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Beta-elemene amino acid derivatives as well as synthetic method and use thereof

A synthesis method and amino acid technology, which can be used in drug combinations, chemical instruments and methods, and medical preparations containing active ingredients, etc., can solve problems such as poor water solubility, limited clinical application, etc. efficacy, enhancing efficacy and bioavailability

Inactive Publication Date: 2008-07-23
SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

β-Elemene has been used clinically as a traditional Chinese medicine, but its clinical application is limited due to its extremely poor water solubility. Therefore, how to improve its water solubility has been attracting much attention

Method used

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  • Beta-elemene amino acid derivatives as well as synthetic method and use thereof
  • Beta-elemene amino acid derivatives as well as synthetic method and use thereof
  • Beta-elemene amino acid derivatives as well as synthetic method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Synthesis of β-elemene γ-butyric acid derivatives

[0029]

[0030] Add 0.1481g (1.4mmol) γ-butyric acid, 0.0609g NaOH, into 5mL CH 3 CH 2 OH and 1.6mL H 2 O, stirred at room temperature until completely dissolved, then added 0.64 g (2.7 mmol) of the chlorinated β-elemene mixture. Stir magnetically in an oil bath at 65°C, heat for 44 hours, the solution is transparent and blue, evaporate the solvent after the reaction is complete, and add CH 2 Cl 2 , use hydrochloric acid to adjust the pH value to 1~2, if no precipitation occurs, use CHCl 3 Extraction (10mL×3) gave a yellow oily liquid.

[0031] CH through a silica gel column 2 Cl 2 :CH 3 OH=10:1 (v / v) to separate the product, the developing agent is CH 2 Cl 2 :CH 3 When OH=5:1 (v / v), the Rf value of the product is 0.59.

[0032] Characterization: IR V max : 3080(C=C-H), 1709(C=O);

[0033] 1 H-NMR (CDCl 3 , TMS, 500MHz), δ0.99(s, 3H, CH 3 ), 1.20-1.79 (m, 6H), 1.70 (s, 3H, CH 3 ), 1.92-2....

Embodiment 2

[0035] Example 2 Synthesis of β-elemene β-alanine derivatives

[0036]

[0037] Add 0.1378g (1.5mmol) β-Ala, 0.1281g NaOH, 5mL CH 3 CH 2 OH and 1.8mL H 2 O, stirred at room temperature until completely dissolved, then added 0.70 g (3.0 mmol) of the chlorinated β-elemene mixture. Stir magnetically in an oil bath at 65°C, heat for 48 hours, the solution is transparent and yellow, evaporate the solvent after the reaction is complete, and add CH 2 Cl 2 , adjust the pH value to 1-2 with hydrochloric acid. If no precipitation occurs, use CHCl 3 Extraction (10mL×3) gave a yellow oily liquid.

[0038] CH through a silica gel column 2 Cl 2 :CH 3 OH=10:1 to separate the product, the developer is CH 2 Cl 2 :CH 3 When OH=5:1, the Rf value of the product is 0.59.

[0039] Characterization: IR V max : 3080(C=C-H), 1719(C=O), 1637(C=C);

[0040] 1 H-NMR (CDCl 3 , TMS, 500MHz), δ0.99(s, 3 H, CH 3 ), 1.20-1.35(m, 1H), 1.36-1.78(m, 5H), 1.73(s, 3H, CH 3 ), 1.99-2.19(m, 2H)...

Embodiment 3

[0043] Example 3 Synthesis of β-elemene L-alanine derivatives

[0044]

[0045] Add 0.7543g (8.4mmol) α-alanine, 0.5774g NaOH, 15mL CH 3 CH 2 OH and 5mL H 2 O, stirred at room temperature until completely dissolved, then added 4 g (16.8 mmol) of the chlorinated β-elemene mixture. Stir magnetically in an oil bath at 66°C, heat for 28 hours, the solution is transparent and yellow, evaporate the solvent after the reaction is complete, and add CH 2 Cl 2 , adjust the pH value to 1-2 with hydrochloric acid. If insoluble matter appeared, the solution was filtered to obtain a white solid with a yield of 57.4%.

[0046] Characterization: IR V max : 3080(C=C-H), 1637(C=O);

[0047] 1 H-NMR (CD 3 OD, TMS, 500MHz), δ0.99(s, 3H), 1.39-1.58(m, 6H), 1.59(d, J=6.07, 3H), 1.70(s, 3H), 2.01-2.10(m, 2H ), 3.59-3.63(m, 1H), 3.74-3.83(m, 2H), 4.57(s, 1H), 4.82(s, 1H), 4.89(s, 1H), 4.91(d, J=3.34, 1H ), 5.21 (s, 1H), 5.28 (s, 1H), 5.80 (dd, J=17.94, 10.9, 1H).

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Abstract

The invention discloses Beta-elemene amino acid derivatives as shown in the formula I and the salt accepted pharmaceutically, the synthesis method of the Beta-elemene amino acid derivatives and the usage in preparing anticancer drugs; wherein, in the formula I, R[1], R[2] are independently H or amino acid with one hydrogen atom substituted on amino; the condition is H when R[1] and R[2] are different. The synthesis method of the Beta-elemene amino acid derivatives in the formula I and the salt accepted pharmaceutically has the advantages of having good water soluble and biocompatibility and higher anticancer activity compared with Beta-elemene and an important reaction intermediate. The synthesis method can be used as synthesizing other Beta-elemene derivatives.

Description

technical field [0001] The invention relates to an anticancer drug, in particular to a beta-elemene amino acid derivative and its synthesis method and application. Background technique [0002] Cancer is a common disease that seriously endangers people's lives and health. β-elemene (β-Elemene) is the first anti-cancer active ingredient extracted from the rhizome of Zingiberaceae plant Wen Curcuma (Wen Curcuma) in recent years. Its molecular formula is C 15 h 24 , the structural formula is as follows: [0003] [0004] Dong Jinhua etc. have reported a series of β-elemene anticancer compounds (Dong Jinhua, the research of β-elemene series anticancer compounds, doctoral dissertation of Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 1995); CN1462745 patent application discloses β - Elemene pyrimidine derivatives; CN1462746 discloses β-elemene five-membered nitrogen heterocyclic derivatives and its synthesis method; CN1153168 patent discloses elemene hydr...

Claims

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Application Information

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IPC IPC(8): C07C229/14C07C229/34C07C229/22C07C229/38C07C227/16A61K31/197A61K31/198A61P35/00
Inventor 沈玉梅成康民刘贵锋任云峰孙艳红王谋华
Owner SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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