the benzene ring); 5.9 (1H, s, -NH-); 4.8 (1H, m, -CH-NH-); 3.1 (2H, m, -CH2-), 2.17 (2H, t, -CH2-CONH-); 1.4 (2H, m, -CH2-); 1.26 (28H, m, -(CH2)n-); 0.88 (3H, t, -CH3). 13CNMR (500MHz, CDCl3) δppm: 174.1 (-CONH-); 173.9 (-COOH); 155.3 (C of -OH on the benzene ring); 130.5, 130.3, 127.6, 121.8 and 115.8 (the other 5 C on the benzene ring ); 53.4 (-CH-NH-); 36.8 (-CH2-CONH-); 36.6 (-CH2-CHNH-); 32.0 (-CH2-); 31.6~22.6 (14×-CH2-); 14.0 (- CH3-).

[0081] The above data confirm that the compound is N-stearyl tyrosine.

[0082] Compound 11:

[00...

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Abstract

The invention discloses a stearoyl amino acid compound. The stearoyl amino acid compound possesses antioxidant activity, and is represented by formula (I); R1 is used for representing H or C1-6 linear alkyl or C1-6 branched alkyl, wherein the C1-6 linear alkyl or the C1-6 branched alkyl can be substituted by one or a plurality of substituent groups, and the substituent groups are selected from hydroxyl, amino, sulfydryl, carboxyl, aryl, acylamino, alkyl sulphanyl, or five-member heterocycle or seven-member heterocycle with 1 to 2 nitrogen atoms; R2 is used for representing H or C1-4 alkyl; and R3 is used for representing C11-25 saturated aliphatic hydrocarbon or unsaturated aliphatic hydrocarbon. The invention also discloses a preparation method and applications of the stearoyl amino acid compound. The stearoyl amino acid compound is capable of preventing glutamic acid induced cell oxidative damage, possesses excellent antioxidant activity, can be used for preparing antioxidants, and possesses a promising application prospect.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a stearyl amino acid compound with antioxidant activity, a preparation method and application thereof. Background technique [0002] N-stearyl amino acids (NSAs) are amide compounds formed by combining the carboxyl group of stearic acid with the α-amino group of amino acid. As early as the 1950s and 1960s, there were literatures reporting its synthesis method. In recent years, there are also research reports on its pharmacological activity, but there is no research report on the antioxidant effect of such compounds. [0003] (1) Synthesis method of NSAs [0004] In the synthesis of NSAs, stearic acid is generally made into stearyl chloride to improve the activity of the acylation reaction; amino acid is reacted with hydrochloric acid-methanol to obtain amino acid methyl ester to protect the carboxyl group. Then stearyl chloride and amino acid methyl ester undergo acylation re...

Claims

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Application Information

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IPC IPC(8): C07C233/47C07C231/02C07D207/16C07C323/59C07C319/12C07D233/64C07D209/20A61K31/223A61K31/216A61K31/198A61K31/401A61K31/4172A61K31/405A61P39/06
Inventor 陆阳刘坚华殷莎杨锐刘沙颜君杰乐可佳唐双奇
Owner SHANGHAI JIAOTONG UNIV SCHOOL OF MEDICINE
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