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Beta-elemene amino acid or carboxylic acid derivatives and preparation process and use thereof

A technology of carboxylic acid derivatives and amino acids, applied in the application field of the β-elemene amino acid or carboxylic acid derivatives, can solve the problems of vascular irritation, difficulty in reaching the action site, poor water solubility of elemene and the like

Inactive Publication Date: 2006-10-11
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, elemene milk is used as a second-line anticancer drug in clinical practice. Its anticancer effect is weaker than that of 5-fluorouracil and cisplatin, and its effect on some solid tumors is not obvious.
Moreover, elemene has poor water solubility, and the clinically used dosage form is only emulsion, which has poor stability. Intravenous administration has obvious vascular irritation, and it is difficult to reach the site of action, which limits its clinical application.

Method used

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  • Beta-elemene amino acid or carboxylic acid derivatives and preparation process and use thereof
  • Beta-elemene amino acid or carboxylic acid derivatives and preparation process and use thereof
  • Beta-elemene amino acid or carboxylic acid derivatives and preparation process and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1 Chlorinated β-elemene intermediate and preparation of

[0032] Add 51.0g (0.25mol) of β-elemene and 35mL (0.61mol) of glacial acetic acid into a three-necked bottle equipped with a mechanical stirrer, cool to about 5°C with an ice-water bath, and pour the mixture from a constant-pressure dropping funnel under stirring. 180mL (1.41mol / L, 0.254mol) sodium hypochlorite solution was added dropwise, and the dropwise addition was completed in about 4h, and the reaction was continued for 1h. Then the reaction solution was transferred to a 1L separatory funnel, extracted twice with 50mL petroleum ether (60-90°C), the organic phases were combined, washed with water until neutral, and dried over anhydrous sodium sulfate. Concentration gave 52.5 g of light yellow-green oil, which was separated by silica gel column chromatography to obtain 20.5 g of monochloro-elemene, a mixture of 13-chloro-β-elemene and 14-chloro-β-elemene.

Embodiment 2

[0033] General method for the preparation of embodiment 2 amino acid methyl ester hydrochloride

[0034] Add 22mmol of amino acid and 15mL of dry methanol into a 100mL three-necked bottle equipped with a drying tube and tail gas absorption device, and quickly pass in dry hydrogen chloride gas under stirring at room temperature until the amino acid is completely dissolved, and then continue to pass in hydrogen chloride under heating and reflux 2h, concentrated to give a white solid. Recrystallized with 1:3 methanol-ether mixed solvent.

Embodiment 3

[0035] The preparation general method of embodiment 3 β-elemene amino acid methyl ester derivatives

[0036] Dissolve 10mmol of amine, 5mmol of monochlorinated β-elemene, and 10mmol of triethylamine in 5mL of N,N-dimethylformamide, and reflux for 8-20h. The resulting triethylamine hydrochloride needle crystals were filtered out, and the filtrate was added with 10 mL of water, extracted 4 times with petroleum ether-diethyl ether, the extract was dried and concentrated, and separated by thin-layer preparation with silica gel.

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Abstract

The invention discloses a A-elemene amino acid or carboxylic acid derivants, Process for preparing, usage and preparation; the structural formula of derivant is III. Wherein R represent C2-C20 every kinds of alpha-, beta-, gamma- amino acids; Every kinds of amino acids of C1-C20; wherein cyclohexane skeleton has three chirality center. This derivant is used to improve water-solubility and anticancer active of A-elemene amino acid, introducing amino acid which contains synthetic compounds of amidol or carboxy group, this derivant has stronger physiologically active and larger polarity, reaching the purpose of improving water-solubility.

Description

Technical field: [0001] The present invention relates to a new β-elemene amino acid or carboxylic acid derivative and a preparation method thereof, an intermediate for synthesizing the β-elemene amino acid or a carboxylic acid derivative and a preparation method thereof, and the β-elemene Use of elemene amino acid or carboxylic acid derivatives. Background technique: [0002] The β-elemene isolated from the volatile oil of Curcuma wenyujin Y.H.Chen et C.Ling (Curcuma wenyujin Y.H.Chen et C.Ling), also known as Wenzezhu, is the main component of the broad-spectrum anti-tumor drug elemene milk developed by my country. (Guo Yongmin, Wu Xiuying, Chen Yuren. Isolation and identification of elemene in the volatile oil of Ezhu [J]. Chinese Medicine Bulletin, 1983, 8(30): 31-33). β-Elemene has high selectivity to tumor cells, no myelosuppressive effect, no obvious liver and kidney toxicity, and has the "double effect" of selectively inhibiting tumor cell proliferation and improving ...

Claims

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Application Information

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IPC IPC(8): C07C229/00C07C69/03A61K31/198A61K31/401A61K31/405A61K31/215A61P35/00
Inventor 黄金华徐莉英王敏伟
Owner SHENYANG PHARMA UNIVERSITY
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