Azo hetercyle beta-elemene derivative and its preparation method and uses

A technology of elemenamide and derivatives is applied in the application field of the nitrogen-containing heterocyclic β-elemene derivatives to achieve the effects of good water solubility, high biological activity and improved biological activity

Inactive Publication Date: 2006-02-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent CN 1153168; Chinese patent CN 1462745, 2003; Chinese patent CN 1462746, 2003; Chinese patent CN 1153167, 1997; Zhou Hongyu, etc., research progress on the mechanism of elemene's anti-tumor action, Chinese tumor

Method used

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  • Azo hetercyle beta-elemene derivative and its preparation method and uses
  • Azo hetercyle beta-elemene derivative and its preparation method and uses
  • Azo hetercyle beta-elemene derivative and its preparation method and uses

Examples

Experimental program
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Effect test

example 1

[0057] The preparation of example 1β-elemene piperazine intermediate

[0058] 1) Put 20.4g (0.1mol) of β-elemene into a 500ml jacketed three-necked bottle with a thermometer, add 9g (0.15mol) of glacial acetic acid and 80ml of dichloromethane. The reaction solution was cooled to 0-5°C, and 148 g of NaOCl aqueous solution was added dropwise. After reacting for 8h, the organic layer was separated, the aqueous layer was saturated with NaHCO3, extracted with ether (2×70ml), the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed in vacuum on a water bath to obtain a light yellow oily liquid which was the monochlorinated product of β-elemene as two isomers with a content of 48.7%. Fast column separation to obtain a monochlorinated mixture of two isomers, which can be used for the next reaction without separation.

[0059] 2) Dissolve 0.86g (0.01mol) of piperazine in 20ml of dichloromethane, place in a jacketed bottle, cool to -10--5°C, protect with a...

example 2

[0062] The general synthetic method of example 2 nitrogen-containing heterocyclic β-elemenamide derivatives

[0063] The 4th) step product β-elemene piperazine intermediate and triethylamine in embodiment 1 are mixed with the dichloromethane mixed solution of 0.5mol / l, get this solution 2ml, shake at room temperature half an hour, cooling reaction system to 0-5°C. Add 2ml of 0.5mol / l acid chloride. After the reaction, 3ml of saturated NaHCO3 aqueous solution was added, shaken at room temperature for 30min, and the organic layer was separated. The organic layer was washed with water 3×3ml. Anhydrous Na2SO4 drying, vacuum precipitation, the product was obtained.

Embodiment 3

[0064] Example 3 General Synthetic Method of Nitrogen-Containing Heterocyclic β-Elemene Alkyl Derivatives

[0065] The 4th in embodiment 1) step product β-elemene piperazine intermediate and triethylamine are mixed with the toluene mixed solution of 0.5mol / l, get this solution 2ml, add the aryl chloride of 0.5mol / l or Aryl bromide 2ml. Heated to reflux for 24 hours. After the reaction, 3ml of saturated NaHCO3 aqueous solution was added, shaken at room temperature for 30min, and the organic layer was separated. The organic layer was washed with water 3×3ml. Anhydrous Na2SO4 drying, vacuum precipitation, the product was obtained.

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Abstract

The invention provides beta-elemene polyamide derivatives containing phthalazinone having the structural features disclosed in the specification. The invention discloses a high-activity beta-elemene derivative with novel structures, thus can be used for preparing medicaments containing beta-elemene derivatives with better curative effects.

Description

Technical field: [0001] The present invention relates to a new nitrogen-containing heterocyclic β-elemene derivative and a preparation method thereof, an intermediate for synthesizing the nitrogen-containing heterocyclic β-elemene derivative and a preparation method thereof, and the nitrogen-containing Applications of heterocyclic β-elemene derivatives. Background technique: [0002] β-elemene is the main component of elemene extracted from the Chinese herbal medicine Curcumae. It is a national second-class non-cytotoxic anti-tumor drug independently developed by our country. At present, the elemene emulsion with β-elemene as the main component has been approved by the Ministry of Health as a "Class II New Drug of Western Medicine" and is suitable for Phase III clinical trials. However, the systematic research on its derivatives has not made great progress due to the difficulty in isomer separation. (Vig, O.P. Ram Bhagat; Atwal, K.S.; Bari, S.S.J. Indian Chem. Soc., 1975,...

Claims

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Application Information

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IPC IPC(8): C07D295/16C07D213/82C07D265/02A61K31/496A61P35/00
Inventor 万伯顺肖远胜梁鑫淼吴凡
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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